Flights from Chicago to Boston (ORD to BOS)

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

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US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

11:01am - 1:03pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 1823 Depart at 11:01am from Boston (BOS) Fly for 3h 2m Arrive at 1:03pm in Chicago (ORD)
US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Thu Mar 27th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

12:18pm - 2:20pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 1732 Depart at 12:18pm from Boston (BOS) Fly for 3h 2m Arrive at 2:20pm in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

11:01am - 1:03pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1823 Depart at 11:01am from Boston (BOS) Fly for 3h 2m Arrive at 1:03pm in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Thu Mar 27th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

12:18pm - 2:20pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1732 Depart at 12:18pm from Boston (BOS) Fly for 3h 2m Arrive at 2:20pm in Chicago (ORD)
US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:25am - 9:29am
Thu Mar 27th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 1316 Depart at 7:25am from Boston (BOS) Fly for 3h 4m Arrive at 9:29am in Chicago (ORD)
US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Thu Mar 27th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1209

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:20am - 9:24am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1316 Depart at 7:20am from Boston (BOS) Fly for 3h 4m Arrive at 9:24am in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Thu Mar 27th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:25am - 9:29am
Thu Mar 27th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 1316 Depart at 7:25am from Boston (BOS) Fly for 3h 4m Arrive at 9:29am in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1209

4:00pm - 7:20pm
Tue Mar 25th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:20am - 9:24am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1316 Depart at 7:20am from Boston (BOS) Fly for 3h 4m Arrive at 9:24am in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Thu Mar 27th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

11:01am - 1:03pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1823 Depart at 11:01am from Boston (BOS) Fly for 3h 2m Arrive at 1:03pm in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

12:18pm - 2:20pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1732 Depart at 12:18pm from Boston (BOS) Fly for 3h 2m Arrive at 2:20pm in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

7:25am - 9:29am
Thu Mar 27th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 1316 Depart at 7:25am from Boston (BOS) Fly for 3h 4m Arrive at 9:29am in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Thu Mar 27th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

7:20am - 9:24am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1316 Depart at 7:20am from Boston (BOS) Fly for 3h 4m Arrive at 9:24am in Chicago (ORD)
US$1209

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1446

7:30am - 10:49am
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 2 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1446

11:15am - 2:34pm
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 2 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1446

4:05pm - 7:25pm
Wed Mar 26th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 450 Depart at 4:05pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:25pm in Boston (BOS)

Stay in Boston for 2 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1446

2:15pm - 5:37pm
Wed Mar 26th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 580 Depart at 2:15pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:37pm in Boston (BOS)

Stay in Boston for 2 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1446

9:20am - 12:43pm
Wed Mar 26th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 2 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1446

6:13pm - 9:37pm
Wed Mar 26th 2025

2h 24m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1989 Depart at 6:13pm from Chicago (ORD) Fly for 2h 24m Arrive at 9:37pm in Boston (BOS)

Stay in Boston for 2 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1448

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

11:01am - 1:03pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 1823 Depart at 11:01am from Boston (BOS) Fly for 3h 2m Arrive at 1:03pm in Chicago (ORD)
US$1448

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1448

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

12:18pm - 2:20pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 1732 Depart at 12:18pm from Boston (BOS) Fly for 3h 2m Arrive at 2:20pm in Chicago (ORD)
US$1448

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:20am - 9:24am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 1316 Depart at 7:20am from Boston (BOS) Fly for 3h 4m Arrive at 9:24am in Chicago (ORD)
US$1448

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Wed Mar 26th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

11:15am - 2:34pm
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Thu Mar 27th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 1 night

Thu Mar 27th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1449

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

4:30pm - 6:32pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 1 night

Wed Mar 26th 2025 United Airlines · UA 2040 Depart at 4:30pm from Boston (BOS) Fly for 3h 2m Arrive at 6:32pm in Chicago (ORD)
US$1449

11:15am - 2:34pm
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1449

11:15am - 2:34pm
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

11:01am - 1:03pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1823 Depart at 11:01am from Boston (BOS) Fly for 3h 2m Arrive at 1:03pm in Chicago (ORD)
US$1449

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

11:01am - 1:03pm
Thu Mar 27th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 2 nights

Thu Mar 27th 2025 United Airlines · UA 1823 Depart at 11:01am from Boston (BOS) Fly for 3h 2m Arrive at 1:03pm in Chicago (ORD)
US$1449

11:15am - 2:34pm
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

12:18pm - 2:20pm
Wed Mar 26th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 0 nights

Wed Mar 26th 2025 United Airlines · UA 1732 Depart at 12:18pm from Boston (BOS) Fly for 3h 2m Arrive at 2:20pm in Chicago (ORD)
US$1449

