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
Students
under 26
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: Fri Jan 27 2017 Return: Mon Jan 30 2017 Trip spans 4 days
Major Airline
Major Airline
BOS
ORD
2h 58m
nonstop
ORD
BOS
2h 15m
nonstop
Depart: Mon Jan 30 2017 Return: Tue Jan 31 2017 Trip spans 2 days
JetBlue
JetBlue
BOS
ORD
2h 58m
nonstop
ORD
BOS
2h 15m
nonstop
Depart: Sat May 13 2017 Return: Wed May 17 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 28m
nonstop
Depart: Fri Jul 21 2017 Return: Mon Jul 24 2017 Trip spans 4 days
Southwest
Southwest
BOS
MDW
5h 25m
1 stop
MDW
BOS
2h 15m
nonstop
Depart: Fri Mar 3 2017 Return: Sun Mar 5 2017 Trip spans 3 days
American Airlines
American Airlines
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 13m
nonstop
Depart: Sun Jan 22 2017 Return: Fri Jan 27 2017 Trip spans 6 days
Delta
Delta
BOS
MDW
4h 31m
1 stop
MDW
BOS
5h 39m
1 stop
Depart: Wed Feb 1 2017 Return: Sun Feb 5 2017 Trip spans 5 days
Major Airline
Major Airline
BOS
ORD
3h 00m
nonstop
ORD
BOS
2h 11m
nonstop
Depart: Tue Jan 31 2017 Return: Wed Feb 1 2017 Trip spans 2 days
JetBlue
JetBlue
BOS
ORD
3h 00m
nonstop
ORD
BOS
2h 15m
nonstop
Depart: Tue Feb 7 2017 Return: Tue Feb 14 2017 Trip spans 8 days
Major Airline
Major Airline
BOS
ORD
2h 59m
nonstop
ORD
BOS
2h 10m
nonstop
Depart: Wed May 31 2017 Return: Wed Jun 7 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 28m
nonstop
Depart: Sat Jun 3 2017 Return: Wed Jun 7 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 28m
nonstop
Depart: Fri Jan 27 2017 Return: Sat Jan 28 2017 Trip spans 2 days
Major Airline
Major Airline
BOS
ORD
2h 58m
nonstop
ORD
BOS
2h 11m
nonstop
Depart: Wed Jul 19 2017 Return: Wed Aug 9 2017 Trip spans 22 days
JetBlue
JetBlue
BOS
ORD
2h 49m
nonstop
ORD
BOS
2h 19m
nonstop
Depart: Tue May 2 2017 Return: Thu May 4 2017 Trip spans 3 days
Major Airline
Major Airline
BOS
ORD
2h 57m
nonstop
ORD
BOS
2h 19m
nonstop
Depart: Sat Feb 11 2017 Return: Thu Feb 16 2017 Trip spans 6 days
Southwest
Southwest
BOS
MDW
2h 50m
nonstop
MDW
BOS
2h 15m
nonstop
Depart: Wed Mar 22 2017 Return: Sat Mar 25 2017 Trip spans 4 days
Major Airline
Major Airline
BOS
ORD
2h 53m
nonstop
ORD
BOS
2h 13m
nonstop
Depart: Mon Apr 3 2017 Return: Thu Apr 6 2017 Trip spans 4 days
Major Airline
Major Airline
BOS
ORD
3h 02m
nonstop
ORD
BOS
2h 16m
nonstop
Depart: Sat Jul 1 2017 Return: Wed Jul 5 2017 Trip spans 5 days
American Airlines
American Airlines
BOS
ORD
2h 39m
nonstop
ORD
BOS
2h 21m
nonstop
Depart: Sat Jan 28 2017 Return: Tue Jan 31 2017 Trip spans 4 days
Delta
Delta
BOS
MDW
4h 38m
1 stop
MDW
BOS
3h 44m
1 stop
Depart: Fri Jun 2 2017 Return: Sat Jun 3 2017 Trip spans 2 days
Major Airline
Major Airline
BOS
ORD
2h 44m
nonstop
ORD
BOS
2h 18m
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 Jan 12 - Mar 11
2253 10:15 am 12:14 pm Jan 14 - Feb 11
2253 10:15 am 12:14 pm Jan 12 - Feb 15
2253 10:20 am 12:19 pm Feb 16 - Mar 10
2253 10:35 am 12:34 pm Feb 18 - Mar 11
1240 12:00 pm 2:01 pm Feb 16 - Mar 10
1240 12:00 pm 2:01 pm Jan 12 - Feb 15
252 1:55 pm 3:54 pm Feb 20 - Feb 20
252 1:55 pm 3:54 pm Feb 13 - Feb 17
252 1:55 pm 3:54 pm Feb 12 - Mar 5
252 1:55 pm 3:54 pm Feb 2 - Feb 10
252 1:55 pm 3:54 pm Jan 12 - Jan 26
252 1:55 pm 3:54 pm Jan 31 - Feb 28
252 1:55 pm 3:54 pm Jan 22 - Jan 22
252 1:55 pm 3:54 pm Jan 29 - Jan 29
252 1:55 pm 3:54 pm Jan 23 - Jan 30
252 2:01 pm 4:02 pm Jan 14 - Feb 11
252 2:05 pm 4:06 pm Feb 18 - Mar 11
197 3:45 pm 5:43 pm Jan 12 - Mar 10
1530 5:15 pm 7:18 pm Feb 17 - Mar 3
1530 5:15 pm 7:18 pm Feb 16 - Feb 28
1530 5:20 pm 7:23 pm Jan 13 - Jan 27
1530 5:20 pm 7:23 pm Jan 12 - Jan 26
1530 5:20 pm 7:23 pm Jan 29 - Feb 15
1530 5:20 pm 7:23 pm Jan 28 - Feb 14
40 7:06 pm 9:05 pm Feb 16 - Mar 10
40 7:11 pm 9:10 pm Jan 12 - Feb 15
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Boston
$95
Destination

Chicago
only $95
only $116
Airlines Airline reviews

153 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 5.6.

Overall
5.8
Boarding
6.1
Crew
6.7
Comfort
5.5
Food
4.2
Entertainment
4.3