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: Mon Sep 12 2016 Return: Wed Sep 14 2016 Trip spans 3 days
Depart: Wed Oct 12 2016 Return: Sat Oct 15 2016 Trip spans 4 days
Depart: Wed Aug 31 2016 Return: Thu Sep 8 2016 Trip spans 9 days
Depart: Tue Sep 13 2016 Return: Mon Sep 19 2016 Trip spans 7 days
Depart: Sun Sep 18 2016 Return: Tue Sep 27 2016 Trip spans 10 days
Depart: Sat Oct 1 2016 Return: Mon Oct 3 2016 Trip spans 3 days
Depart: Tue Sep 27 2016 Return: Sun Oct 2 2016 Trip spans 6 days
Depart: Tue Oct 18 2016 Return: Thu Oct 27 2016 Trip spans 10 days
Depart: Sun Oct 16 2016 Return: Sat Oct 29 2016 Trip spans 14 days
Depart: Fri Sep 30 2016 Return: Mon Oct 3 2016 Trip spans 4 days
Depart: Wed Oct 19 2016 Return: Sat Oct 22 2016 Trip spans 4 days
Depart: Wed Aug 31 2016 Return: Wed Sep 14 2016 Trip spans 15 days
Depart: Mon Oct 24 2016 Return: Tue Nov 1 2016 Trip spans 9 days
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Depart: Tue Nov 1 2016 Return: Tue Nov 8 2016 Trip spans 8 days
Depart: Tue Sep 13 2016 Return: Sat Sep 17 2016 Trip spans 5 days
Depart: Wed Sep 21 2016 Return: Mon Sep 26 2016 Trip spans 6 days
Depart: Thu Oct 13 2016 Return: Mon Oct 17 2016 Trip spans 5 days
Depart: Fri Sep 2 2016 Return: Tue Sep 6 2016 Trip spans 5 days
Depart: Tue Oct 18 2016 Return: Thu Oct 20 2016 Trip spans 3 days
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1155 6:00 am 7:50 am Aug 25 - Sep 15
1155 6:00 am 7:50 am Sep 16 - Oct 28
1404 7:00 am 8:58 am Aug 25 - Sep 15
1404 7:00 am 8:58 am Sep 16 - Nov 3
1435 9:00 am 10:51 am Sep 16 - Oct 29
1435 9:00 am 10:51 am Sep 11 - Sep 15
1435 9:00 am 10:51 am Aug 25 - Sep 10
1435 9:00 am 10:51 am Sep 4 - Sep 4
2253 10:05 am 11:57 am Sep 17 - Oct 1
2253 10:05 am 11:57 am Sep 16 - Oct 5
2253 10:05 am 11:57 am Aug 25 - Sep 2
2253 10:05 am 11:57 am Aug 27 - Sep 3
2253 10:05 am 11:57 am Sep 5 - Sep 15
2253 10:05 am 11:57 am Sep 10 - Sep 10
1240 11:00 am 12:51 pm Aug 28 - Sep 4
1240 12:15 pm 2:05 pm Sep 16 - Oct 28
1240 12:15 pm 2:05 pm Sep 18 - Oct 2
1240 12:15 pm 2:05 pm Sep 11 - Sep 11
1240 12:15 pm 2:05 pm Aug 25 - Sep 15
252 2:10 pm 4:01 pm Aug 25 - Sep 2
252 2:10 pm 4:01 pm Sep 16 - Oct 22
252 2:10 pm 4:01 pm Sep 4 - Sep 15
252 2:10 pm 4:01 pm Sep 3 - Sep 3
197 3:30 pm 5:24 pm Sep 16 - Oct 21
197 3:30 pm 5:24 pm Aug 25 - Sep 15
2591 4:30 pm 6:24 pm Sep 5 - Sep 15
2591 4:30 pm 6:24 pm Sep 10 - Sep 10
2591 4:30 pm 6:24 pm Sep 4 - Sep 4
2591 4:30 pm 6:24 pm Sep 16 - Oct 5
2591 4:30 pm 6:24 pm Sep 17 - Oct 1
2591 4:30 pm 6:24 pm Aug 25 - Sep 2
1503 5:26 pm 7:20 pm Sep 5 - Sep 15
1503 5:26 pm 7:20 pm Sep 22 - Oct 13
1503 5:26 pm 7:20 pm Sep 16 - Oct 17
1503 5:26 pm 7:20 pm Sep 4 - Sep 4
1503 5:26 pm 7:20 pm Aug 26 - Sep 2
1503 5:31 pm 7:25 pm Sep 10 - Sep 10
1503 5:31 pm 7:25 pm Sep 17 - Oct 22
40 7:11 pm 9:01 pm Sep 7 - Oct 5
40 7:11 pm 9:01 pm Sep 10 - Oct 29
40 7:12 pm 9:02 pm Aug 25 - Sep 2
40 7:12 pm 9:02 pm Sep 5 - Sep 6
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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

Here's why:

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

We compile tonnes 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 can'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.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Boston
$77
Destination

Chicago
only $77
only $84