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

12:18pm - 2:20pm
Tue Mar 25th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 0 nights

Tue Mar 25th 2025 United Airlines · UA 1732 Depart at 12:18pm from Boston (BOS) Fly for 3h 2m Arrive at 2:20pm in Chicago (ORD)
US$1449

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

11:01am - 1:03pm
Tue Mar 25th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 0 nights

Tue Mar 25th 2025 United Airlines · UA 1823 Depart at 11:01am from Boston (BOS) Fly for 3h 2m Arrive at 1:03pm in Chicago (ORD)
US$1449

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

4:30pm - 6:32pm
Tue Mar 25th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 0 nights

Tue Mar 25th 2025 United Airlines · UA 2040 Depart at 4:30pm from Boston (BOS) Fly for 3h 2m Arrive at 6:32pm in Chicago (ORD)
US$1449

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Tue Mar 25th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 0 nights

Tue Mar 25th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1449

7:30am - 10:49am
Fri Mar 28th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 0 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

11:15am - 2:34pm
Fri Mar 28th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 0 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 3 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Fri Mar 28th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 2 nights

Fri Mar 28th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

9:30pm - 12:50am
Fri Mar 28th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 0 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

4:00pm - 7:20pm
Fri Mar 28th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 0 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Tue Mar 25th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 0 nights

Tue Mar 25th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:25am - 9:29am
Tue Mar 25th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 0 nights

Tue Mar 25th 2025 United Airlines · UA 1316 Depart at 7:25am from Boston (BOS) Fly for 3h 4m Arrive at 9:29am in Chicago (ORD)
US$1449

1:55pm - 5:17pm
Fri Mar 28th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 580 Depart at 1:55pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:17pm in Boston (BOS)

Stay in Boston for 0 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

9:20am - 12:43pm
Tue Mar 25th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 3 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1449

6:13pm - 9:37pm
Fri Mar 28th 2025

2h 24m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 1989 Depart at 6:13pm from Chicago (ORD) Fly for 2h 24m Arrive at 9:37pm in Boston (BOS)

Stay in Boston for 0 nights

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1610

7:30am - 10:49am
Thu Mar 27th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

7:30am - 10:49am
Thu Mar 27th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

11:15am - 2:34pm
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

11:15am - 2:34pm
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

4:05pm - 7:25pm
Wed Mar 26th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 450 Depart at 4:05pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:25pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

4:05pm - 7:25pm
Wed Mar 26th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 450 Depart at 4:05pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:25pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

9:30pm - 12:50am
Thu Mar 27th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

9:30pm - 12:50am
Thu Mar 27th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

2:15pm - 5:37pm
Wed Mar 26th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 580 Depart at 2:15pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:37pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

2:15pm - 5:37pm
Wed Mar 26th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 580 Depart at 2:15pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:37pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

1:55pm - 5:17pm
Thu Mar 27th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 580 Depart at 1:55pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:17pm in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

1:55pm - 5:17pm
Thu Mar 27th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

9:30am - 11:27am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 580 Depart at 1:55pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:17pm in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 378 Depart at 9:30am from Boston (BOS) Fly for 2h 57m Arrive at 11:27am in Chicago (ORD)
US$1610

1:55pm - 5:17pm
Thu Mar 27th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 580 Depart at 1:55pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:17pm in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

9:20am - 12:43pm
Wed Mar 26th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

9:20am - 12:43pm
Wed Mar 26th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

9:20am - 12:43pm
Thu Mar 27th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

9:20am - 12:43pm
Thu Mar 27th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 3 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1610

6:13pm - 9:37pm
Wed Mar 26th 2025

2h 24m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1989 Depart at 6:13pm from Chicago (ORD) Fly for 2h 24m Arrive at 9:37pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1610

6:13pm - 9:37pm
Wed Mar 26th 2025

2h 24m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1989 Depart at 6:13pm from Chicago (ORD) Fly for 2h 24m Arrive at 9:37pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1619

7:30am - 10:49am
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1619

7:30am - 10:49am
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1619

7:30am - 10:49am
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

9:30am - 11:27am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 378 Depart at 9:30am from Boston (BOS) Fly for 2h 57m Arrive at 11:27am in Chicago (ORD)
US$1619

11:15am - 2:34pm
Wed Mar 26th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

9:30am - 11:27am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 378 Depart at 9:30am from Boston (BOS) Fly for 2h 57m Arrive at 11:27am in Chicago (ORD)
US$1619

4:05pm - 7:25pm
Wed Mar 26th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

9:30am - 11:27am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 450 Depart at 4:05pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:25pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 378 Depart at 9:30am from Boston (BOS) Fly for 2h 57m Arrive at 11:27am in Chicago (ORD)
US$1619

