Flights from Toronto (YTZ)

Discover more affordable routes and cheaper dates from Toronto (YTZ) within a date range.

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CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:30pm - 3:12pm
Sun Oct 26th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 3 nights

Sun Oct 26th 2025 Porter Airlines · PD 2388 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 14th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 14th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 10 nights

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 29 nights

Thu Nov 20th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 28 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Fri Sep 26th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 7 nights

Fri Sep 26th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:55pm - 3:37pm
Sat Nov 15th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 23 nights

Sat Nov 15th 2025 Porter Airlines · PD 2388 Depart at 12:55pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:37pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Oct 6th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:55pm - 3:37pm
Sat Nov 15th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Oct 6th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 39 nights

Sat Nov 15th 2025 Porter Airlines · PD 2388 Depart at 12:55pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:37pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 14th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 14th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 63 nights

Mon Nov 17th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:15pm - 7:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 7 nights

Wed Oct 29th 2025 Porter Airlines · PD 2394 Depart at 5:15pm from Chicago (MDW) Fly for 1h 42m Arrive at 7:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:55pm - 3:37pm
Sat Nov 15th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 44 nights

Sat Nov 15th 2025 Porter Airlines · PD 2388 Depart at 12:55pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:37pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Sun Sep 28th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 28th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 50 nights

Mon Nov 17th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 14th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Wed Oct 1st 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 14th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 16 nights

Wed Oct 1st 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:55pm - 3:37pm
Sat Nov 15th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 57 nights

Sat Nov 15th 2025 Porter Airlines · PD 2388 Depart at 12:55pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:37pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Sep 15th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:55pm - 3:37pm
Sat Nov 15th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Sep 15th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 60 nights

Sat Nov 15th 2025 Porter Airlines · PD 2388 Depart at 12:55pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:37pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Oct 6th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Oct 6th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 22 nights

Wed Oct 29th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:15pm - 7:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 27 nights

Wed Oct 29th 2025 Porter Airlines · PD 2394 Depart at 5:15pm from Chicago (MDW) Fly for 1h 42m Arrive at 7:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Sep 4th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Fri Sep 26th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Sep 4th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 22 nights

Fri Sep 26th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 6 nights

Wed Oct 29th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Oct 6th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:15pm - 7:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Oct 6th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 23 nights

Wed Oct 29th 2025 Porter Airlines · PD 2394 Depart at 5:15pm from Chicago (MDW) Fly for 1h 42m Arrive at 7:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Sep 4th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Fri Sep 26th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Sep 4th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 22 nights

Fri Sep 26th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 26 nights

Mon Nov 17th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 14th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Thu Oct 16th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 14th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 31 nights

Thu Oct 16th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Fri Sep 5th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 5th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 73 nights

Mon Nov 17th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Oct 22nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Oct 22nd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 25 nights

Mon Nov 17th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 14th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 14th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 66 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Oct 21st 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Oct 21st 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 8 nights

Wed Oct 29th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 5 nights

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 27 nights

Wed Oct 29th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Oct 21st 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Oct 21st 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 27 nights

Mon Nov 17th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Tue Sep 23rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Wed Oct 1st 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 23rd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 7 nights

Wed Oct 1st 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Wed Oct 29th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 40 nights

Wed Oct 29th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Oct 6th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Oct 6th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 45 nights

Thu Nov 20th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 46 nights

Mon Nov 17th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Oct 6th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Oct 6th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 41 nights

Mon Nov 17th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Oct 6th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Oct 6th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 42 nights

Mon Nov 17th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Sep 15th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Sep 15th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 9 nights

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 59 nights

Mon Nov 17th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Sep 4th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Sep 4th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 20 nights

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 46 nights

Mon Nov 17th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Sep 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 22 nights

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 61 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Sep 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Wed Oct 1st 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 29 nights

Wed Oct 1st 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Wed Oct 1st 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 11 nights

Wed Oct 1st 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Fri Sep 5th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 5th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 19 nights

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Oct 6th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:30pm - 3:12pm
Sun Oct 26th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Oct 6th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 19 nights

Sun Oct 26th 2025 Porter Airlines · PD 2388 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Wed Sep 3rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Sep 3rd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 21 nights

