Flights from Boston to Chicago Midway

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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
12/13/24
1 Stopover (ATL)
NK1460, F92779
28h 19min
Return
12/31/24
1 Stopover (ATL)
F92144, F93512
13h 31min
Spirit Airlines, Frontier Airlines ?
$292
Boston
Chicago Midway
Outbound
03/02/25
1 Stopover (ATL)
F93511, F92779
15h 49min
Return
03/07/25
2 Stopovers (ATL, ORD)
F92144, UA1046, UA1495
13h 57min
Frontier Airlines ?
$400
Boston
Chicago Midway
Outbound
12/13/24
1 Stopover (RDU)
F93057, F93717
13h 39min
Return
12/31/24
1 Stopover (MCO)
F91458, F91978
16h 17min
Frontier Airlines
$444
Boston
Chicago Midway
Outbound
12/13/24
1 Stopover (RDU)
F93057, F93717
13h 39min
Return
12/31/24
1 Stopover (MCO)
F91458, F91978
16h 17min
Frontier Airlines
$455
Boston
Chicago Midway
Outbound
02/19/25
1 Stopover (ATL)
NK1179, F92779
15h 49min
Return
03/10/25
1 Stopover (ATL)
F92144, F93512
13h 31min
Spirit Airlines, Frontier Airlines ?
$478
Boston
Chicago Midway
Outbound
03/02/25
1 Stopover (PHL)
F93011, F94367
07h 37min
Return
03/07/25
1 Stopover (RDU)
F93718, F93058
20h 05min
Frontier Airlines
$616
Boston
Chicago Midway
Outbound
03/02/25
1 Stopover (PHL)
F93011, F94367
07h 37min
Return
03/07/25
1 Stopover (RDU)
F93718, F93058
20h 05min
Frontier Airlines
$620
Boston
Chicago Midway
Outbound
02/19/25
1 Stopover (DFW)
F93601, F92882
12h 06min
Return
03/10/25
1 Stopover (PHL)
F91618, F92168
10h 26min
Frontier Airlines
$643
Boston
Chicago Midway
Outbound
02/19/25
1 Stopover (DFW)
F93601, F92882
12h 06min
Return
03/10/25
1 Stopover (PHL)
F91618, F92168
10h 26min
Frontier Airlines
$648
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 %

Flight information: Boston - Chicago Midway

Roundtrip from $291.82
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
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.