2:15pm - 5:37pm
Wed Mar 26th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

9:30am - 11:27am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 580 Depart at 2:15pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:37pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 378 Depart at 9:30am from Boston (BOS) Fly for 2h 57m Arrive at 11:27am in Chicago (ORD)
US$1619

9:20am - 12:43pm
Wed Mar 26th 2025

2h 23m
Chicago (ORD) → Boston (BOS)

Direct

9:30am - 11:27am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 2201 Depart at 9:20am from Chicago (ORD) Fly for 2h 23m Arrive at 12:43pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 378 Depart at 9:30am from Boston (BOS) Fly for 2h 57m Arrive at 11:27am in Chicago (ORD)
US$1619

6:13pm - 9:37pm
Wed Mar 26th 2025

2h 24m
Chicago (ORD) → Boston (BOS)

Direct

9:30am - 11:27am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Wed Mar 26th 2025 United Airlines · UA 1989 Depart at 6:13pm from Chicago (ORD) Fly for 2h 24m Arrive at 9:37pm in Boston (BOS)

Stay in Boston for 4 nights

Mon Mar 31st 2025 United Airlines · UA 378 Depart at 9:30am from Boston (BOS) Fly for 2h 57m Arrive at 11:27am in Chicago (ORD)
US$1624

11:15am - 2:34pm
Fri Mar 28th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1624

7:30am - 10:49am
Fri Mar 28th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1624

11:15am - 2:34pm
Fri Mar 28th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 307 Depart at 11:15am from Chicago (ORD) Fly for 2h 19m Arrive at 2:34pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1624

7:30am - 10:49am
Fri Mar 28th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1624

9:30pm - 12:50am
Fri Mar 28th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1624

9:30pm - 12:50am
Fri Mar 28th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1624

4:00pm - 7:20pm
Fri Mar 28th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1624

4:00pm - 7:20pm
Fri Mar 28th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 450 Depart at 4:00pm from Chicago (ORD) Fly for 2h 20m Arrive at 7:20pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1624

1:55pm - 5:17pm
Fri Mar 28th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 580 Depart at 1:55pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:17pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1624

1:55pm - 5:17pm
Fri Mar 28th 2025

2h 22m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 580 Depart at 1:55pm from Chicago (ORD) Fly for 2h 22m Arrive at 5:17pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1624

6:13pm - 9:37pm
Fri Mar 28th 2025

2h 24m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 1989 Depart at 6:13pm from Chicago (ORD) Fly for 2h 24m Arrive at 9:37pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am in Chicago (ORD)
US$1624

6:13pm - 9:37pm
Fri Mar 28th 2025

2h 24m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 7:57am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Fri Mar 28th 2025 United Airlines · UA 1989 Depart at 6:13pm from Chicago (ORD) Fly for 2h 24m Arrive at 9:37pm in Boston (BOS)

Stay in Boston for 2 nights

Mon Mar 31st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)
US$1624

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

9:20am - 11:22am
Thu Mar 27th 2025

3h 2m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 2 nights

Thu Mar 27th 2025 United Airlines · UA 316 Depart at 9:20am from Boston (BOS) Fly for 3h 2m Arrive at 11:22am in Chicago (ORD)
US$1624

7:30am - 10:49am
Thu Mar 27th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 1 night

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1624

9:30pm - 12:50am
Thu Mar 27th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

6:00am - 8:04am
Sat Mar 29th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Thu Mar 27th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 1 night

Sat Mar 29th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 3h 4m Arrive at 8:04am in Chicago (ORD)
US$1624

9:30pm - 12:50am
Mon Mar 24th 2025

2h 20m
Chicago (ORD) → Boston (BOS)

Direct

7:25am - 9:29am
Thu Mar 27th 2025

3h 4m
Boston (BOS) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1495 Depart at 9:30pm from Chicago (ORD) Fly for 2h 20m Arrive at 12:50am in Boston (BOS)

Stay in Boston for 2 nights

Thu Mar 27th 2025 United Airlines · UA 1316 Depart at 7:25am from Boston (BOS) Fly for 3h 4m Arrive at 9:29am in Chicago (ORD)
US$1629

7:30am - 10:49am
Tue Mar 25th 2025

2h 19m
Chicago (ORD) → Boston (BOS)

Direct

7:43am - 9:40am
Mon Mar 31st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

Tue Mar 25th 2025 United Airlines · UA 2067 Depart at 7:30am from Chicago (ORD) Fly for 2h 19m Arrive at 10:49am in Boston (BOS)

Stay in Boston for 5 nights

Mon Mar 31st 2025 United Airlines · UA 2251 Depart at 7:43am from Boston (BOS) Fly for 2h 57m Arrive at 9:40am 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 Boston (ORD to BOS)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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