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Find cheap airline tickets from Boston to Chicago by date

Departure: Return: Sorted by:

$99

outward: Dec 13, 2023
2:33p BOS » 12:41a MDW
Frontier Airlines 1 stop (10h08m)

inbound: Dec 18, 2023
12:22a MDW » 2:46p BOS
Frontier Airlines 1 stop (14h24m)

$132

outward: Dec 13, 2023
2:33p BOS » 12:41a MDW
Frontier Airlines 1 stop (10h08m)

inbound: Dec 17, 2023
3:25a ORD » 2:11p BOS
Frontier Airlines 1 stop (10h46m)

$158

outward: Dec 15, 2023
3:37a BOS » 5:50p ORD
Spirit Airlines 1 stop (14h13m)

inbound: Dec 17, 2023
2:40p ORD » 5:22p BOS
Spirit Airlines 1 stop (26h42m)

$159

outward: Dec 13, 2023
2:33p BOS » 12:41a MDW
Frontier Airlines 1 stop (10h08m)

inbound: Dec 17, 2023
3:25a ORD » 2:11p BOS
Frontier Airlines 1 stop (10h46m)

$191

outward: Dec 15, 2023
12:55a BOS » 4:15p ORD
Unknown Company 1 stop (15h20m)

inbound: Dec 16, 2023
2:04p ORD » 4:23p BOS
American Airlines direct (2h19m)

$308

outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)

inbound: May 27, 2024
11:06p ORD » 4:00a BOS
JetBlue 1 stop (4h54m)

$308

outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)

inbound: May 27, 2024
11:06p ORD » 4:00a BOS
JetBlue 1 stop (4h54m)

$321

outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)

inbound: May 28, 2024
1:46a ORD » 4:20a BOS
JetBlue direct (2h34m)

$321

outward: May 24, 2024
10:06p BOS » 1:11a ORD
JetBlue direct (3h05m)

inbound: May 28, 2024
1:46a ORD » 4:20a BOS
JetBlue direct (2h34m)

$388

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$390

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$391

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$393

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$396

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$396

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$396

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$398

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$407

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$407

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$407

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$407

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$408

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$408

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$408

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$408

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$408

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$409

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$410

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$410

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

$410

outward: May 24, 2024
5:30p BOS » 2:03a ORD
Sun Country 1 stop (8h33m)

inbound: May 28, 2024
3:00a ORD » 4:33p BOS
Sun Country 1 stop (13h33m)

Return

Departure

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

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

Airlines operating flights from Boston to Chicago

Departure: Airline

Delta Air Lines

outbound: Dec 13, 2023
Delta Air Lines direct

return: Dec 16, 2023
Delta Air Lines direct

United Airlines

outbound: Dec 13, 2023
United Airlines direct

return: Dec 16, 2023
United Airlines direct

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

Travel tips for flights Boston - Chicago

Average flight duration: 2h19m (direct flight)

Arrival city:
Chicago, USA
Airport(s):
Chicago Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Dec 7, 2023 8:46 PM, GMT-6
Weather:
min. 37ºF, max. 53ºF

Departure city:
Boston, USA
Airport(s):
Boston Logan International Airport (BOS)
Manchester–Boston Regional Airport (MHT)
Local time:
Dec 7, 2023 9:46 PM, GMT-5
Weather:
min. 28ºF, max. 45ºF

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