Find Deals on Flights from Boston Logan International to Chicago (BOS - CHI)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Boston Logan International to Chicago

(Round-trip)
Depart: Tue Aug 23 2016 Return: Wed Aug 24 2016 Trip spans 2 days
Depart: Tue May 31 2016 Return: Sat Jun 4 2016 Trip spans 5 days
Depart: Tue Jun 7 2016 Return: Wed Jun 8 2016 Trip spans 2 days
Depart: Thu Aug 4 2016 Return: Thu Aug 25 2016 Trip spans 22 days
Depart: Fri Nov 11 2016 Return: Mon Nov 14 2016 Trip spans 4 days
Depart: Wed Aug 24 2016 Return: Wed Aug 31 2016 Trip spans 8 days
Depart: Fri Sep 2 2016 Return: Tue Sep 6 2016 Trip spans 5 days
Depart: Fri Sep 30 2016 Return: Tue Oct 4 2016 Trip spans 5 days
Depart: Wed Jun 15 2016 Return: Wed Jun 22 2016 Trip spans 8 days
Depart: Thu Oct 20 2016 Return: Tue Oct 25 2016 Trip spans 6 days
Depart: Fri Oct 28 2016 Return: Mon Oct 31 2016 Trip spans 4 days
Depart: Wed Nov 2 2016 Return: Mon Nov 7 2016 Trip spans 6 days
Depart: Fri Jun 10 2016 Return: Thu Jun 16 2016 Trip spans 7 days
Depart: Thu Aug 18 2016 Return: Wed Aug 24 2016 Trip spans 7 days
Depart: Thu Jun 2 2016 Return: Fri Jun 3 2016 Trip spans 2 days
Depart: Sun Sep 4 2016 Return: Tue Sep 6 2016 Trip spans 3 days
Depart: Wed Sep 7 2016 Return: Sat Sep 10 2016 Trip spans 4 days
Depart: Wed Aug 31 2016 Return: Fri Sep 2 2016 Trip spans 3 days
Depart: Sat Nov 12 2016 Return: Mon Nov 14 2016 Trip spans 3 days
Depart: Thu Jul 28 2016 Return: Tue Aug 23 2016 Trip spans 27 days
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1155 5:30 am 7:15 am Jun 2 - Jul 1
1155 6:00 am 7:47 am Jul 5 - Aug 22
1404 7:00 am 8:58 am Jun 2 - Jul 2
1404 7:10 am 9:08 am Jul 5 - Aug 22
1435 9:00 am 10:49 am Jun 2 - Jul 1
1435 9:00 am 10:49 am Jun 4 - Aug 20
1435 9:00 am 10:49 am Jul 4 - Aug 22
2253 10:00 am 11:43 am Jun 5 - Jul 8
1240 11:00 am 12:45 pm Jun 4 - Jun 25
1240 11:00 am 12:45 pm Jul 2 - Jul 2
1240 12:15 pm 2:04 pm Jul 1 - Jul 1
1240 12:15 pm 2:04 pm Jul 3 - Jul 4
1240 12:15 pm 2:04 pm Jun 5 - Jun 26
1240 12:15 pm 2:04 pm Jul 5 - Aug 22
1240 12:15 pm 2:04 pm Jun 6 - Jun 30
252 2:10 pm 4:01 pm Jul 1 - Aug 22
252 2:10 pm 4:01 pm Jun 2 - Jun 30
8640 3:15 pm 5:05 pm Jun 7 - Jun 7
197 3:52 pm 5:45 pm Jun 2 - Aug 22
2591 4:30 pm 6:26 pm Jun 7 - Jun 7
2591 4:30 pm 6:26 pm Jun 2 - Jun 13
2591 4:30 pm 6:26 pm Jun 14 - Aug 22
1503 5:24 pm 7:24 pm Jun 7 - Aug 4
1503 5:24 pm 7:24 pm Jun 3 - Jun 10
1503 5:24 pm 7:24 pm Jun 13 - Aug 5
1503 5:27 pm 7:27 pm Jul 2 - Jul 2
1503 5:27 pm 7:27 pm Jun 4 - Jun 25
40 7:10 pm 8:58 pm Jun 13 - Jul 8
40 7:10 pm 8:58 pm Jun 5 - Jun 26
40 7:10 pm 8:58 pm Jun 11 - Jun 25
40 7:10 pm 8:58 pm Jun 2 - Jun 10
2503 9:10 pm 10:59 pm Jul 5 - Aug 22
2503 9:10 pm 10:59 pm Jun 2 - Jun 8
2503 9:10 pm 10:59 pm Jun 9 - Jul 1
2503 9:10 pm 10:59 pm Jun 12 - Jun 29
2503 9:10 pm 10:59 pm Jul 4 - Jul 4
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we don't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find on occasion that certain prices are no longer available.

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Airports
Origin

Boston
$81
Destination

Chicago
only $81
only $169