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
10/09/25
1 Stopover (MIA)
F91435, F92109
10h 43min
Return
11/01/25
1 Stopover (MIA)
F92110, F91436
18h 31min
Frontier Airlines
$249
Boston
Chicago Midway
Pay attention to transfer at connecting flight
Outbound
10/18/25
3 Stopovers (FLL, PIT, PGD)
NK2887, NK0228, G41110, G42478
25h 35min
Return
11/17/25
1 Stopover (TYS)
G41432, G41397
16h 31min
Spirit Airlines, Allegiant Air
$264
Best option
Boston
Chicago Midway
Outbound
09/19/25
1 Stopover (ATL)
DL0923, DL1739
08h 54min
Return
09/29/25
1 Stopover (DTW)
DL3501, DL1187
04h 35min
Delta Air Lines ?
$346
Boston
Chicago Midway
Outbound
09/04/25
1 Stopover (TPA)
F91215, F93899
26h 54min
Return
09/28/25
1 Stopover (MCO)
F93854, F93348
22h 59min
Frontier Airlines
$250
Boston
Chicago Midway
Outbound
10/09/25
1 Stopover (MIA)
F91435, F92109
10h 43min
Return
11/01/25
1 Stopover (MIA)
F92110, F91436
18h 31min
Frontier Airlines
$260
Boston
Chicago Midway
Outbound
09/04/25
1 Stopover (TPA)
F91215, F93899
26h 54min
Return
09/28/25
1 Stopover (MCO)
F93854, F93348
22h 59min
Frontier Airlines
$261
Boston
Chicago Midway
Pay attention to transfer at connecting flight
Outbound
09/19/25
1 Stopover (AVL)
G40226, G40513
08h 44min
Return
09/29/25
1 Stopover (TYS)
G43021, G41397
13h 27min
Allegiant Air
$297
Boston
Chicago Midway
Outbound
08/14/25
1 Stopover (MSP)
DL1138, DL3545
06h 52min
Return
09/11/25
1 Stopover (DTW)
DL3858, DL1171
05h 18min
Delta Air Lines ?
$430
Boston
Chicago Midway
Outbound
10/18/25
2 Stopovers (MSP, VPS)
SY0254, SY1811, G43078
28h 47min
Return
11/17/25
1 Stopover (TYS)
G41432, G41397
16h 31min
Sun Country Airlines, Allegiant Air ?
$449
Boston
Chicago Midway
Outbound
10/18/25
2 Stopovers (MSP, VPS)
SY0254, SY1811, G43078
28h 47min
Return
10/24/25
1 Stopover (TYS)
G41440, G43026
18h 26min
Sun Country Airlines, Allegiant Air ?
$493
Prices based on recent searches, subject to last-minute changes
Page 1 / 1

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 $248.27
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