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: Mon Oct 3 2016 Return: Tue Oct 4 2016 Trip spans 2 days
Major Airline
Major Airline
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 16m
nonstop
Depart: Wed Sep 28 2016 Return: Wed Oct 19 2016 Trip spans 22 days
American Airlines
American Airlines
BOS
ORD
2h 51m
nonstop
ORD
BOS
2h 18m
nonstop
Depart: Thu Nov 3 2016 Return: Mon Nov 7 2016 Trip spans 5 days
United
United
BOS
ORD
2h 55m
nonstop
ORD
BOS
2h 15m
nonstop
Depart: Thu Nov 3 2016 Return: Mon Nov 7 2016 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 26m
nonstop
Depart: Wed Dec 14 2016 Return: Wed Jan 4 2017 Trip spans 22 days
JetBlue
JetBlue
BOS
ORD
2h 57m
nonstop
ORD
BOS
2h 22m
nonstop
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
Southwest
Southwest
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Wed Nov 2 2016 Return: Sat Nov 5 2016 Trip spans 4 days
Major Airline
Major Airline
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 11m
nonstop
Depart: Tue Nov 8 2016 Return: Wed Nov 16 2016 Trip spans 9 days
Major Airline
Major Airline
BOS
ORD
2h 57m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Thu Nov 10 2016 Return: Wed Nov 16 2016 Trip spans 7 days
Major Airline
Major Airline
BOS
ORD
3h 00m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
JetBlue
JetBlue
BOS
ORD
3h 00m
nonstop
ORD
BOS
2h 15m
nonstop
Depart: Fri Oct 21 2016 Return: Tue Oct 25 2016 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 26m
nonstop
Depart: Wed Oct 26 2016 Return: Mon Oct 31 2016 Trip spans 6 days
Major Airline
Major Airline
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 26m
nonstop
Depart: Fri Mar 3 2017 Return: Mon Mar 6 2017 Trip spans 4 days
JetBlue
JetBlue
BOS
ORD
2h 58m
nonstop
ORD
BOS
2h 16m
nonstop
Depart: Thu Dec 8 2016 Return: Mon Dec 12 2016 Trip spans 5 days
Major Airline
Major Airline
BOS
ORD
3h 00m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Wed Feb 15 2017 Return: Sun Feb 19 2017 Trip spans 5 days
United
United
BOS
ORD
2h 43m
nonstop
ORD
BOS
2h 14m
nonstop
Depart: Wed Oct 5 2016 Return: Wed Oct 12 2016 Trip spans 8 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Mon Oct 17 2016 Return: Thu Oct 20 2016 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 50m
nonstop
ORD
BOS
2h 26m
nonstop
Depart: Wed Oct 19 2016 Return: Mon Oct 24 2016 Trip spans 6 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Thu Oct 20 2016 Return: Sat Oct 22 2016 Trip spans 3 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Depart: Tue Oct 25 2016 Return: Wed Nov 2 2016 Trip spans 9 days
Major Airline
Major Airline
BOS
MDW
2h 45m
nonstop
MDW
BOS
2h 10m
nonstop
Direct flights BOS to CHI on American Airlines
Flight # Depart BOS Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
1155 6:00 am 7:50 am Sep 22 - Oct 28
1404 7:00 am 8:58 am Sep 22 - Nov 3
1435 9:00 am 10:51 am Oct 30 - Nov 3
1435 9:00 am 10:51 am Sep 22 - Oct 29
2253 10:05 am 11:57 am Sep 22 - Oct 5
2253 10:05 am 11:57 am Sep 24 - Oct 1
2253 10:07 am 11:59 am Oct 8 - Oct 22
2253 10:07 am 11:59 am Oct 29 - Nov 3
2253 10:07 am 11:59 am Oct 6 - Oct 28
1240 12:15 pm 2:05 pm Oct 9 - Oct 23
1240 12:15 pm 2:05 pm Oct 30 - Oct 30
1240 12:15 pm 2:05 pm Sep 25 - Oct 2
1240 12:15 pm 2:05 pm Sep 22 - Oct 28
252 2:10 pm 4:01 pm Sep 22 - Oct 22
252 2:10 pm 4:01 pm Oct 23 - Oct 30
252 2:10 pm 4:01 pm Oct 31 - Oct 31
197 3:30 pm 5:24 pm Oct 23 - Nov 3
197 3:30 pm 5:24 pm Sep 22 - Oct 21
2591 4:20 pm 6:14 pm Oct 6 - Oct 28
2591 4:20 pm 6:14 pm Oct 8 - Oct 22
2591 4:20 pm 6:14 pm Oct 29 - Nov 3
2591 4:30 pm 6:24 pm Sep 24 - Oct 1
2591 4:30 pm 6:24 pm Sep 22 - Oct 5
1503 5:26 pm 7:20 pm Sep 23 - Oct 17
1503 5:26 pm 7:20 pm Oct 18 - Nov 3
1503 5:26 pm 7:20 pm Sep 22 - Oct 13
1503 5:26 pm 7:20 pm Oct 31 - Oct 31
1503 5:26 pm 7:20 pm Oct 19 - Oct 30
1503 5:31 pm 7:25 pm Sep 24 - Oct 22
1503 5:31 pm 7:25 pm Oct 29 - Oct 29
40 7:11 pm 9:01 pm Sep 24 - Oct 29
40 7:11 pm 9:01 pm Sep 22 - Oct 5
40 7:11 pm 9:01 pm Oct 7 - Oct 28
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.

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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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Airports
Origin

Boston
$81
Destination

Chicago
only $81
only $104
Airlines Airline reviews

197 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 6.1.

Overall
6.3
Boarding
6.5
Crew
7.1
Comfort
5.9
Food
4.8
Entertainment
5.0