Find Cheap Flights to Chicago

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 to Chicago

(Round-trip)
Depart: Sat Jul 8 2017 Return: Tue Aug 1 2017 Trip spans 25 days
United
United
BOS
ORD
2h 45m
nonstop
ORD
BOS
2h 20m
nonstop
Depart: Wed Nov 29 2017 Return: Wed Dec 6 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 22m
nonstop
Depart: Sat Dec 2 2017 Return: Mon Dec 4 2017 Trip spans 3 days
American Airlines
American Airlines
BOS
ORD
2h 46m
nonstop
ORD
BOS
2h 27m
nonstop
Depart: Tue Jul 11 2017 Return: Fri Jul 14 2017 Trip spans 4 days
Major Airline
Major Airline
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 24m
nonstop
Depart: Tue Aug 22 2017 Return: Tue Aug 29 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ATL
ORD
2h 10m
nonstop
ORD
ATL
1h 52m
nonstop
Depart: Sun Jul 30 2017 Return: Thu Aug 3 2017 Trip spans 5 days
Delta
Delta
ATL
ORD
2h 00m
nonstop
ORD
ATL
1h 58m
nonstop
Depart: Tue Oct 24 2017 Return: Tue Oct 31 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 11m
nonstop
Depart: Thu Sep 14 2017 Return: Sat Sep 16 2017 Trip spans 3 days
Major Airline
Major Airline
BOS
ORD
2h 53m
nonstop
ORD
BOS
2h 17m
nonstop
Depart: Tue Aug 29 2017 Return: Thu Sep 7 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
BOS
ORD
2h 55m
nonstop
ORD
BOS
2h 38m
nonstop
Depart: Sat Sep 2 2017 Return: Sun Sep 10 2017 Trip spans 9 days
Major Airline
Major Airline
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 20m
nonstop
Depart: Fri Sep 1 2017 Return: Sun Sep 3 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 32m
nonstop
Depart: Sun Dec 17 2017 Return: Wed Dec 20 2017 Trip spans 4 days
Major Airline
Major Airline
BOS
ORD
2h 58m
nonstop
ORD
BOS
2h 16m
nonstop
Depart: Mon Oct 9 2017 Return: Sat Oct 21 2017 Trip spans 13 days
Multiple Airlines
Multiple Airlines
BOS
ORD
2h 46m
nonstop
ORD
BOS
2h 20m
nonstop
Depart: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ATL
ORD
2h 09m
nonstop
ORD
ATL
1h 58m
nonstop
Depart: Thu Dec 7 2017 Return: Sun Dec 10 2017 Trip spans 4 days
American Airlines
American Airlines
BWI
ORD
2h 13m
nonstop
ORD
BWI
1h 57m
nonstop
Depart: Fri Oct 27 2017 Return: Mon Oct 30 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 46m
nonstop
ORD
BOS
2h 30m
nonstop
Depart: Thu Aug 3 2017 Return: Mon Aug 7 2017 Trip spans 5 days
United
United
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 22m
nonstop
Depart: Mon Aug 7 2017 Return: Wed Aug 9 2017 Trip spans 3 days
Major Airline
Major Airline
BWI
ORD
2h 09m
nonstop
ORD
BWI
1h 48m
nonstop
Depart: Sat Aug 26 2017 Return: Sun Aug 27 2017 Trip spans 2 days
Delta
Delta
ATL
ORD
2h 04m
nonstop
ORD
ATL
1h 55m
nonstop
Depart: Fri Aug 25 2017 Return: Sat Aug 26 2017 Trip spans 2 days
Multiple Airlines
Multiple Airlines
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 32m
nonstop
* 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

Baltimore
$151
Atlanta
$163
Boston
$113
Destination

Chicago
$113
Airlines Airline reviews

323 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 6.6.

Overall
7.0
Boarding
7.0
Crew
7.6
Comfort
6.4
Food
5.4
Entertainment
5.7