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Fri Oct 3rd 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 14 nights

Fri Oct 3rd 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Tue Sep 23rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 24th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 23rd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 1 night

Wed Sep 24th 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:30pm - 3:12pm
Sun Oct 26th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 37 nights

Sun Oct 26th 2025 Porter Airlines · PD 2388 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Fri Sep 19th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Fri Sep 19th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 62 nights

Thu Nov 20th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 28th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Thu Oct 16th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 28th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 17 nights

Thu Oct 16th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 28th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Wed Oct 1st 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 28th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 2 nights

Wed Oct 1st 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Sun Sep 28th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 28th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 52 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 49 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Fri Oct 3rd 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 1 night

Fri Oct 3rd 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:30pm - 3:12pm
Sun Oct 26th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 24 nights

Sun Oct 26th 2025 Porter Airlines · PD 2388 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Oct 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Oct 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 49 nights

Thu Nov 20th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Sun Sep 28th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Thu Oct 16th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 28th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 18 nights

Thu Oct 16th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Sun Sep 28th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sun Sep 28th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 53 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Sep 15th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Sep 15th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 65 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Sep 15th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Wed Oct 1st 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Sep 15th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 15 nights

Wed Oct 1st 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Mon Sep 15th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Thu Oct 16th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Mon Sep 15th 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 30 nights

Thu Oct 16th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Sep 4th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Sep 4th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 77 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Sep 4th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Wed Oct 1st 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Sep 4th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 27 nights

Wed Oct 1st 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Thu Sep 4th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Fri Sep 5th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Thu Sep 4th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 1 night

Fri Sep 5th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Sep 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 79 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Sep 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Thu Oct 16th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 44 nights

Thu Oct 16th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Sep 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Wed Sep 3rd 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 1 night

Wed Sep 3rd 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$171

7:30am - 8:19am
Tue Sep 2nd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Fri Sep 5th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Tue Sep 2nd 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 3 nights

Fri Sep 5th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Sat Oct 11th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Thu Oct 16th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sat Oct 11th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 5 nights

Thu Oct 16th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

7:30am - 8:19am
Sat Oct 11th 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Sat Oct 11th 2025 Porter Airlines · PD 2387 Depart at 7:30am from Toronto (YTZ) Fly for 1h 49m Arrive at 8:19am in Chicago (MDW)

Stay in Chicago for 40 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Sep 3rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

9:15am - 11:57am
Thu Sep 11th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Sep 3rd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 7 nights

Thu Sep 11th 2025 Porter Airlines · PD 2388 Depart at 9:15am from Chicago (MDW) Fly for 1h 42m Arrive at 11:57am in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Sep 3rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:35pm - 8:17pm
Mon Nov 17th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Sep 3rd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 75 nights

Mon Nov 17th 2025 Porter Airlines · PD 2394 Depart at 5:35pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:17pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Sep 3rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

12:55pm - 3:37pm
Sat Nov 15th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Sep 3rd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 72 nights

Sat Nov 15th 2025 Porter Airlines · PD 2388 Depart at 12:55pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:37pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Sep 3rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

11:15am - 1:57pm
Thu Nov 20th 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Sep 3rd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 77 nights

Thu Nov 20th 2025 Porter Airlines · PD 2388 Depart at 11:15am from Chicago (MDW) Fly for 1h 42m Arrive at 1:57pm in Toronto (YTZ)
CA$171

3:35pm - 4:24pm
Wed Sep 3rd 2025

1h 49m
Toronto (YTZ) → Chicago (MDW)

Direct

5:20pm - 8:02pm
Fri Oct 3rd 2025

1h 42m
Chicago (MDW) → Toronto (YTZ)

Direct

Wed Sep 3rd 2025 Porter Airlines · PD 2393 Depart at 3:35pm from Toronto (YTZ) Fly for 1h 49m Arrive at 4:24pm in Chicago (MDW)

Stay in Chicago for 30 nights

Fri Oct 3rd 2025 Porter Airlines · PD 2394 Depart at 5:20pm from Chicago (MDW) Fly for 1h 42m Arrive at 8:02pm in Toronto (YTZ)
CA$178

