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Find cheap airline tickets from Boston to Chicago by date

Departure: Return: Sorted by:

$112

outward: Feb 26, 2020
8:26p BOS » 11:28p ORD
JetBlue direct (3h02m)

inbound: Mar 11, 2020
3:05p ORD » 5:25p BOS
JetBlue direct (2h20m)

$112

outward: Feb 27, 2020
12:39p BOS » 3:41p ORD
JetBlue direct (3h02m)

inbound: Mar 5, 2020
12:57p ORD » 3:12p BOS
JetBlue direct (2h15m)

$135

outward: Mar 2, 2020
6:10p BOS » 9:15p ORD
Delta Air Lines direct (3h05m)

inbound: Mar 9, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)

$139

outward: Apr 16, 2020
11:30a BOS » 2:10p MDW
Southwest Airlines direct (2h40m)

inbound: Apr 23, 2020
1:05p MDW » 3:20p BOS
Southwest Airlines direct (2h15m)

$140

outward: Mar 19, 2020
1:27p BOS » 4:31p ORD
JetBlue direct (3h04m)

inbound: Mar 26, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)

$145

outward: May 11, 2020
9:23p BOS » 12:07a ORD
Spirit Airlines direct (2h44m)

inbound: May 19, 2020
4:49a ORD » 4:52p BOS
Spirit Airlines 1 stop (12h03m)

$149

outward: Jun 13, 2020
12:28p BOS » 3:23p ORD
JetBlue direct (2h55m)

inbound: Aug 9, 2020
4:24a ORD » 6:50a BOS
JetBlue direct (2h26m)

$154

outward: Mar 19, 2020
11:28a BOS » 2:30p ORD
JetBlue direct (3h02m)

inbound: Mar 30, 2020
1:00p ORD » 3:23p BOS
JetBlue direct (2h23m)

$154

outward: Mar 19, 2020
11:28a BOS » 2:30p ORD
JetBlue direct (3h02m)

inbound: Mar 30, 2020
1:00p ORD » 3:23p BOS
JetBlue direct (2h23m)

$163

outward: Feb 27, 2020
5:00p BOS » 8:09p ORD
American Airlines direct (3h09m)

inbound: Feb 28, 2020
10:45p ORD » 4:58a BOS
American Airlines 1 stop (6h13m)

$167

outward: Sep 8, 2020
12:00p BOS » 3:03p ORD
Delta Air Lines direct (3h03m)

inbound: Sep 15, 2020
1:00p ORD » 3:35p BOS
Delta Air Lines direct (2h35m)

$180

outward: Jul 1, 2020
1:02p BOS » 4:02p ORD
United Airlines direct (3h)

inbound: Jul 9, 2020
4:05a ORD » 6:19a BOS
United Airlines direct (2h14m)

$199

outward: Jul 13, 2020
11:30a BOS » 2:10p MDW
Southwest Airlines direct (2h40m)

inbound: Jul 16, 2020
4:05a ORD » 6:19a BOS
United Airlines direct (2h14m)

$232

outward: Mar 10, 2020
12:56a BOS » 3:53a ORD
JetBlue direct (2h57m)

inbound: Mar 14, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)

$263

outward: Mar 15, 2020
11:28a BOS » 2:30p ORD
JetBlue direct (3h02m)

inbound: Mar 22, 2020
12:00p ORD » 2:23p BOS
JetBlue direct (2h23m)

$306

outward: Jun 18, 2020
12:28p BOS » 3:25p ORD
JetBlue direct (2h57m)

inbound: Jun 22, 2020
12:20a ORD » 4:33p BOS
Sun Country 1 stop (16h13m)

$325

outward: Mar 13, 2020
11:10a BOS » 2:18p ORD
Delta Air Lines direct (3h08m)

inbound: Mar 22, 2020
1:25p MDW » 3:40p BOS
Southwest Airlines direct (2h15m)

$344

outward: Jul 1, 2020
12:28p BOS » 3:23p ORD
JetBlue direct (2h55m)

inbound: Jul 11, 2020
3:58p ORD » 6:24p BOS
JetBlue direct (2h26m)

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

JetBlue

outbound: Mar 2, 2020
JetBlue direct

return: Mar 9, 2020
JetBlue direct

Spirit Airlines

outbound: May 11, 2020
Spirit Airlines direct

return: May 18, 2020
Spirit Airlines 1 stop

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

Travel tips for flights Boston - Chicago

Average flight duration: 2h42m (direct flight)

Arrival city:
Chicago, USA
Airport(s):
Midway International Airport (MDW)
O'Hare International Airport (ORD)
Local time:
Feb 25, 2020 4:48 PM, GMT-6
Weather:
min. 29ºF, max. 33ºF

Departure city:
Boston, USA
Airport(s):
Logan International Airport (BOS)
Manchester–Boston Regional Airport (MHT)
Local time:
Feb 25, 2020 5:48 PM, GMT-5
Weather:
min. 35ºF, max. 46ºF

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