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
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: Tue May 17 2016 Return: Wed Jun 1 2016 Trip spans 16 days
United
United
ORD
BOS
2h 20m
nonstop
BOS
ORD
2h 52m
nonstop
Depart: Sat May 14 2016 Return: Tue May 17 2016 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 23m
nonstop
BOS
ORD
2h 51m
nonstop
Depart: Sat May 7 2016 Return: Sat May 14 2016 Trip spans 8 days
Southwest
Southwest
MDW
BOS
2h 10m
nonstop
BOS
MDW
2h 45m
nonstop
Depart: Tue Jun 14 2016 Return: Wed Jun 15 2016 Trip spans 2 days
Major Airline
Major Airline
ORD
BOS
2h 32m
nonstop
BOS
ORD
2h 45m
nonstop
Depart: Wed May 11 2016 Return: Fri May 13 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 23m
nonstop
BOS
ORD
2h 51m
nonstop
Depart: Mon Aug 1 2016 Return: Tue Aug 16 2016 Trip spans 16 days
Delta
Delta
MDW
BOS
5h 37m
1 stop
BOS
MDW
6h 13m
1 stop
Depart: Thu Sep 1 2016 Return: Sun Sep 4 2016 Trip spans 4 days
Major Airline
Major Airline
ORD
BOS
2h 21m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Thu May 5 2016 Return: Sun May 8 2016 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 23m
nonstop
BOS
ORD
2h 51m
nonstop
Depart: Sat Oct 1 2016 Return: Sat Oct 15 2016 Trip spans 15 days
Major Airline
Major Airline
ORD
BOS
2h 14m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Tue May 3 2016 Return: Thu May 5 2016 Trip spans 3 days
Southwest
Southwest
MDW
BOS
2h 10m
nonstop
BOS
MDW
2h 40m
nonstop
Depart: Wed Jun 22 2016 Return: Tue Jun 28 2016 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 52m
nonstop
Depart: Sat Oct 29 2016 Return: Sun Oct 30 2016 Trip spans 2 days
Major Airline
Major Airline
ORD
BOS
2h 30m
nonstop
BOS
ORD
2h 44m
nonstop
Depart: Sat Jun 25 2016 Return: Wed Jul 6 2016 Trip spans 12 days
Southwest
Southwest
MDW
BOS
2h 10m
nonstop
BOS
MDW
5h 30m
1 stop
Depart: Wed Jul 13 2016 Return: Wed Jul 20 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 52m
nonstop
Depart: Tue Jul 19 2016 Return: Wed Jul 27 2016 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 52m
nonstop
Depart: Tue Aug 16 2016 Return: Tue Aug 23 2016 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 52m
nonstop
Depart: Fri Jun 10 2016 Return: Sun Jun 12 2016 Trip spans 3 days
Southwest
Southwest
MDW
BOS
2h 10m
nonstop
BOS
MDW
4h 40m
1 stop
Depart: Tue Aug 2 2016 Return: Tue Aug 9 2016 Trip spans 8 days
Delta
Delta
MDW
BOS
4h 47m
1 stop
BOS
MDW
6h 13m
1 stop
Depart: Wed Aug 24 2016 Return: Sat Aug 27 2016 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 24m
nonstop
BOS
ORD
2h 52m
nonstop
Depart: Fri Sep 30 2016 Return: Sun Oct 2 2016 Trip spans 3 days
Spirit Airlines
Spirit Airlines
ORD
BOS
2h 23m
nonstop
BOS
ORD
2h 52m
nonstop
Direct flights CHI to BOS on American Airlines
Flight # Depart ORD Arrive BOS Sun Mon Tue Wed Thu Fri Sat Valid Between
1183 6:00 am 9:10 am May 7 - May 28
1183 6:00 am 9:11 am Jun 4 - Jun 4
1183 6:00 am 9:11 am Jun 2 - Jun 9
1183 6:00 am 9:10 am May 5 - Jun 1
1240 7:00 am 10:14 am Jun 2 - Jun 3
1240 7:00 am 10:14 am Jun 6 - Jun 30
1240 7:00 am 10:14 am Jun 4 - Jun 25
1240 7:00 am 10:12 am May 5 - Jun 1
2607 7:00 am 10:14 am Jun 5 - Jun 26
1299 8:25 am 11:35 am May 7 - May 28
1299 8:25 am 11:35 am May 5 - Jun 1
1257 8:30 am 11:46 am Jun 2 - Jul 4
252 10:05 am 1:20 pm May 5 - Jun 1
252 10:05 am 1:20 pm May 7 - May 28
252 10:05 am 1:21 pm Jun 2 - Jun 30
2224 11:49 am 3:05 pm Jun 2 - Aug 22
197 11:50 am 3:06 pm May 5 - Jun 1
197 12:05 pm 3:26 pm Jun 4 - Aug 20
197 12:05 pm 3:25 pm May 7 - May 28
1503 1:20 pm 4:38 pm Jun 7 - Aug 4
1503 1:20 pm 4:38 pm Jun 2 - Jun 2
1503 1:20 pm 4:38 pm Jun 3 - Jun 10
1503 1:24 pm 4:42 pm Jun 4 - Jun 25
1503 1:25 pm 4:40 pm May 5 - Jun 1
1503 1:25 pm 4:40 pm May 7 - May 28
8864 1:35 pm 5:05 pm Jun 2 - Jun 2
2387 3:00 pm 6:15 pm May 5 - May 31
2387 3:00 pm 6:15 pm Jun 1 - Jun 1
2387 3:05 pm 6:25 pm Jun 7 - Jun 7
2387 3:05 pm 6:25 pm Jun 2 - Jun 2
2387 3:05 pm 6:25 pm Jun 6 - Jun 13
2387 3:05 pm 6:25 pm Jun 4 - Jun 4
2387 3:05 pm 6:25 pm Jun 5 - Jun 5
2387 3:05 pm 6:25 pm Jun 3 - Jun 3
366 3:40 pm 6:57 pm May 26 - May 26
1205 4:55 pm 8:16 pm Jun 5 - Jul 4
1205 4:55 pm 8:16 pm Jun 2 - Jun 4
1205 5:10 pm 8:26 pm May 27 - Jun 1
1205 5:10 pm 8:26 pm May 5 - May 25
1205 5:10 pm 8:26 pm May 26 - May 26
1205 5:10 pm 8:26 pm May 7 - May 28
366 6:36 pm 9:59 pm Jun 2 - Jul 1
366 6:41 pm 9:59 pm May 17 - May 25
366 6:41 pm 9:59 pm May 12 - May 12
366 6:41 pm 9:59 pm May 10 - May 10
366 6:41 pm 9:59 pm May 6 - May 16
366 6:41 pm 9:59 pm May 27 - Jun 1
2326 8:25 pm 11:43 pm Jun 2 - Jun 8
1167 9:44 pm 12:59 am Jun 2 - Jul 1
1167 9:49 pm 12:59 am May 27 - Jun 1
1167 9:49 pm 12:59 am May 26 - May 26
1167 9:49 pm 12:59 am May 5 - May 25
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We make every attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set 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 don'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 $79
only $111
Destination

Boston
$79