Cheap flights from Boston to Chicago Midway Airport

Round-trip
1 adult
Economy
From?
To?
Tue 6/22
Tue 6/29

Flight information for Boston to Chicago Midway Airport
(BOS to MDW)

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago Midway Airport
Best Price Found$117The best flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $117
Fastest flight time4h 10mThe fastest flight from Boston to Chicago Midway Airport takes 4h 10m
Direct flightsNoneThere are no direct flights from Boston to Chicago Midway Airport. Popular non-direct route for this connection is Boston Logan Intl Airport - Chicago Midway Airport.

How to get the cheapest flight ticket from Boston to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Boston to Chicago Midway Airport?

August

The cheapest time of year to fly to Chicago Midway Airport from Boston is August. Most expensive is June

What is the cheapest airline that flies to Chicago Midway Airport from Boston?

Spirit Airlines

American Airlines, Delta, and JetBlue are the most popular carriers operating from Boston to Chicago Midway Airport

How far in advance should you book Boston to Chicago Midway Airport flights?

20 days before

The cheapest time to buy a flight from Boston to Chicago Midway Airport is approximately 20 days to departure


Easily compare round-trip flights from Boston to Chicago Midway Airport

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago Midway Airport by changing tabs
Delta
Jul 14
BOS1:35 amBoston Logan Intl
4h 10m
1 stop
MDW5:45 amChicago Midway
Jul 21
MDW1:15 pmChicago Midway
4h 36m
1 stop
BOS5:51 pmBoston Logan Intl
Delta
Jul 14
BOS1:35 amBoston Logan Intl
4h 10m
1 stop
MDW5:45 amChicago Midway
Jul 20
MDW9:35 amChicago Midway
5h 46m
1 stop
BOS3:21 pmBoston Logan Intl
Delta
Jul 20
BOS1:35 amBoston Logan Intl
4h 10m
1 stop
MDW5:45 amChicago Midway
Jul 20
MDW9:35 amChicago Midway
5h 46m
1 stop
BOS3:21 pmBoston Logan Intl
Delta
Aug 29
BOS1:35 amBoston Logan Intl
4h 10m
1 stop
MDW5:45 amChicago Midway
Sep 5
MDW12:34 pmChicago Midway
6h 18m
1 stop
BOS6:52 pmBoston Logan Intl
Delta
Jun 29
BOS1:35 amBoston Logan Intl
4h 15m
1 stop
MDW5:50 amChicago Midway
Aug 10
MDW12:34 pmChicago Midway
6h 18m
1 stop
BOS6:52 pmBoston Logan Intl
Delta
Jul 28
BOS2:36 pmBoston Logan Intl
6h 05m
1 stop
MDW8:41 pmChicago Midway
Aug 3
MDW1:15 pmChicago Midway
4h 36m
1 stop
BOS5:51 pmBoston Logan Intl

Find the cheapest one-way flights from Boston to Chicago Midway Airport

If you're looking for one-way flights from Boston to Chicago Midway Airport, view some of our deals below provided by Allegiant Air and Delta
Delta
Jul 14
BOS1:35 amBoston Logan Intl
4h 10m
1 stop
MDW5:45 amChicago Midway
Delta
Jul 27
BOS1:35 amBoston Logan Intl
4h 10m
1 stop
MDW5:45 amChicago Midway
Delta
Jun 23
BOS1:35 amBoston Logan Intl
4h 15m
1 stop
MDW5:50 amChicago Midway

Best airlines flying from Boston to Chicago Midway Airport

Compare and see reviews for airlines that fly from Boston to Chicago Midway Airport with momondo
AirlineRatingFree CancellationPrice
United Airlines
PriceFrom $114
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Cons: Sarasota ticketing agent was not very nice at all 😟 Houston Gate agent was not nice either. We were treated like we were stupid for asking questions. I hope it’s not racism issues. I wished I had taken their names.

1 / 10
Spirit Airlines
PriceFrom $125
Free Cancellation
Rating
7.1
7.4

Boarding

6.8

Comfort

7.7

Crew

6.3

Entertainment

6.5

Food

Reviews

Pros: Well, it was not very comfortable and we were delayed for an hour. And a crew member was sick.

Cons: Mostly everything.

1 / 10
American Airlines
PriceFrom $143
Free Cancellation
Rating
7.2
7.5

Boarding

7.1

Comfort

7.9

Crew

7.1

Entertainment

6.8

Food

Reviews

Pros: Nothing

Cons: Not charging me 100 dollars For a luggage that was 56 pounds

1 / 10
JetBlue
PriceFrom $146
Free Cancellation
Rating
8.0
8.3

Boarding

8.1

Comfort

8.5

Crew

7.9

Entertainment

7.6

Food

Reviews

Cons: Seat 14A had malfunctioning audio and the internet connection made it hard to stream

1 / 10
Delta
PriceFrom $160
Free Cancellation
Rating
8.1
8.3

Boarding

8.4

Comfort

8.3

Crew

7.9

Entertainment

8.1

Food

Reviews

Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.

1 / 10
Southwest
PriceFrom $185
Free Cancellation
Rating
8.4
8.6

Boarding

8.5

Comfort

8.8

Crew

7.6

Entertainment

7.8

Food

Reviews

Pros: The plane was new and the seats were nice.

1 / 10

  • Are airlines flying from Boston Logan Intl to Chicago Midway offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from Boston Logan Intl to Chicago Midway, such as Delta, United Airlines, and American Airlines may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.


Alternative routes for Boston to Chicago Midway Airport

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Boston to Chicago O'Hare Intl Airport Flights
Fastest flight time2h 33m
Cheapest price$54
Worcester, Massachusetts to Chicago O'Hare Intl Airport Flights
Fastest flight time10h 33m
Cheapest price$8,732