Find Cheap Flights to Chicago Midway

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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Book cheap flights to Chicago Midway

(Round-trip)
Depart: Mon Jul 3 2017 Return: Tue Jul 4 2017 Trip spans 2 days
Delta
Delta
BOS
MDW
7h 07m
1 stop
MDW
BOS
5h 09m
1 stop
Depart: Wed Aug 16 2017 Return: Fri Aug 18 2017 Trip spans 3 days
Southwest
Southwest
BOS
MDW
2h 35m
nonstop
MDW
BOS
2h 15m
nonstop
Depart: Wed Aug 23 2017 Return: Wed Aug 30 2017 Trip spans 8 days
Delta
Delta
BOS
MDW
6h 07m
1 stop
MDW
BOS
4h 01m
1 stop
Depart: Wed Sep 6 2017 Return: Wed Sep 13 2017 Trip spans 8 days
Delta
Delta
BOS
MDW
4h 05m
1 stop
MDW
BOS
5h 44m
1 stop
Depart: Wed Sep 20 2017 Return: Tue Sep 26 2017 Trip spans 7 days
Delta
Delta
BOS
MDW
6h 27m
1 stop
MDW
BOS
3h 40m
1 stop
Depart: Sat Jul 1 2017 Return: Thu Jul 6 2017 Trip spans 6 days
Major Airline
Major Airline
AUS
MDW
1h 56m
nonstop
MDW
AUS
1h 56m
nonstop
Depart: Tue Oct 3 2017 Return: Sat Oct 7 2017 Trip spans 5 days
Delta
Delta
BOS
MDW
5h 32m
1 stop
MDW
BOS
5h 59m
1 stop
Depart: Tue Oct 10 2017 Return: Tue Oct 17 2017 Trip spans 8 days
Delta
Delta
BOS
MDW
4h 33m
1 stop
MDW
BOS
3h 54m
1 stop
Depart: Sat Sep 23 2017 Return: Wed Sep 27 2017 Trip spans 5 days
Southwest
Southwest
BOS
MDW
2h 40m
nonstop
MDW
BOS
2h 20m
nonstop
Depart: Thu Nov 30 2017 Return: Thu Dec 14 2017 Trip spans 15 days
Delta
Delta
BOS
MDW
5h 37m
1 stop
MDW
BOS
3h 54m
1 stop
Depart: Fri Dec 1 2017 Return: Tue Dec 12 2017 Trip spans 12 days
Delta
Delta
BOS
MDW
4h 33m
1 stop
MDW
BOS
3h 40m
1 stop
Depart: Sun Dec 17 2017 Return: Wed Dec 20 2017 Trip spans 4 days
Delta
Delta
BOS
MDW
4h 34m
1 stop
MDW
BOS
6h 35m
1 stop
Depart: Tue Jul 4 2017 Return: Wed Jul 5 2017 Trip spans 2 days
Delta
Delta
ATL
MDW
1h 59m
nonstop
MDW
ATL
1h 50m
nonstop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 days
Delta
Delta
ATL
MDW
2h 03m
nonstop
MDW
ATL
1h 55m
nonstop
Depart: Tue Aug 8 2017 Return: Tue Aug 15 2017 Trip spans 8 days
Delta
Delta
ATL
MDW
2h 03m
nonstop
MDW
ATL
1h 55m
nonstop
Depart: Tue Jul 4 2017 Return: Tue Jul 11 2017 Trip spans 8 days
Delta
Delta
BWI
MDW
3h 35m
1 stop
MDW
BWI
3h 50m
1 stop
Depart: Sat Jul 15 2017 Return: Tue Jul 18 2017 Trip spans 4 days
Delta
Delta
ATL
MDW
1h 59m
nonstop
MDW
ATL
1h 50m
nonstop
Depart: Tue Jul 25 2017 Return: Wed Jul 26 2017 Trip spans 2 days
Delta
Delta
BWI
MDW
4h 54m
1 stop
MDW
BWI
4h 43m
1 stop
Depart: Tue Aug 8 2017 Return: Tue Aug 15 2017 Trip spans 8 days
Delta
Delta
BWI
MDW
3h 35m
1 stop
MDW
BWI
6h 11m
1 stop
Depart: Sat Aug 19 2017 Return: Wed Aug 23 2017 Trip spans 5 days
Delta
Delta
AUS
MDW
6h 38m
1 stop
MDW
AUS
7h 00m
1 stop
* 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

Baltimore
$202
Atlanta
$197
Austin
$204
Boston
$184
Destination

Chicago
$184
Airlines Airline reviews

8 travelers who booked a flight from Boston to Chicago rated their chosen airlines with an average of 9.0.

Overall
9.3
Boarding
9.5
Crew
9.8
Comfort
8.5
Food
8.8
Entertainment
8.3