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: Tue Oct 4 2016 Return: Wed Oct 12 2016 Trip spans 9 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 26m
nonstop
Depart: Thu Oct 20 2016 Return: Tue Oct 25 2016 Trip spans 6 days
United
United
BOS
ORD
2h 45m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Sat Oct 29 2016 Return: Wed Nov 2 2016 Trip spans 5 days
JetBlue
JetBlue
BOS
ORD
2h 40m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Wed Nov 2 2016 Return: Sat Nov 5 2016 Trip spans 4 days
American Airlines
American Airlines
BOS
ORD
2h 54m
nonstop
ORD
BOS
2h 11m
nonstop
Depart: Thu Jan 19 2017 Return: Mon Jan 23 2017 Trip spans 5 days
Major Airline
Major Airline
BOS
ORD
3h 02m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Tue Nov 1 2016 Return: Wed Nov 2 2016 Trip spans 2 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 26m
nonstop
Depart: Wed Dec 7 2016 Return: Tue Dec 13 2016 Trip spans 7 days
JetBlue
JetBlue
BOS
ORD
2h 57m
nonstop
ORD
BOS
2h 11m
nonstop
Depart: Thu Oct 20 2016 Return: Tue Oct 25 2016 Trip spans 6 days
Delta
Delta
BOS
MDW
4h 21m
1 stop
MDW
BOS
6h 29m
1 stop
Depart: Wed Oct 5 2016 Return: Sat Oct 8 2016 Trip spans 4 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Thu Oct 20 2016 Return: Tue Oct 25 2016 Trip spans 6 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Wed Jan 4 2017 Return: Wed Jan 11 2017 Trip spans 8 days
JetBlue
JetBlue
BOS
ORD
3h 01m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Tue Oct 25 2016 Return: Sat Oct 29 2016 Trip spans 5 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Sat Mar 4 2017 Return: Sat Mar 11 2017 Trip spans 8 days
JetBlue
JetBlue
BOS
ORD
3h 00m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Wed Oct 26 2016 Return: Sat Oct 29 2016 Trip spans 4 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Wed Dec 28 2016 Return: Wed Jan 4 2017 Trip spans 8 days
United
United
BOS
ORD
2h 54m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Sat Oct 29 2016 Return: Sat Nov 5 2016 Trip spans 8 days
Major Airline
Major Airline
BOS
MDW
2h 50m
nonstop
MDW
BOS
2h 15m
nonstop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
JetBlue
JetBlue
BOS
ORD
2h 58m
nonstop
ORD
BOS
2h 16m
nonstop
Depart: Tue Nov 1 2016 Return: Thu Nov 3 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Fri Nov 4 2016 Return: Sun Nov 6 2016 Trip spans 3 days
American Airlines
American Airlines
BOS
ORD
3h 11m
nonstop
ORD
BOS
2h 08m
nonstop
Depart: Thu Mar 2 2017 Return: Mon Mar 6 2017 Trip spans 5 days
JetBlue
JetBlue
BOS
ORD
2h 58m
nonstop
ORD
BOS
2h 14m
nonstop
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1155 5:34 am 7:45 am Nov 4 - Nov 4
1155 6:00 am 7:50 am Nov 3 - Nov 3
1155 6:00 am 7:50 am Sep 29 - Oct 28
1404 7:00 am 9:11 am Nov 4 - Nov 5
1404 7:00 am 8:58 am Sep 29 - Nov 3
1435 9:00 am 10:58 am Nov 4 - Nov 5
1435 9:00 am 10:51 am Oct 30 - Nov 3
1435 9:00 am 10:51 am Sep 29 - Oct 29
2253 10:05 am 11:57 am Sep 29 - Oct 5
2253 10:07 am 11:59 am Oct 29 - Nov 3
2253 10:07 am 11:59 am Oct 8 - Oct 22
2253 10:07 am 11:59 am Oct 6 - Oct 28
2253 10:10 am 12:10 pm Nov 4 - Nov 4
1240 12:00 pm 1:53 pm Nov 4 - Nov 4
1240 12:15 pm 2:05 pm Oct 9 - Oct 23
1240 12:15 pm 2:05 pm Nov 1 - Nov 3
1240 12:15 pm 2:05 pm Sep 29 - Oct 28
1240 12:15 pm 2:05 pm Oct 30 - Oct 30
252 1:50 pm 3:52 pm Nov 4 - Nov 4
252 2:10 pm 4:01 pm Oct 23 - Oct 30
252 2:10 pm 4:01 pm Oct 31 - Oct 31
252 2:10 pm 4:01 pm Nov 1 - Nov 3
252 2:10 pm 4:01 pm Sep 29 - Oct 22
197 3:10 pm 5:12 pm Nov 4 - Nov 4
197 3:30 pm 5:24 pm Sep 29 - Oct 21
197 3:30 pm 5:24 pm Oct 23 - Nov 3
2591 4:10 pm 6:11 pm Nov 4 - Nov 4
2591 4:20 pm 6:14 pm Oct 29 - Nov 3
2591 4:20 pm 6:14 pm Oct 6 - Oct 28
2591 4:20 pm 6:14 pm Oct 8 - Oct 22
2591 4:30 pm 6:24 pm Sep 29 - Oct 5
1503 5:15 pm 7:23 pm Nov 4 - Nov 4
1503 5:26 pm 7:20 pm Sep 29 - Oct 13
1503 5:26 pm 7:20 pm Oct 31 - Oct 31
1503 5:26 pm 7:20 pm Nov 2 - Nov 2
1503 5:26 pm 7:20 pm Oct 19 - Oct 30
1503 5:26 pm 7:20 pm Oct 18 - Nov 3
1503 5:26 pm 7:20 pm Sep 30 - Oct 17
1503 5:31 pm 7:25 pm Oct 1 - Oct 22
1503 5:31 pm 7:25 pm Oct 29 - Oct 29
40 7:11 pm 9:01 pm Nov 1 - Nov 3
40 7:11 pm 9:01 pm Sep 29 - Oct 5
40 7:11 pm 9:01 pm Oct 7 - Oct 28
40 7:11 pm 9:05 pm Nov 4 - Nov 4
40 7:11 pm 9:01 pm Oct 1 - Oct 29
40 7:25 pm 9:15 pm Oct 9 - Oct 9
40 7:25 pm 9:15 pm Oct 23 - Oct 30
40 8:47 pm 10:41 pm Oct 16 - Oct 16
40 9:23 pm 11:14 pm Oct 6 - Oct 6
* 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,
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^ 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
$80
Destination

Chicago
only $80
only $104
Airlines Airline reviews

195 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
4.9