9:45am - 11:15am
Wed Jun 18th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

6:50am - 8:30am
Fri Jun 20th 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Wed Jun 18th 2025 Porter Airlines · PD 2127 Depart at 9:45am from Toronto (YTZ) Fly for 1h 30m Arrive at 11:15am in New York (EWR)

Stay in New York for 1 night

Fri Jun 20th 2025 Porter Airlines · PD 2118 Depart at 6:50am from New York (EWR) Fly for 1h 40m Arrive at 8:30am in Toronto (YTZ)
CA$178

12:50pm - 2:20pm
Thu Jun 19th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

10:00am - 11:40am
Sun Jun 22nd 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Thu Jun 19th 2025 Porter Airlines · PD 2133 Depart at 12:50pm from Toronto (YTZ) Fly for 1h 30m Arrive at 2:20pm in New York (EWR)

Stay in New York for 2 nights

Sun Jun 22nd 2025 Porter Airlines · PD 2124 Depart at 10:00am from New York (EWR) Fly for 1h 40m Arrive at 11:40am in Toronto (YTZ)
CA$178

12:50pm - 2:20pm
Wed Jun 18th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

6:50am - 8:30am
Fri Jun 20th 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Wed Jun 18th 2025 Porter Airlines · PD 2133 Depart at 12:50pm from Toronto (YTZ) Fly for 1h 30m Arrive at 2:20pm in New York (EWR)

Stay in New York for 1 night

Fri Jun 20th 2025 Porter Airlines · PD 2118 Depart at 6:50am from New York (EWR) Fly for 1h 40m Arrive at 8:30am in Toronto (YTZ)
CA$178

2:00pm - 3:30pm
Thu Jun 19th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

11:00am - 12:40pm
Sun Jun 22nd 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Thu Jun 19th 2025 Porter Airlines · PD 2135 Depart at 2:00pm from Toronto (YTZ) Fly for 1h 30m Arrive at 3:30pm in New York (EWR)

Stay in New York for 2 nights

Sun Jun 22nd 2025 Porter Airlines · PD 2126 Depart at 11:00am from New York (EWR) Fly for 1h 40m Arrive at 12:40pm in Toronto (YTZ)
CA$178

2:00pm - 3:30pm
Wed Jun 18th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

6:50am - 8:30am
Fri Jun 20th 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Wed Jun 18th 2025 Porter Airlines · PD 2135 Depart at 2:00pm from Toronto (YTZ) Fly for 1h 30m Arrive at 3:30pm in New York (EWR)

Stay in New York for 1 night

Fri Jun 20th 2025 Porter Airlines · PD 2118 Depart at 6:50am from New York (EWR) Fly for 1h 40m Arrive at 8:30am in Toronto (YTZ)
CA$178

9:45am - 11:15am
Wed Jun 18th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

3:05pm - 4:45pm
Fri Jun 20th 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Wed Jun 18th 2025 Porter Airlines · PD 2127 Depart at 9:45am from Toronto (YTZ) Fly for 1h 30m Arrive at 11:15am in New York (EWR)

Stay in New York for 2 nights

Fri Jun 20th 2025 Porter Airlines · PD 2134 Depart at 3:05pm from New York (EWR) Fly for 1h 40m Arrive at 4:45pm in Toronto (YTZ)
CA$178

9:45am - 11:15am
Wed Jun 18th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

7:40pm - 9:20pm
Fri Jun 20th 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Wed Jun 18th 2025 Porter Airlines · PD 2127 Depart at 9:45am from Toronto (YTZ) Fly for 1h 30m Arrive at 11:15am in New York (EWR)

Stay in New York for 2 nights

Fri Jun 20th 2025 Porter Airlines · PD 2144 Depart at 7:40pm from New York (EWR) Fly for 1h 40m Arrive at 9:20pm in Toronto (YTZ)
CA$178

5:15pm - 6:45pm
Wed Jun 18th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

8:55am - 10:35am
Fri Jun 20th 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Wed Jun 18th 2025 Porter Airlines · PD 2141 Depart at 5:15pm from Toronto (YTZ) Fly for 1h 30m Arrive at 6:45pm in New York (EWR)

