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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Boston Logan International to Chicago

(Round-trip)
Depart: Wed Aug 31 2016 Return: Wed Sep 14 2016 Trip spans 15 days
Depart: Sat Oct 22 2016 Return: Tue Oct 25 2016 Trip spans 4 days
Depart: Thu Sep 15 2016 Return: Sun Sep 18 2016 Trip spans 4 days
Depart: Fri Oct 28 2016 Return: Mon Oct 31 2016 Trip spans 4 days
Depart: Wed Sep 7 2016 Return: Tue Sep 13 2016 Trip spans 7 days
Depart: Wed Oct 26 2016 Return: Wed Nov 2 2016 Trip spans 8 days
Depart: Thu Oct 27 2016 Return: Sun Oct 30 2016 Trip spans 4 days
Depart: Wed Aug 31 2016 Return: Tue Oct 4 2016 Trip spans 35 days
Depart: Thu Dec 1 2016 Return: Mon Dec 5 2016 Trip spans 5 days
Depart: Wed Sep 7 2016 Return: Sat Sep 10 2016 Trip spans 4 days
Depart: Sun Aug 28 2016 Return: Wed Aug 31 2016 Trip spans 4 days
Depart: Tue Sep 13 2016 Return: Sat Sep 17 2016 Trip spans 5 days
Depart: Thu Sep 22 2016 Return: Sun Sep 25 2016 Trip spans 4 days
Depart: Thu Nov 3 2016 Return: Mon Nov 7 2016 Trip spans 5 days
Depart: Fri Oct 14 2016 Return: Sun Oct 16 2016 Trip spans 3 days
Depart: Thu Aug 25 2016 Return: Mon Aug 29 2016 Trip spans 5 days
Depart: Thu Aug 11 2016 Return: Sat Aug 13 2016 Trip spans 3 days
Depart: Mon Jul 25 2016 Return: Tue Aug 2 2016 Trip spans 9 days
Depart: Thu Aug 18 2016 Return: Fri Aug 19 2016 Trip spans 2 days
Depart: Sat Jul 30 2016 Return: Mon Aug 1 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 7:47 am Jul 28 - Aug 22
1155 6:00 am 7:50 am Aug 23 - Aug 23
1404 7:00 am 8:58 am Aug 23 - Sep 15
1404 7:10 am 9:08 am Jul 28 - Aug 22
1435 9:00 am 10:49 am Jul 28 - Aug 22
1435 9:00 am 10:49 am Jul 30 - Aug 20
1435 9:00 am 10:51 am Aug 23 - Sep 3
2253 10:00 am 11:43 am Jul 28 - Aug 22
2253 10:00 am 11:43 am Jul 31 - Aug 21
2253 10:05 am 11:57 am Aug 27 - Sep 3
2253 10:05 am 11:57 am Aug 28 - Aug 28
2253 10:05 am 11:57 am Aug 23 - Sep 2
1240 11:00 am 12:45 pm Aug 6 - Aug 20
1240 11:00 am 12:45 pm Jul 31 - Jul 31
1240 11:00 am 12:51 pm Aug 28 - Sep 4
1240 11:00 am 12:45 pm Aug 7 - Aug 21
1240 12:15 pm 2:04 pm Jul 28 - Aug 22
1240 12:15 pm 2:05 pm Aug 23 - Sep 15
252 2:10 pm 4:01 pm Jul 28 - Sep 2
197 3:30 pm 5:24 pm Aug 23 - Oct 21
197 3:52 pm 5:45 pm Jul 28 - Aug 22
2591 4:30 pm 6:24 pm Aug 23 - Sep 2
2591 4:30 pm 6:24 pm Aug 27 - Aug 27
2591 4:30 pm 6:26 pm Jul 28 - Aug 22
1503 5:24 pm 7:24 pm Aug 7 - Aug 22
1503 5:24 pm 7:24 pm Aug 9 - Aug 18
1503 5:24 pm 7:24 pm Aug 6 - Aug 20
1503 5:24 pm 7:24 pm Jul 29 - Aug 5
1503 5:24 pm 7:24 pm Jul 28 - Aug 4
1503 5:26 pm 7:20 pm Aug 23 - Aug 30
1503 5:26 pm 7:20 pm Aug 24 - Aug 31
1503 5:31 pm 7:25 pm Aug 27 - Aug 27
40 7:10 pm 8:58 pm Aug 8 - Aug 22
40 7:10 pm 8:58 pm Aug 7 - Aug 21
40 7:10 pm 8:58 pm Jul 30 - Aug 20
40 7:10 pm 8:58 pm Jul 28 - Aug 5
40 7:12 pm 9:02 pm Aug 27 - Aug 27
40 7:12 pm 9:02 pm Aug 23 - Aug 31
40 7:12 pm 9:02 pm Aug 25 - Sep 2
2503 9:10 pm 10:59 pm Jul 28 - Aug 19
2503 9:10 pm 10:59 pm Jul 31 - Aug 22
* 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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Boston
$77
Destination

Chicago
only $77
only $94