Find Deals on Flights from Boston Logan International to Chicago Midway (BOS - MDW)

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 Midway

(Round-trip)
Depart: Mon Dec 12 2016 Return: Sat Dec 17 2016 Trip spans 6 days
Major Airline
Major Airline
BOS
12:00a
MDW
2:42a
2h 42m
nonstop
MDW
8:00a
BOS
8:42a
0h 42m
nonstop
Depart: Tue Dec 13 2016 Return: Tue Dec 20 2016 Trip spans 8 days
Delta
Delta
BOS
4:05a
MDW
8:19a
4h 14m
1 stop
MDW
10:16a
BOS
3:32p
5h 16m
1 stop
Depart: Wed Dec 14 2016 Return: Fri Dec 16 2016 Trip spans 3 days
Delta
Delta
BOS
4:05a
MDW
8:19a
4h 14m
1 stop
MDW
8:59a
BOS
2:38p
5h 39m
1 stop
Depart: Thu Dec 15 2016 Return: Sat Dec 17 2016 Trip spans 3 days
Delta
Delta
BOS
2:09a
MDW
7:43a
5h 34m
1 stop
MDW
12:59p
BOS
6:32p
5h 33m
1 stop
Depart: Fri Dec 16 2016 Return: Sun Dec 18 2016 Trip spans 3 days
Delta
Delta
BOS
1:00a
MDW
7:45a
6h 45m
1 stop
MDW
1:00a
BOS
8:10a
7h 10m
1 stop
Depart: Sun Dec 18 2016 Return: Mon Dec 19 2016 Trip spans 2 days
Delta
Delta
BOS
12:35a
MDW
4:53a
4h 18m
1 stop
MDW
11:45a
BOS
4:19p
4h 34m
1 stop
Depart: Mon Dec 19 2016 Return: Tue Dec 20 2016 Trip spans 2 days
Delta
Delta
BOS
4:00a
MDW
10:53a
6h 53m
1 stop
MDW
7:47a
BOS
12:02p
4h 15m
1 stop
Depart: Wed Jan 4 2017 Return: Sat Jan 7 2017 Trip spans 4 days
Delta
Delta
BOS
6:32a
MDW
3:20p
8h 48m
1 stop
MDW
12:11p
BOS
5:56p
5h 45m
1 stop
Depart: Thu Jan 5 2017 Return: Sat Jan 7 2017 Trip spans 3 days
Delta
Delta
BOS
9:29a
MDW
3:20p
5h 51m
1 stop
MDW
12:11p
BOS
5:56p
5h 45m
1 stop
Depart: Fri Jan 6 2017 Return: Sat Jan 7 2017 Trip spans 2 days
Delta
Delta
BOS
1:50a
MDW
8:22a
6h 32m
1 stop
MDW
12:11p
BOS
5:56p
5h 45m
1 stop
Depart: Sat Jan 7 2017 Return: Sun Jan 8 2017 Trip spans 2 days
Delta
Delta
BOS
12:30a
MDW
5:31a
5h 01m
1 stop
MDW
7:25a
BOS
1:46p
6h 21m
1 stop
Depart: Sun Jan 8 2017 Return: Mon Jan 9 2017 Trip spans 2 days
Delta
Delta
BOS
6:55a
MDW
3:05p
8h 10m
1 stop
MDW
2:10a
BOS
8:04a
5h 54m
1 stop
Depart: Mon Jan 9 2017 Return: Tue Jan 10 2017 Trip spans 2 days
Delta
Delta
BOS
9:34a
MDW
2:05p
4h 31m
1 stop
MDW
4:15a
BOS
7:59a
3h 44m
1 stop
Depart: Tue Jan 10 2017 Return: Mon Jan 16 2017 Trip spans 7 days
Delta
Delta
BOS
9:27a
MDW
6:09p
8h 42m
1 stop
MDW
12:26p
BOS
5:59p
5h 33m
1 stop
Depart: Wed Jan 11 2017 Return: Fri Jan 13 2017 Trip spans 3 days
Delta
Delta
BOS
3:40a
MDW
8:34a
4h 54m
1 stop
MDW
1:45a
BOS
5:58a
4h 13m
1 stop
Depart: Thu Jan 12 2017 Return: Mon Jan 16 2017 Trip spans 5 days
Delta
Delta
BOS
9:34a
MDW
5:00p
7h 26m
1 stop
MDW
12:26p
BOS
5:59p
5h 33m
1 stop
