Flights from Chicago to Portland (ORD to PDX)

Discover more affordable routes and cheaper dates from Chicago to Portland (ORD to PDX) within a date range.

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US$1760

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

6:00am - 2:16pm
Thu Mar 27th 2025

6h 16m
Portland (PDX) → Chicago (ORD)

1 Stop

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 1 night

Thu Mar 27th 2025 Hawaiian Airlines · HA 6394 Depart at 6:00am from Portland (PDX) Fly for 0h 59m Arrive at 6:59am in Seattle (SEA)

Layover in Seattle for 0h 56m

Thu Mar 27th 2025 Hawaiian Airlines · HA 6671 Depart at 7:55am from Seattle (SEA) Fly for 4h 21m Arrive at 2:16pm in Chicago (ORD)
US$1860

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

4:00pm - 11:59pm
Mon Mar 31st 2025

5h 59m
Portland (PDX) → Chicago (ORD)

1 Stop

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 5 nights

Mon Mar 31st 2025 Hawaiian Airlines · HA 6401 Depart at 4:00pm from Portland (PDX) Fly for 0h 53m Arrive at 4:53pm in Seattle (SEA)

Layover in Seattle for 1h 9m

Mon Mar 31st 2025 Hawaiian Airlines · HA 6819 Depart at 6:02pm from Seattle (SEA) Fly for 3h 57m Arrive at 11:59pm in Chicago (ORD)
US$2035

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Wed Mar 26th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 0 nights

Wed Mar 26th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2205

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sat Mar 29th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 3 nights

Sat Mar 29th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2249

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Wed Mar 26th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 1 night

Wed Mar 26th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2324

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Thu Mar 27th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 1 night

Thu Mar 27th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2324

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Mon Mar 31st 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 5 nights

Mon Mar 31st 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2333

4:15pm - 6:48pm
Wed Mar 26th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 0 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2333

8:16pm - 10:56pm
Tue Mar 25th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 426 Depart at 8:16pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:56pm in Portland (PDX)

Stay in Portland for 6 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2333

9:11am - 11:54am
Wed Mar 26th 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 0 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2373

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Fri Mar 28th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 2 nights

Fri Mar 28th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2385

12:45pm - 3:15pm
Mon Mar 31st 2025

4h 30m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 31st 2025 United Airlines · UA 2673 Depart at 12:45pm from Chicago (ORD) Fly for 4h 30m Arrive at 3:15pm in Portland (PDX)

Stay in Portland for 0 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2386

4:12pm - 6:45pm
Mon Mar 31st 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 31st 2025 United Airlines · UA 1965 Depart at 4:12pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:45pm in Portland (PDX)

Stay in Portland for 0 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2386

9:15am - 11:50am
Mon Mar 31st 2025

4h 35m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 31st 2025 United Airlines · UA 1994 Depart at 9:15am from Chicago (ORD) Fly for 4h 35m Arrive at 11:50am in Portland (PDX)

Stay in Portland for 0 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2386

8:20pm - 10:57pm
Sun Mar 30th 2025

4h 37m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 30th 2025 United Airlines · UA 426 Depart at 8:20pm from Chicago (ORD) Fly for 4h 37m Arrive at 10:57pm in Portland (PDX)

Stay in Portland for 1 night

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2432

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Fri Mar 28th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Alaska Airlines · AS 325 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 2 nights

Fri Mar 28th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2490

3:16pm - 5:50pm
Sun Mar 23rd 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Mon Mar 24th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 0 nights

Mon Mar 24th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2493

4:15pm - 6:48pm
Thu Mar 27th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2493

7:59pm - 10:39pm
Thu Mar 27th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2498

4:12pm - 6:45pm
Sun Mar 30th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 30th 2025 United Airlines · UA 1965 Depart at 4:12pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:45pm in Portland (PDX)

Stay in Portland for 1 night

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2498

8:05pm - 10:45pm
Fri Mar 28th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 426 Depart at 8:05pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:45pm in Portland (PDX)

Stay in Portland for 3 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2517

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Mon Mar 31st 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 6 nights

