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: Thu Mar 3 2016 Return: Fri Mar 4 2016 Trip spans 2 days
American Airlines
American Airlines
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Thu Mar 17 2016 Return: Wed Mar 23 2016 Trip spans 7 days
American Airlines
American Airlines
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Sun Mar 20 2016 Return: Wed Mar 23 2016 Trip spans 4 days
American Airlines
American Airlines
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Thu Apr 7 2016 Return: Sun Apr 10 2016 Trip spans 4 days
American Airlines
American Airlines
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Tue Apr 12 2016 Return: Sun Apr 17 2016 Trip spans 6 days
American Airlines
American Airlines
BOS
ORD
2h 53m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Sun May 8 2016 Return: Wed May 11 2016 Trip spans 4 days
American Airlines
American Airlines
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Thu Jun 16 2016 Return: Mon Jun 20 2016 Trip spans 5 days
American Airlines
American Airlines
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 19m
nonstop
Depart: Thu Feb 25 2016 Return: Sat Feb 27 2016 Trip spans 3 days
American Airlines
American Airlines
BOS
ORD
3h 05m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Thu May 5 2016 Return: Sun May 8 2016 Trip spans 4 days
American Airlines
American Airlines
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Wed Jun 1 2016 Return: Sun Jun 5 2016 Trip spans 5 days
United
United
BOS
ORD
2h 42m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Wed Jul 6 2016 Return: Tue Jul 12 2016 Trip spans 7 days
United
United
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 22m
nonstop
Depart: Fri Apr 8 2016 Return: Sun Apr 10 2016 Trip spans 3 days
American Airlines
American Airlines
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Tue Feb 23 2016 Return: Thu Feb 25 2016 Trip spans 3 days
Delta
Delta
BOS
MDW
4h 38m
1 stop
MDW
BOS
5h 23m
1 stop
Depart: Fri Feb 26 2016 Return: Thu Mar 3 2016 Trip spans 7 days
Delta
Delta
BOS
MDW
5h 52m
1 stop
MDW
BOS
3h 47m
1 stop
Depart: Sat Apr 30 2016 Return: Tue May 3 2016 Trip spans 4 days
Delta
Delta
BOS
MDW
4h 48m
1 stop
MDW
BOS
3h 59m
1 stop
Depart: Fri May 6 2016 Return: Tue May 10 2016 Trip spans 5 days
Delta
Delta
BOS
MDW
6h 15m
1 stop
MDW
BOS
4h 58m
1 stop
Depart: Tue Jun 7 2016 Return: Sat Jun 11 2016 Trip spans 5 days
Delta
Delta
BOS
MDW
6h 13m
1 stop
MDW
BOS
4h 51m
1 stop
Depart: Fri Mar 25 2016 Return: Sun Mar 27 2016 Trip spans 3 days
Delta
Delta
BOS
ORD
6h 00m
1 stop
ORD
BOS
4h 04m
1 stop
Depart: Fri Aug 26 2016 Return: Sun Aug 28 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 26m
nonstop
Depart: Fri Feb 12 2016 Return: Sun Feb 14 2016 Trip spans 3 days
Southwest
Southwest
BOS
MDW
2h 55m
nonstop
MDW
BOS
2h 15m
nonstop
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 7:29 am Feb 11 - Mar 2
1155 5:30 am 7:29 am Mar 13 - Apr 4
1155 5:30 am 7:29 am Mar 3 - Mar 12
1404 7:00 am 9:07 am Mar 13 - Apr 4
1404 7:00 am 9:07 am Mar 3 - Mar 11
2253 7:05 am 9:12 am Mar 5 - Mar 12
1435 8:55 am 10:53 am Mar 5 - Mar 12
1435 8:55 am 10:53 am Feb 6 - Feb 27
1435 9:00 am 11:05 am Feb 16 - Feb 16
1435 9:00 am 11:05 am Feb 4 - Feb 15
1435 9:00 am 11:05 am Feb 17 - Mar 11
1435 9:00 am 11:05 am Mar 13 - Mar 25
2253 10:00 am 11:58 am Mar 13 - Mar 25
2253 10:00 am 11:58 am Mar 6 - Mar 11
2253 10:00 am 11:58 am Feb 4 - Mar 4
1299 12:15 pm 2:14 pm Mar 13 - Mar 25
1299 12:15 pm 2:14 pm Feb 11 - Mar 11
1299 12:20 pm 2:19 pm Mar 5 - Mar 12
1299 12:20 pm 2:19 pm Feb 13 - Feb 27
1404 2:00 pm 4:02 pm Feb 4 - Feb 25
1404 2:00 pm 4:02 pm Mar 1 - Mar 2
1404 2:00 pm 4:02 pm Feb 5 - Feb 29
252 2:00 pm 4:02 pm Mar 14 - Mar 25
252 2:00 pm 4:02 pm Mar 3 - Mar 11
252 2:00 pm 4:02 pm Mar 13 - Mar 13
197 3:45 pm 5:45 pm Mar 13 - Mar 25
197 3:45 pm 5:45 pm Mar 15 - Mar 24
197 3:45 pm 5:45 pm Feb 4 - Mar 1
197 3:45 pm 5:45 pm Feb 5 - Mar 2
197 3:45 pm 5:45 pm Mar 3 - Mar 10
197 3:45 pm 5:45 pm Mar 5 - Mar 12
197 3:45 pm 5:45 pm Mar 4 - Mar 11
40 6:56 pm 9:08 pm Feb 4 - Mar 11
40 6:56 pm 9:08 pm Feb 13 - Mar 12
40 6:56 pm 9:08 pm Mar 13 - Apr 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.

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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
$163
Destination

Chicago
only $163
only $204