Flight Routes 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
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
07/26/26
1 Stopover (ATL)
F93085, F92779
26h 00min
Return
08/05/26
1 Stopover (ATL)
F92292, F93086
14h 57min
Frontier Airlines ?
$377
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
06/25/26
1 Stopover (ATL)
F93085, F92291
15h 06min
Return
06/30/26
1 Stopover (ATL)
F92144, F93512
11h 01min
Frontier Airlines ?
$466
found yesterday
Boston
Chicago Midway
Outbound
06/25/26
1 Stopover (ATL)
F93511, F92291
09h 24min
Return
06/30/26
1 Stopover (ATL)
F92144, F93512
11h 01min
Frontier Airlines
$589
found yesterday
Boston
Chicago Midway
Please note: transfer for connecting flight
Outbound
06/25/26
1 Stopover (ATL)
F93511, F92291
09h 24min
Return
06/30/26
1 Stopover (YTZ)
PD2388, TS7356
05h 21min
Frontier Airlines
$642
found yesterday
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
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
Boston
Chicago Midway
Outbound
06/25/26
1 Stopover (DTW)
DL1019, DL4684
04h 12min
Return
06/30/26
1 Stopover (ATL)
DL1063, DL0821
08h 56min
Delta Air Lines ?
$3,004
found yesterday
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 USD
37 %
1 stopover Philadelphia International Airport, PA
05h 45min, from 217 USD
32 %
1 stopover Toronto - City Centre Airport
10h 17min, from 550 USD
21 %

Important flight information

Flight information: Boston - Chicago Midway

Roundtrip from 296,99 USD
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