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.
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 Chicago to Boston Logan International

(Round-trip)
Depart: Wed Sep 6 2017 Return: Tue Sep 12 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Fri Sep 29 2017 Return: Mon Oct 2 2017 Trip spans 4 days
United
United
ORD
BOS
2h 19m
nonstop
BOS
ORD
2h 45m
nonstop
Depart: Sat Dec 2 2017 Return: Sat Dec 9 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
BOS
2h 12m
nonstop
BOS
ORD
3h 07m
nonstop
Depart: Sat Sep 2 2017 Return: Wed Sep 6 2017 Trip spans 5 days
Delta
Delta
MDW
BOS
6h 17m
1 stop
BOS
MDW
7h 10m
1 stop
Depart: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Tue Oct 3 2017 Return: Wed Oct 11 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Wed Jan 17 2018 Return: Thu Jan 25 2018 Trip spans 9 days
American Airlines
American Airlines
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 49m
nonstop
Depart: Fri Feb 2 2018 Return: Tue Feb 6 2018 Trip spans 5 days
United
United
ORD
BOS
2h 22m
nonstop
BOS
ORD
3h 00m
nonstop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 47m
nonstop
Depart: Sun Feb 11 2018 Return: Wed Feb 14 2018 Trip spans 4 days
American Airlines
American Airlines
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 46m
nonstop
Depart: Fri Dec 8 2017 Return: Mon Dec 11 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
BOS
2h 10m
nonstop
BOS
ORD
3h 05m
nonstop
Depart: Fri Oct 27 2017 Return: Mon Oct 30 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Fri Dec 1 2017 Return: Mon Dec 4 2017 Trip spans 4 days
United
United
ORD
BOS
2h 22m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Fri Sep 8 2017 Return: Mon Sep 11 2017 Trip spans 4 days
Delta
Delta
MDW
BOS
5h 40m
1 stop
BOS
MDW
4h 51m
1 stop
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Delta
Delta
MDW
BOS
3h 58m
1 stop
BOS
MDW
5h 42m
1 stop
Depart: Thu Aug 31 2017 Return: Sun Sep 3 2017 Trip spans 4 days
United
United
ORD
BOS
2h 17m
nonstop
BOS
ORD
2h 49m
nonstop
Depart: Fri Oct 20 2017 Return: Mon Oct 23 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Sat Oct 7 2017 Return: Sun Oct 15 2017 Trip spans 9 days
Delta
Delta
MDW
BOS
7h 47m
1 stop
BOS
MDW
5h 47m
1 stop
Depart: Thu Aug 31 2017 Return: Tue Sep 5 2017 Trip spans 6 days
United
United
ORD
BOS
2h 17m
nonstop
BOS
ORD
2h 46m
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 9:16 am Aug 23 - Sep 5
256 6:00 am 9:16 am Sep 7 - Oct 6
1240 7:14 am 10:32 am Sep 4 - Sep 11
1240 7:14 am 10:32 am Sep 3 - Sep 9
1240 7:14 am 10:32 am Aug 26 - Sep 2
1240 7:14 am 10:32 am Aug 22 - Sep 1
1240 7:14 am 10:32 am Sep 16 - Sep 30
1240 7:14 am 10:32 am Sep 13 - Sep 25
1240 7:14 am 10:32 am Sep 12 - Sep 12
2586 8:50 am 12:07 pm Aug 16 - Aug 25
2586 8:50 am 12:07 pm Aug 26 - Nov 4
1257 10:10 am 1:27 pm Aug 22 - Oct 4
1466 11:50 am 3:05 pm Aug 22 - Sep 1
1466 11:50 am 3:05 pm Sep 3 - Oct 2
1466 11:50 am 3:05 pm Sep 2 - Sep 2
2626 1:20 pm 4:38 pm Aug 22 - Sep 1
2626 1:20 pm 4:38 pm Sep 4 - Sep 5
2626 1:20 pm 4:38 pm Sep 6 - Oct 6
2387 3:00 pm 6:18 pm Aug 22 - Sep 1
2387 3:00 pm 6:18 pm Aug 26 - Sep 2
2387 3:00 pm 6:18 pm Sep 3 - Sep 9
2387 3:00 pm 6:18 pm Sep 4 - Oct 4
2387 3:00 pm 6:18 pm Sep 16 - Sep 30
1205 4:40 pm 7:59 pm Aug 22 - Sep 8
1205 4:40 pm 7:59 pm Aug 27 - Aug 27
1205 4:40 pm 7:59 pm Sep 3 - Sep 24
1205 4:40 pm 7:59 pm Sep 9 - Sep 30
1205 4:40 pm 7:59 pm Sep 11 - Sep 18
1205 4:40 pm 7:59 pm Sep 12 - Sep 12
1205 4:40 pm 7:59 pm Sep 19 - Sep 25
1320 6:35 pm 9:55 pm Aug 22 - Sep 8
1320 6:35 pm 9:55 pm Sep 9 - Oct 6
1320 7:31 pm 10:48 pm Aug 26 - Sep 2
2740 8:10 pm 11:28 pm Aug 22 - Sep 5
2740 8:10 pm 11:28 pm Aug 23 - Sep 1
2740 8:10 pm 11:28 pm Sep 4 - Oct 9
1569 9:42 pm 12:58 am Aug 22 - Sep 5
1569 9:42 pm 12:58 am Aug 23 - Sep 1
1569 9:42 pm 12:58 am Sep 4 - Oct 9
1569 9:42 pm 12:58 am Sep 6 - Oct 4
1569 9:42 pm 12:58 am Sep 12 - Oct 3
* 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.

Airports
Origin

Chicago
only $89
only $164
Destination

Boston
$89
Airlines Airline reviews

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

Overall
6.2
Boarding
6.4
Crew
6.8
Comfort
6.1
Food
4.9
Entertainment
5.0