Mon Mar 31st 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2537

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Thu Mar 27th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 2 nights

Thu Mar 27th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2537

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sat Mar 29th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 4 nights

Sat Mar 29th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2540

4:15pm - 6:48pm
Tue Mar 25th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 0 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2540

9:11am - 11:54am
Tue Mar 25th 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 0 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2572

7:59pm - 10:39pm
Sun Mar 23rd 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 3 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2572

7:59pm - 10:39pm
Sun Mar 23rd 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 2 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2573

4:15pm - 6:48pm
Mon Mar 24th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 2 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2573

7:59pm - 10:39pm
Mon Mar 24th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 2 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2587

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Fri Mar 28th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 3 nights

Fri Mar 28th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2598

3:16pm - 5:50pm
Sun Mar 23rd 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Wed Mar 26th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Alaska Airlines · AS 325 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 2 nights

Wed Mar 26th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2642

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sun Mar 30th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 4 nights

Sun Mar 30th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2705

4:15pm - 6:48pm
Tue Mar 25th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 6 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2705

9:11am - 11:54am
Tue Mar 25th 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 6 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2713

4:15pm - 6:48pm
Mon Mar 24th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 7 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2713

7:59pm - 10:39pm
Mon Mar 24th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 7 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2737

7:59pm - 10:39pm
Sat Mar 22nd 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 9 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2737

7:59pm - 10:39pm
Wed Mar 26th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 5 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2737

7:59pm - 10:39pm
Sat Mar 29th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 29th 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 2 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2737

9:11am - 11:54am
Wed Mar 26th 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 5 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2738

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Wed Mar 26th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 3 nights

Wed Mar 26th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2760

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Mon Mar 24th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 1 night

Mon Mar 24th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2761

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Thu Mar 27th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 4 nights

Thu Mar 27th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2766

3:16pm - 5:50pm
Thu Mar 27th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Mon Mar 31st 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Thu Mar 27th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 3 nights

Mon Mar 31st 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2775

3:16pm - 5:50pm
Sun Mar 23rd 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Tue Mar 25th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 1 night

Tue Mar 25th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2775

3:16pm - 5:50pm
Wed Mar 26th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sat Mar 29th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Wed Mar 26th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 2 nights

Sat Mar 29th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2775

3:16pm - 5:50pm
Sun Mar 23rd 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Thu Mar 27th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 3 nights

Thu Mar 27th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2775

3:16pm - 5:50pm
Thu Mar 27th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sat Mar 29th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Thu Mar 27th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 1 night

Sat Mar 29th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2777

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 0 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2833

4:15pm - 6:48pm
Sun Mar 23rd 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 3 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2833

4:15pm - 6:48pm
Sun Mar 23rd 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 2 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2833

7:59pm - 10:39pm
Sat Mar 22nd 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 3 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2833

7:59pm - 10:39pm
Sat Mar 22nd 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 4 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2833

9:11am - 11:54am
Sun Mar 23rd 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 3 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2849

3:16pm - 5:50pm
Wed Mar 26th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Mon Mar 31st 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Wed Mar 26th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 4 nights

Mon Mar 31st 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2849

3:16pm - 5:50pm
Sun Mar 23rd 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sat Mar 29th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 5 nights

Sat Mar 29th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2870

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Thu Mar 27th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Alaska Airlines · AS 413 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 4 nights

Thu Mar 27th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2870

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Wed Mar 26th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Alaska Airlines · AS 413 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 3 nights

Wed Mar 26th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2884

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Fri Mar 28th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2884

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 6 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2884

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Sun Mar 30th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 5 nights

Sun Mar 30th 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2884

3:16pm - 5:50pm
Tue Mar 25th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

2:02pm - 8:08pm
Mon Mar 31st 2025

4h 6m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 5 nights

Mon Mar 31st 2025 United Airlines · UA 2360 Depart at 2:02pm from Portland (PDX) Fly for 4h 6m Arrive at 8:08pm in Chicago (ORD)
US$2885

