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

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 Chicago to Boston Logan International

(Round-trip)
Depart: Tue Aug 23 2016 Return: Wed Aug 24 2016 Trip spans 2 days
Depart: Wed Aug 24 2016 Return: Sat Sep 3 2016 Trip spans 11 days
Depart: Sun May 29 2016 Return: Wed Jun 8 2016 Trip spans 11 days
Depart: Wed Jul 13 2016 Return: Wed Jul 20 2016 Trip spans 8 days
Depart: Fri Jun 17 2016 Return: Sat Jun 18 2016 Trip spans 2 days
Depart: Mon Oct 24 2016 Return: Wed Nov 9 2016 Trip spans 17 days
Depart: Tue Jun 14 2016 Return: Wed Jun 15 2016 Trip spans 2 days
Depart: Wed Sep 14 2016 Return: Sat Sep 17 2016 Trip spans 4 days
Depart: Sat Oct 22 2016 Return: Sat Oct 29 2016 Trip spans 8 days
Depart: Wed Sep 7 2016 Return: Tue Sep 13 2016 Trip spans 7 days
Depart: Fri Sep 9 2016 Return: Sat Sep 17 2016 Trip spans 9 days
Depart: Tue Sep 27 2016 Return: Tue Oct 4 2016 Trip spans 8 days
Depart: Tue Sep 13 2016 Return: Thu Sep 22 2016 Trip spans 10 days
Depart: Fri Sep 30 2016 Return: Tue Oct 4 2016 Trip spans 5 days
Depart: Thu Sep 29 2016 Return: Sat Oct 1 2016 Trip spans 3 days
Depart: Mon Oct 17 2016 Return: Fri Oct 28 2016 Trip spans 12 days
Depart: Fri Nov 4 2016 Return: Sun Nov 6 2016 Trip spans 3 days
Depart: Thu Nov 3 2016 Return: Sun Nov 6 2016 Trip spans 4 days
Depart: Fri Oct 28 2016 Return: Mon Oct 31 2016 Trip spans 4 days
Depart: Sat Oct 29 2016 Return: Sat Nov 5 2016 Trip spans 8 days
Direct flights CHI to BOS on American Airlines
Flight # Depart ORD Arrive BOS Sun Mon Tue Wed Thu Fri Sat Valid Between
1183 6:00 am 9:11 am Jun 4 - Jun 4
1183 6:00 am 9:11 am Jun 10 - Jul 1
1183 6:00 am 9:11 am Jul 5 - Aug 22
1183 6:00 am 9:11 am Jun 13 - Jun 30
1183 6:00 am 9:11 am Jun 11 - Jun 25
1183 6:00 am 9:11 am Jun 2 - Jun 9
1240 7:00 am 10:14 am Jul 2 - Jul 2
1240 7:00 am 10:14 am Jun 4 - Jun 25
1240 7:00 am 10:14 am Jul 1 - Jul 1
1240 7:00 am 10:14 am Jun 6 - Jun 30
2607 7:00 am 10:14 am Jun 5 - Jun 26
1240 7:05 am 10:19 am Jul 5 - Aug 22
1257 8:30 am 11:46 am Jun 2 - Jul 4
1257 8:35 am 11:51 am Jul 5 - Aug 22
252 10:05 am 1:21 pm Jun 2 - Jun 30
252 10:05 am 1:21 pm Jul 1 - Aug 22
2224 11:49 am 3:05 pm Jun 2 - Aug 22
197 12:05 pm 3:26 pm Jun 4 - Aug 20
1503 1:20 pm 4:38 pm Jun 3 - Jun 10
1503 1:20 pm 4:38 pm Jun 13 - Aug 5
1503 1:20 pm 4:38 pm Jun 7 - Aug 4
1503 1:24 pm 4:42 pm Jul 2 - Jul 2
1503 1:24 pm 4:42 pm Jun 4 - Jun 25
2387 3:05 pm 6:25 pm Jun 4 - Jun 4
2387 3:05 pm 6:25 pm Jun 5 - Jun 5
2387 3:05 pm 6:25 pm Jun 11 - Jun 25
2387 3:05 pm 6:25 pm Jun 12 - Jun 26
2387 3:05 pm 6:25 pm Jun 7 - Jun 7
2387 3:05 pm 6:25 pm Jun 14 - Jul 1
2387 3:05 pm 6:25 pm Jul 2 - Jul 2
2387 3:05 pm 6:25 pm Jul 3 - Aug 5
2387 3:05 pm 6:25 pm Jun 6 - Jun 13
1205 4:55 pm 8:16 pm Jul 5 - Aug 22
1205 4:55 pm 8:16 pm Jun 5 - Jul 4
1205 4:55 pm 8:16 pm Jun 2 - Jun 4
366 6:36 pm 9:59 pm Jun 2 - Jul 1
366 6:36 pm 9:59 pm Jul 4 - Aug 22
2326 8:25 pm 11:43 pm Jun 9 - Jun 30
2326 8:25 pm 11:43 pm Jun 10 - Jun 29
2326 8:25 pm 11:43 pm Jul 1 - Jul 1
2326 8:25 pm 11:43 pm Jul 3 - Jul 3
2326 8:25 pm 11:43 pm Jun 2 - Jun 8
2326 8:25 pm 11:43 pm Jul 4 - Aug 5
2326 8:25 pm 11:43 pm Jul 5 - Aug 4
1167 9:44 pm 12:59 am Jul 4 - Aug 22
1167 9:44 pm 12:59 am Jun 2 - Jul 1
* 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

Chicago
only $83
only $165
Destination

Boston
$83