Stay in New York for 1 night

Fri Jun 20th 2025 Porter Airlines · PD 2122 Depart at 8:55am from New York (EWR) Fly for 1h 40m Arrive at 10:35am in Toronto (YTZ)
CA$178

3:00pm - 4:30pm
Thu Jun 19th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

12:00pm - 1:40pm
Sun Jun 22nd 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Thu Jun 19th 2025 Porter Airlines · PD 2131 Depart at 3:00pm from Toronto (YTZ) Fly for 1h 30m Arrive at 4:30pm in New York (EWR)

Stay in New York for 2 nights

Sun Jun 22nd 2025 Porter Airlines · PD 2128 Depart at 12:00pm from New York (EWR) Fly for 1h 40m Arrive at 1:40pm in Toronto (YTZ)
CA$178

2:00pm - 3:30pm
Wed Jun 18th 2025

1h 30m
Toronto (YTZ) → New York (EWR)

Direct

3:05pm - 4:45pm
Fri Jun 20th 2025

1h 40m
New York (EWR) → Toronto (YTZ)

Direct

Wed Jun 18th 2025 Porter Airlines · PD 2135 Depart at 2:00pm from Toronto (YTZ) Fly for 1h 30m Arrive at 3:30pm in New York (EWR)

Stay in New York for 1 night

Fri Jun 20th 2025 Porter Airlines · PD 2134 Depart at 3:05pm from New York (EWR) Fly for 1h 40m Arrive at 4:45pm in Toronto (YTZ)
CA$363

7:00am - 7:58am
Fri Jun 20th 2025

0h 58m
Toronto (YTZ) → Ottawa (YOW)

Direct

9:20pm - 10:22pm
Sun Jun 22nd 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 20th 2025 Porter Airlines · PD 2205 Depart at 7:00am from Toronto (YTZ) Fly for 0h 58m Arrive at 7:58am in Ottawa (YOW)

Stay in Ottawa for 2 nights

Sun Jun 22nd 2025 Porter Airlines · PD 2262 Depart at 9:20pm from Ottawa (YOW) Fly for 1h 2m Arrive at 10:22pm in Toronto (YTZ)
CA$402

4:05pm - 5:03pm
Fri Aug 8th 2025

0h 58m
Toronto (YTZ) → Ottawa (YOW)

Direct

9:35am - 10:37am
Sun Aug 10th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Aug 8th 2025 Air Transat · TS 7371 Depart at 4:05pm from Toronto (YTZ) Fly for 0h 58m Arrive at 5:03pm in Ottawa (YOW)

Stay in Ottawa for 1 night

Sun Aug 10th 2025 Air Transat · TS 7476 Depart at 9:35am from Ottawa (YOW) Fly for 1h 2m Arrive at 10:37am in Toronto (YTZ)
CA$827

10:20am - 11:15am
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

10:30am - 11:32am
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7706 Depart at 10:20am from Toronto (YTZ) Fly for 0h 55m Arrive at 11:15am in Ottawa (YOW)

Stay in Ottawa for 1 night

Sun Jun 8th 2025 Air Canada · AC 7709 Depart at 10:30am from Ottawa (YOW) Fly for 1h 2m Arrive at 11:32am in Toronto (YTZ)
CA$827

8:50am - 9:45am
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

10:30am - 11:32am
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7704 Depart at 8:50am from Toronto (YTZ) Fly for 0h 55m Arrive at 9:45am in Ottawa (YOW)

Stay in Ottawa for 2 nights

Sun Jun 8th 2025 Air Canada · AC 7709 Depart at 10:30am from Ottawa (YOW) Fly for 1h 2m Arrive at 11:32am in Toronto (YTZ)
CA$827

7:20pm - 8:15pm
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

7:35pm - 8:37pm
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7712 Depart at 7:20pm from Toronto (YTZ) Fly for 0h 55m Arrive at 8:15pm in Ottawa (YOW)

Stay in Ottawa for 1 night

Sun Jun 8th 2025 Air Canada · AC 7713 Depart at 7:35pm from Ottawa (YOW) Fly for 1h 2m Arrive at 8:37pm in Toronto (YTZ)
CA$827