3:16pm - 5:50pm
Thu Mar 27th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Fri Mar 28th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Thu Mar 27th 2025 Alaska Airlines · AS 325 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 0 nights

Fri Mar 28th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$2945

4:15pm - 6:48pm
Wed Mar 26th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 5 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2945

7:59pm - 10:39pm
Sun Mar 23rd 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:00pm
Wed Mar 26th 2025

4h 0m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 2 nights

Wed Mar 26th 2025 United Airlines · UA 1693 Depart at 7:00am from Portland (PDX) Fly for 4h 0m Arrive at 1:00pm in Chicago (ORD)
US$2945

7:59pm - 10:39pm
Sun Mar 23rd 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:00pm
Tue Mar 25th 2025

4h 0m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 426 Depart at 7:59pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:39pm in Portland (PDX)

Stay in Portland for 1 night

Tue Mar 25th 2025 United Airlines · UA 1693 Depart at 7:00am from Portland (PDX) Fly for 4h 0m Arrive at 1:00pm in Chicago (ORD)
US$2971

9:11am - 11:54am
Mon Mar 24th 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 7 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2977

4:15pm - 6:48pm
Mon Mar 24th 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Mon Mar 24th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 0 nights

Mon Mar 24th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$2990

9:11am - 11:54am
Thu Mar 27th 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$2998

12:45pm - 3:15pm
Sun Mar 30th 2025

4h 30m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 30th 2025 United Airlines · UA 2673 Depart at 12:45pm from Chicago (ORD) Fly for 4h 30m Arrive at 3:15pm in Portland (PDX)

Stay in Portland for 1 night

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$3047

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Fri Mar 28th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 5 nights

Fri Mar 28th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$3047

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Mon Mar 31st 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 8 nights

Mon Mar 31st 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$3047

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sat Mar 29th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 6 nights

Sat Mar 29th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$3061

8:16pm - 10:56pm
Tue Mar 25th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Sat Mar 29th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 426 Depart at 8:16pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:56pm in Portland (PDX)

Stay in Portland for 4 nights

Sat Mar 29th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3073

4:15pm - 6:48pm
Sat Mar 22nd 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 4 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3073

4:15pm - 6:48pm
Sat Mar 22nd 2025

4h 33m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 1616 Depart at 4:15pm from Chicago (ORD) Fly for 4h 33m Arrive at 6:48pm in Portland (PDX)

Stay in Portland for 3 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3073

8:16pm - 10:56pm
Tue Mar 25th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Fri Mar 28th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 426 Depart at 8:16pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:56pm in Portland (PDX)

Stay in Portland for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3073

8:16pm - 10:56pm
Tue Mar 25th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Sun Mar 30th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 426 Depart at 8:16pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:56pm in Portland (PDX)

Stay in Portland for 5 nights

Sun Mar 30th 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$3073

9:11am - 11:54am
Sun Mar 23rd 2025

4h 43m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Tue Mar 25th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1044 Depart at 9:11am from Chicago (ORD) Fly for 4h 43m Arrive at 11:54am in Portland (PDX)

Stay in Portland for 2 nights

Tue Mar 25th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3073

8:16pm - 10:56pm
Tue Mar 25th 2025

4h 40m
Chicago (ORD) → Portland (PDX)

Direct

2:02pm - 8:08pm
Mon Mar 31st 2025

4h 6m
Portland (PDX) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 426 Depart at 8:16pm from Chicago (ORD) Fly for 4h 40m Arrive at 10:56pm in Portland (PDX)

Stay in Portland for 5 nights

Mon Mar 31st 2025 United Airlines · UA 2360 Depart at 2:02pm from Portland (PDX) Fly for 4h 6m Arrive at 8:08pm in Chicago (ORD)
US$3079

3:16pm - 5:50pm
Sun Mar 23rd 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Sun Mar 30th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 6 nights

Sun Mar 30th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$3097

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Sat Mar 29th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 5 nights

Sat Mar 29th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3097

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Sun Mar 30th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 6 nights

Sun Mar 30th 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$3097

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 7 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$3097

