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Find cheap airline tickets from Chicago to Boston by date

Departure: Return: Sorted by:

$227

outward: May 29, 2022
4:39a ORD » 7:00a BOS
United Airlines direct (2h21m)

inbound: May 30, 2022
5:31p BOS » 3:34p MDW
Frontier Airlines 1 stop (22h03m)

$252

outward: May 29, 2022
1:10a MDW » 6:51a BOS
Delta Air Lines 1 stop (5h41m)

inbound: Jun 1, 2022
3:59a BOS » 2:47p ORD
Delta Air Lines 1 stop (10h48m)

$255

outward: May 29, 2022
4:39a ORD » 7:00a BOS
United Airlines direct (2h21m)

inbound: Jun 1, 2022
1:25a BOS » 5:39p MDW
Unknown Company 1 stop (16h14m)

$295

outward: May 29, 2022
4:39a ORD » 7:00a BOS
United Airlines direct (2h21m)

inbound: May 30, 2022
12:15p BOS » 1:30p ORD
Unknown Company 1 stop (25h15m)

$307

outward: Jul 19, 2022
3:15a ORD » 5:47a BOS
Delta Air Lines direct (2h32m)

inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)

$310

outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)

inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)

$328

outward: Jul 18, 2022
6:05p ORD » 1:46a BOS
Spirit Airlines 1 stop (7h41m)

inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)

$333

outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$333

outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$338

outward: Jul 7, 2022
6:05p ORD » 1:46a BOS
Spirit Airlines 1 stop (7h41m)

inbound: Jul 10, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)

$340

outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)

inbound: Jul 21, 2022
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)

$340

outward: Jul 19, 2022
4:08a ORD » 6:30a BOS
United Airlines direct (2h22m)

inbound: Jul 21, 2022
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)

$341

outward: Jul 18, 2022
6:05p ORD » 1:46a BOS
Spirit Airlines 1 stop (7h41m)

inbound: Jul 21, 2022
5:13p BOS » 11:40p ORD
Spirit Airlines 1 stop (6h27m)

$358

outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)

inbound: Jul 21, 2022
11:30a BOS » 2:22p ORD
American Airlines direct (2h52m)

$359

outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)

inbound: Jul 21, 2022
6:33p BOS » 9:24p ORD
American Airlines direct (2h51m)

$361

outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$361

outward: May 27, 2022
12:15p ORD » 11:24p BOS
Spirit Airlines 1 stop (11h09m)

inbound: May 31, 2022
2:30p BOS » 10:07p ORD
Spirit Airlines 1 stop (7h37m)

$364

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$367

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
4:55p BOS » 1:32a MDW
Unknown Company 1 stop (8h37m)

$367

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
4:55p BOS » 1:32a MDW
Unknown Company 1 stop (8h37m)

$367

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
4:55p BOS » 1:32a MDW
Unknown Company 1 stop (8h37m)

$382

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$382

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$383

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$383

outward: Jul 19, 2022
2:45a ORD » 5:11a BOS
JetBlue direct (2h26m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$390

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$391

outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$396

outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

$398

outward: Jul 18, 2022
2:16p MDW » 8:44p BOS
Allegiant Air 1 stop (6h28m)

inbound: Jul 21, 2022
12:15p BOS » 3:11p ORD
JetBlue direct (2h56m)

$399

outward: Jul 19, 2022
3:05a ORD » 5:37a BOS
Delta Air Lines direct (2h32m)

inbound: Jul 21, 2022
12:45p BOS » 3:43p ORD
Delta Air Lines direct (2h58m)

Return

Departure

Choose when you'd like to depart to Boston (USA):

Find the cheapest Chicago Boston flight by browsing the dates below to find alternative flight prices found in the last days. To launch a flight search for Chicago - Boston with these new dates, click on an offer. Want to depart from another city? Choose:

Airlines operating flights from Chicago to Boston

Departure: Airline

Spirit Airlines

outbound: May 28, 2022
Spirit Airlines 1 stop

return: May 31, 2022
Spirit Airlines 1 stop

United Airlines

outbound: May 27, 2022
United Airlines direct

return: May 31, 2022
JetBlue 1 stop

American Airlines

outbound: Jul 7, 2022
American Airlines 1 stop

return: Jul 10, 2022
Spirit Airlines 1 stop

Airline tickets Chicago - Boston found in the last 30 days.

Travel tips for flights Chicago - Boston

Average flight duration: 2h21m (direct flight)

Arrival city:
Boston, USA
Airport(s):
Boston Logan International Airport (BOS)
Manchester–Boston Regional Airport (MHT)
Local time:
May 22, 2022 10:21 AM, GMT-4
Weather:
min. 63ºF, max. 84ºF

Departure city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
May 22, 2022 9:21 AM, GMT-5
Weather:
min. 50ºF, max. 59ºF

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