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: Tue May 2 2017 Return: Sat May 6 2017 Trip spans 5 days
United
United
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 17m
nonstop
Depart: Tue Apr 25 2017 Return: Tue May 2 2017 Trip spans 8 days
Major Airline
Major Airline
BOS
ORD
2h 56m
nonstop
ORD
BOS
2h 12m
nonstop
Depart: Tue May 16 2017 Return: Wed May 17 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 45m
nonstop
ORD
BOS
2h 32m
nonstop
Depart: Fri Mar 31 2017 Return: Tue Apr 4 2017 Trip spans 5 days
JetBlue
JetBlue
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 12m
nonstop
Depart: Tue Apr 4 2017 Return: Thu Apr 6 2017 Trip spans 3 days
Delta
Delta
BOS
MDW
6h 20m
1 stop
MDW
BOS
5h 03m
1 stop
Depart: Tue Jul 4 2017 Return: Tue Jul 11 2017 Trip spans 8 days
Major Airline
Major Airline
BOS
ORD
2h 52m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Mon Mar 27 2017 Return: Thu Mar 30 2017 Trip spans 4 days
American Airlines
American Airlines
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Tue Jul 11 2017 Return: Tue Jul 18 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 32m
nonstop
Depart: Tue Jun 6 2017 Return: Tue Jun 13 2017 Trip spans 8 days
Major Airline
Major Airline
BOS
ORD
3h 01m
nonstop
ORD
BOS
2h 31m
nonstop
Depart: Tue Aug 8 2017 Return: Tue Aug 15 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 32m
nonstop
Depart: Tue Aug 1 2017 Return: Tue Aug 15 2017 Trip spans 15 days
Major Airline
Major Airline
BOS
ORD
2h 55m
nonstop
ORD
BOS
2h 16m
nonstop
Depart: Wed Sep 6 2017 Return: Fri Sep 15 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 18m
nonstop
Depart: Wed Sep 13 2017 Return: Mon Sep 18 2017 Trip spans 6 days
Major Airline
Major Airline
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 18m
nonstop
Depart: Fri Apr 28 2017 Return: Tue May 2 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 45m
nonstop
ORD
BOS
2h 32m
nonstop
Depart: Tue May 2 2017 Return: Fri May 5 2017 Trip spans 4 days
Delta
Delta
BOS
MDW
6h 00m
1 stop
MDW
BOS
4h 17m
1 stop
Depart: Thu May 11 2017 Return: Mon May 22 2017 Trip spans 12 days
Major Airline
Major Airline
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 24m
nonstop
Depart: Thu Jun 1 2017 Return: Sat Jun 3 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 46m
nonstop
ORD
BOS
2h 31m
nonstop
Depart: Fri Mar 31 2017 Return: Mon Apr 3 2017 Trip spans 4 days
United
United
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 15m
nonstop
Depart: Wed May 3 2017 Return: Sat May 6 2017 Trip spans 4 days
Delta
Delta
BOS
MDW
6h 08m
1 stop
MDW
BOS
7h 00m
1 stop
Depart: Thu Jun 29 2017 Return: Tue Jul 4 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 47m
nonstop
ORD
BOS
2h 32m
nonstop
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1404 7:00 am 9:05 am Mar 23 - Apr 3
1404 7:00 am 8:55 am Apr 4 - Apr 4
1404 7:00 am 8:55 am Apr 5 - May 4
2459 9:25 am 11:20 am Apr 5 - May 4
2459 9:25 am 11:20 am Apr 8 - Apr 29
2253 10:20 am 12:15 pm Apr 25 - Apr 25
2253 10:20 am 12:15 pm Apr 26 - May 4
2253 10:20 am 12:19 pm Mar 26 - Apr 3
2253 10:20 am 12:15 pm Apr 4 - Apr 24
2253 10:35 am 12:30 pm Apr 8 - Apr 29
2253 10:35 am 12:34 pm Apr 1 - Apr 1
1240 12:00 pm 2:01 pm Mar 26 - Apr 2
1240 12:00 pm 2:01 pm Apr 3 - Apr 3
1240 12:00 pm 1:50 pm Apr 4 - Apr 10
1240 12:00 pm 1:50 pm Apr 11 - Apr 18
1240 12:00 pm 1:50 pm Apr 12 - Apr 24
1240 12:00 pm 1:50 pm Apr 25 - May 4
252 1:55 pm 3:54 pm Mar 26 - Apr 2
252 1:55 pm 3:54 pm Mar 27 - Apr 3
252 1:55 pm 3:52 pm Apr 4 - Apr 28
252 1:55 pm 3:52 pm Apr 30 - May 4
252 2:05 pm 4:06 pm Apr 1 - Apr 1
252 2:05 pm 3:57 pm Apr 8 - Apr 29
197 3:45 pm 5:43 pm Mar 23 - Apr 3
197 3:45 pm 5:38 pm Apr 4 - Apr 28
197 3:45 pm 5:38 pm Apr 30 - May 4
1530 5:15 pm 7:18 pm Mar 24 - Mar 31
1530 5:15 pm 7:18 pm Mar 27 - Apr 3
1530 5:20 pm 7:20 pm Apr 4 - May 2
1530 5:20 pm 7:20 pm Apr 5 - May 3
1530 5:20 pm 7:20 pm Apr 6 - Apr 27
40 7:06 pm 9:05 pm Mar 23 - Apr 3
40 7:10 pm 9:03 pm Apr 4 - May 4
* 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.

^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin

Boston
$103
Destination

Chicago
only $103
only $194
Airlines Airline reviews

258 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 6.0.

Overall
6.2
Boarding
6.4
Crew
7.0
Comfort
5.8
Food
4.8
Entertainment
5.0