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: Sat Feb 27 2016 Return: Sun Feb 28 2016 Trip spans 2 days
American Airlines
American Airlines
BOS
ORD
3h 00m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Wed Mar 2 2016 Return: Sun Mar 6 2016 Trip spans 5 days
American Airlines
American Airlines
BOS
ORD
3h 05m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Thu Mar 3 2016 Return: Mon Mar 7 2016 Trip spans 5 days
American Airlines
American Airlines
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 08m
nonstop
Depart: Wed Apr 6 2016 Return: Sun Apr 10 2016 Trip spans 5 days
American Airlines
American Airlines
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Sun Apr 24 2016 Return: Tue May 3 2016 Trip spans 10 days
American Airlines
American Airlines
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Sun Jul 24 2016 Return: Mon Aug 1 2016 Trip spans 9 days
American Airlines
American Airlines
BOS
ORD
2h 39m
nonstop
ORD
BOS
2h 19m
nonstop
Depart: Wed Mar 30 2016 Return: Sat Apr 2 2016 Trip spans 4 days
United
United
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 25m
nonstop
Depart: Sat Apr 30 2016 Return: Tue May 3 2016 Trip spans 4 days
United
United
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 20m
nonstop
Depart: Sat May 7 2016 Return: Sun May 8 2016 Trip spans 2 days
United
United
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Tue May 10 2016 Return: Sun May 15 2016 Trip spans 6 days
United
United
BOS
ORD
2h 40m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Wed Jun 1 2016 Return: Sat Jun 4 2016 Trip spans 4 days
United
United
BOS
ORD
2h 44m
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: 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: Sat May 21 2016 Return: Sun May 22 2016 Trip spans 2 days
United
United
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Sat Jun 11 2016 Return: Tue Jun 14 2016 Trip spans 4 days
United
United
BOS
ORD
2h 43m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Wed Mar 9 2016 Return: Sun Mar 13 2016 Trip spans 5 days
United
United
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 17m
nonstop
Depart: Fri Apr 1 2016 Return: Mon Apr 4 2016 Trip spans 4 days
American Airlines
American Airlines
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 08m
nonstop
Depart: Sat Jul 2 2016 Return: Sun Jul 10 2016 Trip spans 9 days
American Airlines
American Airlines
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Sun Jul 3 2016 Return: Wed Jul 6 2016 Trip spans 4 days
United
United
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 19m
nonstop
Depart: Mon Mar 21 2016 Return: Wed Mar 23 2016 Trip spans 3 days
Delta
Delta
BOS
MDW
4h 15m
1 stop
MDW
BOS
3h 47m
1 stop
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 Mar 3 - Mar 12
1155 5:30 am 7:29 am Feb 11 - Mar 2
1155 5:30 am 7:29 am Mar 13 - Apr 4
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 19 - Apr 2
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 Mar 19 - Apr 2
1435 8:55 am 10:53 am Feb 6 - Feb 27
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 Feb 4 - Mar 4
2253 10:00 am 11:58 am Mar 6 - Mar 11
2253 10:00 am 11:58 am Mar 13 - Mar 25
1299 12:15 pm 2:14 pm Feb 11 - Mar 11
1299 12:15 pm 2:14 pm Mar 13 - Mar 25
1299 12:20 pm 2:19 pm Mar 19 - Mar 19
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 Feb 5 - Feb 29
1404 2:00 pm 4:02 pm Mar 1 - Mar 2
252 2:00 pm 4:02 pm Mar 3 - Mar 11
252 2:00 pm 4:02 pm Mar 14 - Mar 25
252 2:00 pm 4:02 pm Mar 13 - Mar 13
197 3:45 pm 5:45 pm Mar 15 - Mar 24
197 3:45 pm 5:45 pm Mar 5 - Mar 12
197 3:45 pm 5:45 pm Mar 3 - Mar 10
197 3:45 pm 5:45 pm Mar 19 - Mar 19
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 13 - Mar 25
197 3:45 pm 5:45 pm Mar 4 - Mar 11
40 6:56 pm 9:08 pm Mar 13 - Apr 4
40 6:56 pm 9:08 pm Mar 19 - Mar 19
40 6:56 pm 9:08 pm Feb 4 - Mar 11
40 6:56 pm 9:08 pm Feb 13 - Mar 12
* 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.

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
$103
Destination

Chicago
only $103
only $204