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
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 Boston Logan International to Chicago Midway

(Round-trip)
Depart: Thu Aug 10 2017 Return: Mon Aug 14 2017 Trip spans 5 days
Southwest
Southwest
BOS
1:50a
MDW
4:25a
2h 35m
nonstop
MDW
6:35p
BOS
8:50p
2h 15m
nonstop
Depart: Fri Mar 3 2017 Return: Wed Mar 15 2017 Trip spans 12 days
Delta
Delta
BOS
9:36a
MDW
2:04p
4h 28m
1 stop
MDW
9:03a
BOS
12:55p
3h 52m
1 stop
Depart: Tue Aug 8 2017 Return: Mon Aug 14 2017 Trip spans 7 days
Southwest
Southwest
BOS
1:50a
MDW
4:25a
2h 35m
nonstop
MDW
6:35p
BOS
8:50p
2h 15m
nonstop
Depart: Sun Mar 5 2017 Return: Mon Mar 6 2017 Trip spans 2 days
Delta
Delta
BOS
1:55a
MDW
8:33a
6h 38m
1 stop
MDW
4:14a
BOS
9:56a
5h 42m
1 stop
Depart: Mon Mar 6 2017 Return: Tue Mar 7 2017 Trip spans 2 days
Delta
Delta
BOS
7:34a
MDW
12:06p
4h 32m
1 stop
MDW
1:40p
BOS
5:58p
4h 18m
1 stop
Depart: Tue Mar 7 2017 Return: Wed Mar 8 2017 Trip spans 2 days
Delta
Delta
BOS
7:34a
MDW
12:06p
4h 32m
1 stop
MDW
1:50a
BOS
5:59a
4h 09m
1 stop
Depart: Fri Aug 11 2017 Return: Mon Aug 14 2017 Trip spans 4 days
Southwest
Southwest
BOS
3:05p
MDW
6:00p
2h 55m
nonstop
MDW
6:35p
BOS
8:50p
2h 15m
nonstop
Depart: Wed Mar 8 2017 Return: Thu Mar 9 2017 Trip spans 2 days
Delta
Delta
BOS
9:36a
MDW
2:04p
4h 28m
1 stop
MDW
4:22a
BOS
8:02a
3h 40m
1 stop
Depart: Thu Mar 9 2017 Return: Fri Mar 10 2017 Trip spans 2 days
Delta
Delta
BOS
12:40a
MDW
7:14a
6h 34m
1 stop
MDW
1:45a
BOS
8:02a
6h 17m
1 stop
Depart: Tue Mar 14 2017 Return: Wed Mar 15 2017 Trip spans 2 days
Delta
Delta
BOS
12:40p
MDW
5:21p
4h 41m
1 stop
MDW
7:00a
BOS
12:05p
5h 05m
1 stop
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
Delta
Delta
BOS
10:37a
MDW
3:10p
4h 33m
1 stop
MDW
9:03a
BOS
2:38p
5h 35m
1 stop
Depart: Thu Mar 16 2017 Return: Tue Mar 21 2017 Trip spans 6 days
Delta
Delta
BOS
1:36a
MDW
5:47a
4h 11m
1 stop
MDW
8:11a
BOS
4:28p
8h 17m
1 stop
Depart: Tue Mar 21 2017 Return: Wed Mar 22 2017 Trip spans 2 days
Delta
Delta
BOS
10:37a
MDW
3:10p
4h 33m
1 stop
MDW
9:03a
BOS
2:38p
5h 35m
1 stop
Depart: Wed Mar 22 2017 Return: Tue Mar 28 2017 Trip spans 7 days
Delta
Delta
BOS
10:37a
MDW
3:10p
4h 33m
1 stop
MDW
7:00a
BOS
12:05p
5h 05m
1 stop
Depart: Thu Mar 23 2017 Return: Tue Mar 28 2017 Trip spans 6 days
Delta
Delta
BOS
2:55a
MDW
9:28a
6h 33m
1 stop
MDW
11:17a
BOS
4:28p
5h 11m
1 stop
Depart: Sat Mar 25 2017 Return: Tue Mar 28 2017 Trip spans 4 days
Delta
Delta
BOS
1:55a
MDW
7:28a
5h 33m
1 stop
MDW
7:00a
BOS
2:00p
7h 00m
1 stop
Depart: Mon Mar 27 2017 Return: Tue Mar 28 2017 Trip spans 2 days
Delta
Delta
BOS
12:30p
MDW
7:11p
6h 41m
1 stop
MDW
8:11a
BOS
2:00p
5h 49m
1 stop
Depart: Tue Mar 28 2017 Return: Wed Mar 29 2017 Trip spans 2 days
Delta
Delta
BOS
1:36a
MDW
5:47a
4h 11m
1 stop
MDW
7:00a
BOS
12:05p
5h 05m
1 stop
Depart: Wed Mar 29 2017 Return: Fri Mar 31 2017 Trip spans 3 days
Delta
Delta
BOS
1:36a
MDW
5:47a
4h 11m
1 stop
MDW
1:32p
BOS
7:07p
5h 35m
1 stop
Depart: Thu Mar 30 2017 Return: Tue Apr 4 2017 Trip spans 6 days
Delta
Delta
BOS
1:36a
MDW
5:47a
4h 11m
1 stop
MDW
2:45a
BOS
6:58a
4h 13m
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
1822 5:25 am 7:10 am Mar 9 - Mar 10
1822 5:25 am 7:10 am Mar 13 - Apr 24
4872 5:35 am 7:20 am Mar 18 - Apr 22
4872 5:35 am 7:20 am Mar 11 - Mar 11
1621 5:50 am 7:45 am Feb 16 - Mar 8
3292 6:00 am 7:50 am Mar 12 - Apr 23
2497 6:20 am 8:15 am Feb 19 - Mar 5
1734 8:35 am 10:20 am Mar 13 - Apr 24
1734 8:35 am 10:20 am Mar 9 - Mar 10
3068 8:55 am 10:45 am Mar 12 - Apr 23
428 11:15 am 1:05 pm Feb 16 - Mar 8
3435 11:25 am 1:15 pm Feb 19 - Mar 5
1220 11:40 am 1:25 pm Mar 18 - Apr 22
1220 11:40 am 1:25 pm Mar 11 - Mar 11
267 3:45 pm 5:25 pm Mar 11 - Mar 11
267 3:45 pm 5:25 pm Mar 18 - Apr 22
4046 4:25 pm 6:05 pm Mar 13 - Apr 24
4046 4:25 pm 6:05 pm Mar 9 - Mar 10
5478 4:30 pm 6:10 pm Mar 12 - Apr 23
612 4:40 pm 6:30 pm Feb 16 - Mar 8
5302 5:05 pm 6:55 pm Feb 19 - Mar 5
* 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

Boston
$166
Destination

Chicago
$166
Airlines Airline reviews

5 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 9.5.

Overall
9.6
Boarding
10.0
Crew
10.0
Comfort
8.8
Food
9.2
Entertainment
9.2