Find Deals on 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
Students
under 26
The price shown for each flight will be the average for all passengers including any infants.
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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 Oct 5 2016 Return: Wed Oct 12 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 26m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Wed Oct 12 2016 Return: Tue Oct 18 2016 Trip spans 7 days
Major Airline
Major Airline
ORD
BOS
2h 26m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Sat Dec 3 2016 Return: Wed Dec 7 2016 Trip spans 5 days
JetBlue
JetBlue
ORD
BOS
2h 11m
nonstop
BOS
ORD
2h 57m
nonstop
Depart: Sat Oct 29 2016 Return: Wed Nov 2 2016 Trip spans 5 days
Southwest
Southwest
MDW
BOS
2h 10m
nonstop
BOS
MDW
2h 45m
nonstop
Depart: Tue Oct 25 2016 Return: Wed Oct 26 2016 Trip spans 2 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 26m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Wed Nov 2 2016 Return: Mon Nov 7 2016 Trip spans 6 days
Major Airline
Major Airline
ORD
BOS
2h 11m
nonstop
BOS
ORD
2h 57m
nonstop
Depart: Wed Nov 2 2016 Return: Tue Nov 8 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 26m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Tue Nov 1 2016 Return: Wed Nov 2 2016 Trip spans 2 days
Major Airline
Major Airline
ORD
BOS
2h 14m
nonstop
BOS
ORD
2h 50m
nonstop
Depart: Wed Mar 8 2017 Return: Wed Mar 15 2017 Trip spans 7 days
JetBlue
JetBlue
ORD
BOS
2h 14m
nonstop
BOS
ORD
3h 00m
nonstop
Depart: Thu Nov 10 2016 Return: Sat Nov 12 2016 Trip spans 3 days
Delta
Delta
MDW
BOS
3h 53m
1 stop
BOS
MDW
4h 23m
1 stop
Depart: Thu Nov 10 2016 Return: Sun Nov 13 2016 Trip spans 4 days
Major Airline
Major Airline
ORD
BOS
2h 11m
nonstop
BOS
ORD
2h 57m
nonstop
Depart: Wed Jan 4 2017 Return: Sat Jan 7 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
BOS
2h 14m
nonstop
BOS
ORD
3h 02m
nonstop
Depart: Sat Mar 4 2017 Return: Sat Mar 11 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
BOS
2h 14m
nonstop
BOS
ORD
2h 58m
nonstop
Depart: Thu Jan 12 2017 Return: Sun Jan 15 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
BOS
2h 14m
nonstop
BOS
ORD
3h 01m
nonstop
Depart: Fri Sep 30 2016 Return: Sun Oct 2 2016 Trip spans 3 days
United
United
ORD
BOS
2h 22m
nonstop
BOS
ORD
2h 46m
nonstop
Depart: Thu Feb 2 2017 Return: Sun Feb 5 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
BOS
2h 22m
nonstop
BOS
ORD
3h 01m
nonstop
Depart: Thu Mar 2 2017 Return: Sun Mar 5 2017 Trip spans 4 days
JetBlue
JetBlue
ORD
BOS
2h 15m
nonstop
BOS
ORD
2h 58m
nonstop
Depart: Mon Feb 13 2017 Return: Wed Feb 15 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
BOS
2h 14m
nonstop
BOS
ORD
2h 57m
nonstop
Depart: Tue Oct 4 2016 Return: Wed Oct 5 2016 Trip spans 2 days
Major Airline
Major Airline
MDW
BOS
2h 10m
nonstop
BOS
MDW
2h 45m
nonstop
Depart: Wed Feb 22 2017 Return: Sat Feb 25 2017 Trip spans 4 days
Delta
Delta
MDW
BOS
3h 49m
1 stop
BOS
MDW
6h 04m
1 stop
Direct flights CHI to BOS on American Airlines
Flight # Depart ORD Arrive BOS Sun Mon Tue Wed Thu Fri Sat Valid Between