Depart: Fri Jan 13 2017 Return: Sat Jan 14 2017 Trip spans 2 days
Delta
Delta
BOS
3:40a
MDW
8:34a
4h 54m
1 stop
MDW
12:11p
BOS
5:56p
5h 45m
1 stop
Depart: Sat Jan 14 2017 Return: Mon Jan 16 2017 Trip spans 3 days
Delta
Delta
BOS
2:00a
MDW
11:01a
9h 01m
1 stop
MDW
10:29a
BOS
5:59p
7h 30m
1 stop
Depart: Mon Jan 16 2017 Return: Tue Jan 17 2017 Trip spans 2 days
Delta
Delta
BOS
3:40a
MDW
8:34a
4h 54m
1 stop
MDW
1:45a
BOS
5:58a
4h 13m
1 stop
Depart: Tue Jan 17 2017 Return: Sat Jan 21 2017 Trip spans 5 days
Delta
Delta
BOS
4:45a
MDW
11:03a
6h 18m
1 stop
MDW
11:50a
BOS
4:01p
4h 11m
1 stop
Select an airline:  Southwest
Direct flights BOS to MDW on Southwest
Flight # Depart BOS Arrive MDW Sun Mon Tue Wed Thu Fri Sat Valid Between
746 5:05 am 6:55 am Dec 21 - Jan 2
2112 5:20 am 7:10 am Dec 24 - Dec 24
4556 5:25 am 7:20 am Dec 1 - Dec 14
4556 5:25 am 7:20 am Jan 4 - Jan 4
1347 5:30 am 7:25 am Dec 4 - Dec 11
2201 5:30 am 7:25 am Dec 17 - Dec 17
2201 5:30 am 7:25 am Dec 15 - Dec 16
2576 5:30 am 7:25 am Jan 1 - Jan 3
4556 5:30 am 7:25 am Dec 18 - Dec 20
4954 5:35 am 7:25 am Jan 7 - Mar 4
1621 5:50 am 7:45 am Jan 5 - Feb 13
5545 6:00 am 7:50 am Dec 31 - Dec 31
2497 6:20 am 8:15 am Jan 8 - Jan 29
4743 6:40 am 8:35 am Dec 21 - Jan 2
2641 8:15 am 10:10 am Jan 7 - Mar 4
528 8:25 am 10:20 am Dec 24 - Dec 24
2252 8:55 am 10:50 am Dec 25 - Dec 25
621 8:55 am 10:50 am Jan 1 - Jan 1
621 8:55 am 10:50 am Dec 4 - Dec 18
668 8:55 am 10:50 am Dec 1 - Dec 14
668 8:55 am 10:50 am Dec 15 - Dec 16
668 8:55 am 10:50 am Dec 19 - Dec 20
668 8:55 am 10:50 am Jan 3 - Jan 3
668 8:55 am 10:50 am Jan 4 - Jan 4
6266 9:00 am 10:55 am Dec 21 - Jan 2
3451 9:30 am 11:25 am Dec 17 - Dec 17
6682 9:45 am 11:40 am Dec 31 - Dec 31
428 11:15 am 1:05 pm Jan 5 - Jan 5
428 11:15 am 1:05 pm Jan 6 - Jan 13
3435 11:25 am 1:15 pm Jan 8 - Jan 29
6035 12:15 pm 2:05 pm Dec 29 - Jan 2
6035 12:15 pm 2:05 pm Dec 21 - Dec 28
4914 1:40 pm 3:30 pm Dec 21 - Jan 2
2759 3:30 pm 5:15 pm Jan 7 - Mar 4
1261 3:35 pm 5:30 pm Dec 24 - Dec 24
1863 3:35 pm 5:30 pm Dec 31 - Dec 31
1491 3:50 pm 5:45 pm Dec 17 - Dec 17
3383 4:25 pm 6:20 pm Dec 1 - Dec 20
3383 4:25 pm 6:20 pm Jan 1 - Jan 4
3735 4:25 pm 6:20 pm Dec 25 - Dec 25
612 4:40 pm 6:30 pm Jan 5 - Mar 8
5213 4:50 pm 6:50 pm Dec 21 - Jan 2
5302 5:05 pm 6:55 pm Jan 8 - Jan 29
1937 9:25 pm 11:20 pm Dec 25 - Dec 25
254 9:25 pm 11:20 pm Dec 17 - Dec 20
254 9:25 pm 11:20 pm Jan 1 - Jan 3
254 9:25 pm 11:20 pm Dec 1 - Dec 16
3711 11:15 pm 1:05 am Dec 21 - Jan 2
* 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

Boston
$200
Destination

Chicago
$200
Airlines