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Mon Mar 24th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 0 nights

Mon Mar 24th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3097

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Fri Mar 28th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3097

3:16pm - 5:50pm
Mon Mar 24th 2025

4h 34m
Chicago (ORD) → Portland (PDX)

Direct

2:02pm - 8:08pm
Mon Mar 31st 2025

4h 6m
Portland (PDX) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Hawaiian Airlines · HA 6293 Depart at 3:16pm from Chicago (ORD) Fly for 4h 34m Arrive at 5:50pm in Portland (PDX)

Stay in Portland for 6 nights

Mon Mar 31st 2025 United Airlines · UA 2360 Depart at 2:02pm from Portland (PDX) Fly for 4h 6m Arrive at 8:08pm in Chicago (ORD)
US$3122

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Tue Mar 25th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 2 nights

Tue Mar 25th 2025 Hawaiian Airlines · HA 6373 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$3126

8:20pm - 10:57pm
Sun Mar 30th 2025

4h 37m
Chicago (ORD) → Portland (PDX)

Direct

2:02pm - 8:08pm
Mon Mar 31st 2025

4h 6m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 30th 2025 United Airlines · UA 426 Depart at 8:20pm from Chicago (ORD) Fly for 4h 37m Arrive at 10:57pm in Portland (PDX)

Stay in Portland for 0 nights

Mon Mar 31st 2025 United Airlines · UA 2360 Depart at 2:02pm from Portland (PDX) Fly for 4h 6m Arrive at 8:08pm in Chicago (ORD)
US$3157

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Tue Mar 25th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Alaska Airlines · AS 413 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 2 nights

Tue Mar 25th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$3157

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

7:00am - 1:05pm
Fri Mar 28th 2025

4h 5m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Alaska Airlines · AS 413 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 5 nights

Fri Mar 28th 2025 Alaska Airlines · AS 327 Depart at 7:00am from Portland (PDX) Fly for 4h 5m Arrive at 1:05pm in Chicago (ORD)
US$3609

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Thu Mar 27th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 5 nights

Thu Mar 27th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3609

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Sat Mar 22nd 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 0 nights

Sat Mar 22nd 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3609

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

11:00am - 4:57pm
Thu Mar 27th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 4 nights

Thu Mar 27th 2025 United Airlines · UA 1335 Depart at 11:00am from Portland (PDX) Fly for 3h 57m Arrive at 4:57pm in Chicago (ORD)
US$3609

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Fri Mar 28th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 6 nights

Fri Mar 28th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3609

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Sat Mar 29th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 7 nights

Sat Mar 29th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)
US$3664

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Mon Mar 31st 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Alaska Airlines · AS 413 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 9 nights

Mon Mar 31st 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$3738

12:45pm - 3:15pm
Sun Mar 30th 2025

4h 30m
Chicago (ORD) → Portland (PDX)

Direct

11:59pm - 5:56am
Sun Mar 30th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sun Mar 30th 2025 United Airlines · UA 2673 Depart at 12:45pm from Chicago (ORD) Fly for 4h 30m Arrive at 3:15pm in Portland (PDX)

Stay in Portland for 0 nights

Sun Mar 30th 2025 United Airlines · UA 1490 Depart at 11:59pm from Portland (PDX) Fly for 3h 57m Arrive at 5:56am in Chicago (ORD)
US$4179

2:04pm - 4:36pm
Sat Mar 22nd 2025

4h 32m
Chicago (ORD) → Portland (PDX)

Direct

11:58pm - 5:55am
Wed Mar 26th 2025

3h 57m
Portland (PDX) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Hawaiian Airlines · HA 6293 Depart at 2:04pm from Chicago (ORD) Fly for 4h 32m Arrive at 4:36pm in Portland (PDX)

Stay in Portland for 4 nights

Wed Mar 26th 2025 United Airlines · UA 2384 Depart at 11:58pm from Portland (PDX) Fly for 3h 57m Arrive at 5:55am in Chicago (ORD)

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

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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 Chicago to Portland (ORD to PDX)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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