Find Cheap Flights from Chicago to Boston Logan International (CHI - BOS)

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 Chicago to Boston Logan International

(Round-trip)
Depart: Tue Jun 13 2017 Return: Wed Jun 14 2017 Trip spans 2 days
United
United
ORD
BOS
2h 20m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Wed Aug 23 2017 Return: Sat Aug 26 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 47m
nonstop
Depart: Tue Sep 5 2017 Return: Thu Sep 7 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 47m
nonstop
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
BOS
2h 27m
nonstop
BOS
ORD
2h 43m
nonstop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Southwest
Southwest
MDW
BOS
2h 15m
nonstop
BOS
MDW
2h 50m
nonstop
Depart: Tue Jun 6 2017 Return: Wed Jun 7 2017 Trip spans 2 days
Delta
Delta
MDW
BOS
6h 07m
1 stop
BOS
MDW
4h 16m
1 stop
Depart: Fri Jun 16 2017 Return: Tue Jun 20 2017 Trip spans 5 days
United
United
ORD
BOS
2h 22m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 46m
nonstop
Depart: Mon Oct 2 2017 Return: Tue Oct 3 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 33m
nonstop
Depart: Wed Jun 7 2017 Return: Wed Jun 14 2017 Trip spans 8 days
United
United
ORD
BOS
2h 17m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Sat Aug 26 2017 Return: Sat Sep 2 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 47m
nonstop
Depart: Tue Sep 5 2017 Return: Sun Sep 10 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 46m
nonstop
Depart: Wed Jul 19 2017 Return: Wed Jul 26 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 55m
nonstop
Depart: Tue Aug 15 2017 Return: Tue Aug 22 2017 Trip spans 8 days
Delta
Delta
MDW
BOS
6h 35m
1 stop
BOS
MDW
6h 33m
1 stop
Depart: Sun Oct 1 2017 Return: Sun Oct 8 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
BOS
2h 20m
nonstop
BOS
ORD
2h 53m
nonstop
Depart: Fri Jun 16 2017 Return: Mon Jul 24 2017 Trip spans 39 days
United
United
ORD
BOS
2h 22m
nonstop
BOS
ORD
2h 48m
nonstop
Depart: Wed Aug 30 2017 Return: Sun Sep 3 2017 Trip spans 5 days
Delta
Delta
MDW
BOS
4h 01m
1 stop
BOS
MDW
7h 24m
1 stop
Depart: Sat Aug 12 2017 Return: Sat Aug 19 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 47m
nonstop
Depart: Sat Aug 12 2017 Return: Tue Aug 22 2017 Trip spans 11 days
American Airlines
American Airlines
ORD
BOS
2h 18m
nonstop
BOS
ORD
2h 47m
nonstop
Depart: Sat Oct 14 2017 Return: Sat Oct 21 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
BOS
2h 17m
nonstop
BOS
ORD
2h 53m
nonstop
Direct flights CHI to BOS on American Airlines
Flight # Depart ORD Arrive BOS Sun Mon Tue Wed Thu Fri Sat Valid Between
256 6:00 am 9:18 am Jun 2 - Jun 30
1240 7:14 am 10:35 am Jun 18 - Jul 30
1240 7:14 am 10:35 am Jun 16 - Aug 3
1240 7:14 am 10:35 am Jun 3 - Jul 29
1240 7:14 am 10:35 am Jun 4 - Jun 11
1240 7:14 am 10:35 am Jun 2 - Jun 15
2586 8:50 am 12:09 pm Jun 2 - Aug 3
2586 8:50 am 12:09 pm Jun 3 - Jul 1
1257 9:55 am 1:16 pm Jun 2 - Aug 3
2224 11:54 am 3:13 pm Jun 2 - Aug 3
2626 1:20 pm 4:44 pm Jun 2 - Aug 3
2626 1:25 pm 4:50 pm Jun 10 - Jul 29
2626 1:25 pm 4:50 pm Jun 3 - Jun 3
2387 3:05 pm 6:29 pm Jun 2 - Jun 12
2387 3:05 pm 6:29 pm Jun 6 - Jun 6
2387 3:05 pm 6:29 pm Jun 13 - Jun 30
1205 4:44 pm 8:08 pm Jun 2 - Jun 30
1205 4:44 pm 8:08 pm Jul 3 - Jul 3
2387 4:50 pm 8:14 pm Jun 3 - Jul 29
1320 6:40 pm 10:06 pm Jun 2 - Aug 3
1320 6:40 pm 10:06 pm Jun 3 - Jul 29
1320 6:40 pm 10:06 pm Jun 4 - Jul 30
2194 8:05 pm 11:24 pm Jun 4 - Jul 2
2740 8:05 pm 11:24 pm Jun 2 - Jun 30
2740 8:05 pm 11:24 pm Jun 6 - Jun 27
1569 9:44 pm 1:04 am Jun 2 - Jun 28
1569 9:44 pm 1:04 am Jun 6 - Jun 27
1569 9:44 pm 1:04 am Jun 29 - Jul 3
* 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.

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Airports
Origin

Chicago
only $119
only $169
Destination

Boston
$119
Airlines Airline reviews

310 travelers who booked a flight from Chicago to Boston rated their chosen airlines with an average of 6.3.

Overall
6.5
Boarding
6.6
Crew
7.0
Comfort
6.3
Food
5.1
Entertainment
5.2