1183 6:05 am 9:18 am Oct 6 - Oct 28
1183 6:05 am 9:18 am Oct 9 - Oct 30
1183 6:05 am 9:18 am Nov 3 - Nov 3
1183 6:05 am 9:13 am Nov 4 - Nov 4
1183 6:05 am 9:13 am Nov 6 - Nov 20
1240 7:05 am 10:14 am Nov 4 - Nov 4
1240 7:05 am 10:22 am Sep 29 - Oct 28
1240 7:05 am 10:14 am Nov 5 - Nov 5
1240 7:05 am 10:22 am Oct 31 - Oct 31
1240 7:05 am 10:22 am Nov 1 - Nov 3
1240 7:05 am 10:14 am Nov 6 - Nov 23
2607 7:05 am 10:22 am Oct 2 - Oct 30
1183 7:10 am 10:28 am Oct 8 - Oct 29
252 8:24 am 11:33 am Nov 4 - Nov 4
252 8:25 am 11:34 am Nov 5 - Nov 5
1257 8:35 am 11:53 am Sep 29 - Nov 3
252 8:40 am 11:51 am Nov 6 - Nov 22
1257 9:57 am 1:05 pm Nov 4 - Nov 4
1257 10:05 am 1:16 pm Nov 5 - Nov 5
252 10:05 am 1:21 pm Sep 29 - Oct 22
252 10:05 am 1:21 pm Oct 23 - Oct 30
252 10:05 am 1:21 pm Oct 31 - Oct 31
252 10:05 am 1:21 pm Nov 1 - Nov 3
1257 10:10 am 1:21 pm Nov 6 - Nov 23
2224 11:50 am 3:12 pm Sep 29 - Oct 28
2224 11:50 am 3:12 pm Oct 30 - Nov 3
2224 12:00 pm 3:11 pm Nov 6 - Nov 23
2224 12:00 pm 3:11 pm Nov 4 - Nov 5
197 12:05 pm 3:28 pm Oct 1 - Oct 29
1503 1:20 pm 4:41 pm Oct 18 - Nov 3
1503 1:20 pm 4:41 pm Nov 2 - Nov 2
1503 1:20 pm 4:41 pm Oct 19 - Oct 30
1503 1:20 pm 4:41 pm Sep 30 - Oct 17
1503 1:20 pm 4:41 pm Sep 29 - Oct 13
1503 1:20 pm 4:30 pm Nov 6 - Nov 23
1503 1:20 pm 4:30 pm Nov 5 - Nov 5
1503 1:20 pm 4:30 pm Nov 4 - Nov 4
1503 1:21 pm 4:42 pm Oct 29 - Oct 29
1503 1:21 pm 4:42 pm Oct 1 - Oct 22
2387 3:05 pm 6:26 pm Oct 31 - Nov 3
2387 3:05 pm 6:26 pm Oct 10 - Oct 21
2387 3:05 pm 6:26 pm Oct 24 - Oct 28
2387 3:05 pm 6:26 pm Sep 29 - Oct 7
2387 3:05 pm 6:26 pm Oct 1 - Oct 29
2387 3:08 pm 6:18 pm Nov 6 - Nov 27
2387 3:08 pm 6:18 pm Nov 4 - Nov 4
2387 3:19 pm 6:40 pm Oct 9 - Oct 9
2387 3:19 pm 6:40 pm Oct 30 - Oct 30
2387 3:19 pm 6:40 pm Oct 23 - Oct 23
1205 4:44 pm 7:54 pm Nov 4 - Nov 4
1205 4:44 pm 8:02 pm Oct 31 - Oct 31
1205 4:44 pm 8:02 pm Oct 30 - Oct 30
1205 4:44 pm 7:54 pm Nov 6 - Nov 20
1205 4:44 pm 8:02 pm Oct 29 - Oct 29
1205 4:44 pm 8:02 pm Sep 29 - Oct 28
1205 4:44 pm 8:02 pm Oct 1 - Oct 8
1205 4:44 pm 8:02 pm Oct 9 - Oct 23
1205 4:44 pm 8:02 pm Nov 1 - Nov 3
2387 4:44 pm 7:54 pm Nov 5 - Nov 5
366 6:35 pm 9:56 pm Oct 6 - Oct 13
366 6:35 pm 9:48 pm Nov 5 - Nov 5
366 6:35 pm 9:48 pm Nov 4 - Nov 4
366 6:35 pm 9:56 pm Oct 18 - Oct 27
366 6:35 pm 9:56 pm Oct 30 - Nov 2
366 6:35 pm 9:48 pm Nov 6 - Dec 14
366 6:35 pm 9:56 pm Oct 19 - Oct 29
366 6:35 pm 9:56 pm Oct 7 - Oct 17
366 6:35 pm 9:56 pm Nov 1 - Nov 3
1167 8:30 pm 11:40 pm Nov 6 - Dec 11
1167 8:30 pm 11:40 pm Nov 4 - Nov 4
1167 8:30 pm 11:49 pm Oct 10 - Oct 21
1167 8:30 pm 11:49 pm Sep 29 - Oct 7
1167 8:30 pm 11:49 pm Oct 9 - Oct 16
1167 8:30 pm 11:49 pm Oct 23 - Oct 23
1167 8:30 pm 11:49 pm Oct 24 - Oct 28
1167 8:30 pm 11:49 pm Nov 1 - Nov 3
1167 8:30 pm 11:49 pm Oct 30 - Oct 30
* 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 $80
only $103
Destination

Boston
$80
Airlines Airline reviews

190 travelers who booked a flight from Chicago to Boston rated their chosen airlines with an average of 5.8.

Overall
6.0
Boarding
6.1
Crew
6.6
Comfort
5.7
Food
4.6
Entertainment
4.4