Flights from Boston to Chicago Midway

Trip type

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
Best option
Boston
Chicago Midway
Outbound
05/16/26
1 Stopover (ATL)
F93085, F92291
14h 31min
Return
05/29/26
1 Stopover (VPS)
G43109, G43100
11h 26min
Frontier Airlines ?
$297
found 3 days ago
Boston
Chicago Midway
Please note: transfer for connecting flight
Outbound
03/28/26
1 Stopover (ATL)
F93511, F92779
10h 33min
Return
04/25/26
1 Stopover (ATL)
F92780, F93086
09h 31min
Frontier Airlines
$500
Boston
Chicago Midway
Outbound
04/03/26
1 Stopover (ATL)
F93511, F92291
25h 41min
Return
04/16/26
1 Stopover (VPS)
G41487, G43066
17h 11min
Frontier Airlines ?
$421
Boston
Chicago Midway
Outbound
03/28/26
1 Stopover (ATL)
F93511, F92779
10h 33min
Return
04/25/26
2 Stopovers (MCO, ATL)
F91536, F91241, F93512
49h 31min
Frontier Airlines ?
$437
Boston
Chicago Midway
Outbound
05/16/26
1 Stopover (ATL)
DL0322, DL1076
08h 14min
Return
05/29/26
1 Stopover (ATL)
DL1728, DL0865
07h 09min
Delta Air Lines ?
$1,315
found 3 days ago
Boston
Chicago Midway
Outbound
03/28/26
1 Stopover (MSP)
DL1103, DL3799
08h 40min
Return
04/25/26
1 Stopover (MSP)
DL3792, DL2614
08h 29min
Delta Air Lines ?
$1,807
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 $296.99
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