Flights from Boston to Chicago Midway

Our cheapest offers for flights from Boston to Chicago Midway

Here you can compare cheap flights from Boston (BOS) to Chicago Midway (MDW) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Chicago Midway. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Boston
Chicago Midway
Outbound
04/12/25
1 Stopover (ATL)
F93511, F92779
17h 16min
Return
04/27/25
1 Stopover (ATL)
F92292, F93512
18h 13min
Frontier Airlines ?
$247
found yesterday
Best option
Boston
Chicago Midway
Outbound
04/21/25
1 Stopover (TPA)
F91215, F91185
10h 21min
Return
05/19/25
1 Stopover (MCO)
F93854, F93348
10h 25min
Frontier Airlines
$303
Boston
Chicago Midway
Outbound
04/21/25
2 Stopovers (MIA, ATL)
AA1397, AA0659, F92143
16h 43min
Return
05/19/25
2 Stopovers (ATL, MCO)
F92292, F93976, F93348
29h 08min
American Airlines, Frontier Airlines ?
$303
Boston
Chicago Midway
Outbound
04/21/25
1 Stopover (TPA)
F91215, F91185
10h 21min
Return
05/19/25
1 Stopover (MCO)
F93854, F93348
10h 25min
Frontier Airlines
$313
Boston
Chicago Midway
Outbound
04/21/25
1 Stopover (TPA)
F91215, F91185
10h 21min
Return
05/19/25
1 Stopover (MCO)
F93854, F93348
10h 25min
Frontier Airlines ?
$314
Boston
Chicago Midway
Outbound
06/20/25
1 Stopover (ATL)
F93511, F92779
18h 55min
Return
07/19/25
2 Stopovers (ATL, MSP)
F92292, SY0356, SY0253
27h 59min
Frontier Airlines ?
$427
Boston
Chicago Midway
Outbound
06/10/25
1 Stopover (ATL)
F93511, F92779
18h 55min
Return
06/29/25
1 Stopover (ATL)
F92144, F93512
10h 58min
Frontier Airlines ?
$500
Boston
Chicago Midway
Outbound
06/20/25
1 Stopover (MCO)
F93347, F93853
14h 59min
Return
07/19/25
1 Stopover (MCO)
F93854, F93348
27h 00min
Frontier Airlines
$659
Boston
Chicago Midway
Outbound
06/20/25
1 Stopover (MCO)
F93347, F93853
14h 59min
Return
07/19/25
1 Stopover (MCO)
F93854, F93348
27h 00min
Frontier Airlines
$661
Prices based on recent searches, subject to last-minute changes
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Tips and tricks to help you find cheap flights from Boston to Chicago Midway

Favorite airline: Frontier Airlines
The most popular airline for flights from Boston to Chicago Midway is Frontier Airlines.
Frontier Airlines
52 %
Delta
24 %
Porter Airlines
16 %
Cheapest weekday: Thursday
The cheapest days to fly on this route are Thursday.
Favourite connection: via Orlando
37 % of booked tickets on this route are for flights with a transfer in Orlando.
Route
bookings
1 stopover Orlando International Airport, FL
25h 34min, from $ 396
37 %
1 stopover Philadelphia International Airport, PA
05h 45min, from $ 217
32 %
1 stopover Toronto - City Centre Airport
10h 17min, from $ 550
21 %

Important flight information

Flight information: Boston - Chicago Midway

Roundtrip from $ 246,25
Flight duration min. 02:45 / max. 06:55
Return flight duration min. 02:10/ max. 11:15
Distance 1383 km
Flights per week 23
Departure airport Airport Boston Logan International Airport, MA (BOS)
Arrival airport Airport Chicago Midway International Airport, IL (MDW)
Destination country Flights to United States
Alternative routes to United States
Alternative flights to Chicago Midway
Flight destinations with a similar price