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: Sat May 14 2016 Return: Tue May 17 2016 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 23m
nonstop
Depart: Tue May 17 2016 Return: Wed May 18 2016 Trip spans 2 days
United
United
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 24m
nonstop
Depart: Wed Jun 1 2016 Return: Sat Jun 11 2016 Trip spans 11 days
American Airlines
American Airlines
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Tue Oct 4 2016 Return: Tue Oct 11 2016 Trip spans 8 days
Major Airline
Major Airline
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 19m
nonstop
Depart: Sun May 8 2016 Return: Tue May 10 2016 Trip spans 3 days
Southwest
Southwest
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 15m
nonstop
Depart: Tue May 3 2016 Return: Wed May 4 2016 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 23m
nonstop
Depart: Sat Apr 30 2016 Return: Tue May 3 2016 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 23m
nonstop
Depart: Tue May 31 2016 Return: Wed Jun 1 2016 Trip spans 2 days
Delta
Delta
BOS
MDW
6h 12m
1 stop
MDW
BOS
4h 30m
1 stop
Depart: Thu Oct 6 2016 Return: Sun Oct 9 2016 Trip spans 4 days
Major Airline
Major Airline
BOS
ORD
2h 42m
nonstop
ORD
BOS
2h 20m
nonstop
Depart: Thu Oct 20 2016 Return: Mon Oct 24 2016 Trip spans 5 days
Major Airline
Major Airline
BOS
ORD
2h 41m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Wed Jun 22 2016 Return: Tue Jun 28 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 24m
nonstop
Depart: Mon Oct 24 2016 Return: Tue Oct 25 2016 Trip spans 2 days
Major Airline
Major Airline
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 19m
nonstop
Depart: Thu Jun 9 2016 Return: Mon Jun 13 2016 Trip spans 5 days
Southwest
Southwest
BOS
MDW
2h 40m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Wed Jul 27 2016 Return: Wed Aug 3 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 24m
nonstop
Depart: Tue Aug 9 2016 Return: Tue Aug 16 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 24m
nonstop
Depart: Tue Jul 19 2016 Return: Thu Jul 21 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Sat Aug 27 2016 Return: Fri Sep 2 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 24m
nonstop
Depart: Sun Sep 4 2016 Return: Sun Sep 11 2016 Trip spans 8 days
Southwest
Southwest
BOS
MDW
2h 35m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Fri Jun 3 2016 Return: Tue Jun 14 2016 Trip spans 12 days
Delta
Delta
BOS
MDW
4h 16m
1 stop
MDW
BOS
4h 01m
1 stop
Depart: Tue Aug 30 2016 Return: Sun Sep 4 2016 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 24m
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 7:19 am May 5 - Jun 1
1155 5:30 am 7:15 am Jun 2 - Jul 1
1404 7:00 am 8:58 am Jun 2 - Jul 2
1404 7:00 am 8:56 am May 5 - Jun 1
1435 9:00 am 10:49 am Jun 4 - Aug 20
1435 9:00 am 10:49 am Jun 2 - Jul 1
1435 9:00 am 10:58 am May 7 - May 28
1435 9:00 am 10:58 am May 5 - Jun 1
2253 10:00 am 11:43 am Jun 2 - Jun 3
2253 10:00 am 11:53 am May 5 - Jun 1
2253 10:00 am 11:43 am Jun 5 - Jul 8
1240 11:00 am 12:45 pm Jun 4 - Jun 25
1240 12:15 pm 2:04 pm Jun 2 - Jun 3
1240 12:15 pm 2:04 pm Jun 6 - Jun 30
1240 12:15 pm 2:04 pm Jun 5 - Jun 26
1299 12:20 pm 2:11 pm May 7 - May 28
1299 12:20 pm 2:11 pm May 5 - Jun 1
252 2:05 pm 3:58 pm May 5 - Jun 1
252 2:10 pm 4:01 pm Jun 2 - Jun 30
1051 3:30 pm 5:24 pm May 7 - May 28
197 3:51 pm 5:45 pm May 5 - Jun 1
197 3:52 pm 5:45 pm Jun 2 - Aug 22
2591 4:30 pm 6:26 pm Jun 2 - Jun 13
2224 4:59 pm 6:53 pm May 5 - May 12
2224 4:59 pm 6:53 pm May 6 - May 13
2224 4:59 pm 6:53 pm May 7 - May 28
2224 4:59 pm 6:53 pm May 15 - May 29
2224 4:59 pm 6:53 pm May 16 - Jun 1
1503 5:24 pm 7:24 pm Jun 2 - Jun 2
1503 5:24 pm 7:24 pm Jun 3 - Jun 10
1503 5:27 pm 7:27 pm Jun 4 - Jun 25
1503 5:59 pm 7:59 pm May 5 - Jun 1
1503 5:59 pm 7:59 pm May 7 - May 28
40 7:00 pm 8:54 pm May 5 - Jun 1
40 7:10 pm 8:58 pm Jun 2 - Jun 10
40 7:10 pm 8:58 pm Jun 5 - Jun 26
2503 9:10 pm 10:59 pm Jun 2 - Jun 8
* 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
$76
Destination

Chicago
only $76
only $131