7:20pm - 8:15pm
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

5:35pm - 6:37pm
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7712 Depart at 7:20pm from Toronto (YTZ) Fly for 0h 55m Arrive at 8:15pm in Ottawa (YOW)

Stay in Ottawa for 1 night

Sun Jun 8th 2025 Air Canada · AC 7711 Depart at 5:35pm from Ottawa (YOW) Fly for 1h 2m Arrive at 6:37pm in Toronto (YTZ)
CA$827

10:20am - 11:15am
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

5:35pm - 6:37pm
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7706 Depart at 10:20am from Toronto (YTZ) Fly for 0h 55m Arrive at 11:15am in Ottawa (YOW)

Stay in Ottawa for 2 nights

Sun Jun 8th 2025 Air Canada · AC 7711 Depart at 5:35pm from Ottawa (YOW) Fly for 1h 2m Arrive at 6:37pm in Toronto (YTZ)
CA$827

10:20am - 11:15am
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

7:35pm - 8:37pm
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7706 Depart at 10:20am from Toronto (YTZ) Fly for 0h 55m Arrive at 11:15am in Ottawa (YOW)

Stay in Ottawa for 2 nights

Sun Jun 8th 2025 Air Canada · AC 7713 Depart at 7:35pm from Ottawa (YOW) Fly for 1h 2m Arrive at 8:37pm in Toronto (YTZ)
CA$827

8:50am - 9:45am
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

7:35pm - 8:37pm
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7704 Depart at 8:50am from Toronto (YTZ) Fly for 0h 55m Arrive at 9:45am in Ottawa (YOW)

Stay in Ottawa for 2 nights

Sun Jun 8th 2025 Air Canada · AC 7713 Depart at 7:35pm from Ottawa (YOW) Fly for 1h 2m Arrive at 8:37pm in Toronto (YTZ)
CA$827

8:50am - 9:45am
Fri Jun 6th 2025

0h 55m
Toronto (YTZ) → Ottawa (YOW)

Direct

5:35pm - 6:37pm
Sun Jun 8th 2025

1h 2m
Ottawa (YOW) → Toronto (YTZ)

Direct

Fri Jun 6th 2025 Air Canada · AC 7704 Depart at 8:50am from Toronto (YTZ) Fly for 0h 55m Arrive at 9:45am in Ottawa (YOW)

Stay in Ottawa for 2 nights

Sun Jun 8th 2025 Air Canada · AC 7711 Depart at 5:35pm from Ottawa (YOW) Fly for 1h 2m Arrive at 6:37pm in Toronto (YTZ)
CA$1536

12:25pm - 6:10am
Sat Jun 7th 2025

11h 45m
Toronto (YTZ) → Zürich (ZRH)

1 Stop

12:40pm - 5:46pm
Sat Jun 21st 2025

11h 6m
Zürich (ZRH) → Toronto (YTZ)

1 Stop

Sat Jun 7th 2025 Swiss International Air Lines · LX 4862 Depart at 12:25pm from Toronto (YTZ) Fly for 1h 17m Arrive at 1:42pm in Montreal (YUL)

Layover in Montreal for 2h 58m

Sat Jun 7th 2025 Swiss International Air Lines · LX 87 Depart at 4:40pm from Montreal (YUL) Fly for 7h 30m Arrive at 6:10am in Zürich (ZRH)

Stay in Zürich for 13 nights

Sat Jun 21st 2025 Swiss International Air Lines · LX 86 Depart at 12:40pm from Zürich (ZRH) Fly for 8h 20m Arrive at 3:00pm in Montreal (YUL)

Layover in Montreal for 1h 25m

Sat Jun 21st 2025 Swiss International Air Lines · LX 4665 Depart at 4:25pm from Montreal (YUL) Fly for 1h 21m Arrive at 5:46pm in Toronto (YTZ)
CA$1708

12:25pm - 5:10pm
Mon Jun 9th 2025

21h 45m
Toronto (YTZ) → Cairo (CAI)

2 Stops

6:00pm - 5:46pm
Mon Jun 30th 2025

30h 46m
Cairo (CAI) → Toronto (YTZ)

2 Stops

Mon Jun 9th 2025 Swiss International Air Lines · LX 4862 Depart at 12:25pm from Toronto (YTZ) Fly for 1h 17m Arrive at 1:42pm in Montreal (YUL)

Layover in Montreal for 2h 58m

Mon Jun 9th 2025 Swiss International Air Lines · LX 87 Depart at 4:40pm from Montreal (YUL) Fly for 7h 30m Arrive at 6:10am in Zürich (ZRH)

Layover in Zürich for 6h 0m

Tue Jun 10th 2025 Swiss International Air Lines · LX 238 Depart at 12:10pm from Zürich (ZRH) Fly for 4h 0m Arrive at 5:10pm in Cairo (CAI)

Stay in Cairo for 20 nights

Mon Jun 30th 2025 Swiss International Air Lines · LX 239 Depart at 6:00pm from Cairo (CAI) Fly for 4h 20m Arrive at 9:20pm in Zürich (ZRH)

Layover in Zürich for 15h 20m

Tue Jul 1st 2025 Swiss International Air Lines · LX 86 Depart at 12:40pm from Zürich (ZRH) Fly for 8h 20m Arrive at 3:00pm in Montreal (YUL)

Layover in Montreal for 1h 25m

Tue Jul 1st 2025 Swiss International Air Lines · LX 4665 Depart at 4:25pm from Montreal (YUL) Fly for 1h 21m Arrive at 5:46pm in Toronto (YTZ)
CA$1781

12:25pm - 6:10am
Wed Jun 25th 2025

11h 45m
Toronto (YTZ) → Zürich (ZRH)

1 Stop

12:40pm - 5:46pm
Wed Jul 2nd 2025

11h 6m
Zürich (ZRH) → Toronto (YTZ)

1 Stop

Wed Jun 25th 2025 Swiss International Air Lines · LX 4862 Depart at 12:25pm from Toronto (YTZ) Fly for 1h 18m Arrive at 1:43pm in Montreal (YUL)

Layover in Montreal for 2h 57m

Wed Jun 25th 2025 Swiss International Air Lines · LX 87 Depart at 4:40pm from Montreal (YUL) Fly for 7h 30m Arrive at 6:10am in Zürich (ZRH)

Stay in Zürich for 6 nights

Wed Jul 2nd 2025 Swiss International Air Lines · LX 86 Depart at 12:40pm from Zürich (ZRH) Fly for 8h 20m Arrive at 3:00pm in Montreal (YUL)

Layover in Montreal for 1h 25m

Wed Jul 2nd 2025 Swiss International Air Lines · LX 4665 Depart at 4:25pm from Montreal (YUL) Fly for 1h 21m Arrive at 5:46pm in Toronto (YTZ)
CA$2021

12:25pm - 6:10am
Mon Jun 2nd 2025

11h 45m
Toronto (YTZ) → Zürich (ZRH)

1 Stop

12:40pm - 5:50pm
Mon Jun 9th 2025

11h 10m
Zürich (ZRH) → Toronto (YTZ)

1 Stop

Mon Jun 2nd 2025 Swiss International Air Lines · LX 4862 Depart at 12:25pm from Toronto (YTZ) Fly for 1h 17m Arrive at 1:42pm in Montreal (YUL)

Layover in Montreal for 2h 58m

Mon Jun 2nd 2025 Swiss International Air Lines · LX 87 Depart at 4:40pm from Montreal (YUL) Fly for 7h 30m Arrive at 6:10am in Zürich (ZRH)

Stay in Zürich for 6 nights

Mon Jun 9th 2025 Swiss International Air Lines · LX 86 Depart at 12:40pm from Zürich (ZRH) Fly for 8h 20m Arrive at 3:00pm in Montreal (YUL)

Layover in Montreal for 1h 25m

Mon Jun 9th 2025 Swiss International Air Lines · LX 4665 Depart at 4:25pm from Montreal (YUL) Fly for 1h 25m Arrive at 5:50pm in Toronto (YTZ)

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

Andy Travels

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Flights from Toronto (YTZ)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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