Cheap flights from Boston to Chicago Midway Airport

Round-trip
Economy
Boston (BOS)
Chicago (MDW)
Sat 2/20
Sat 2/27
Any month
Compare vs. momondo |

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 $120 The best flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $120
Fastest flight time 6h 27m The fastest flight from Boston to Chicago Midway Airport takes 6h 27m.
Direct flights None There are no direct flights from Boston to Chicago Midway Airport. Popular non-direct route for this connection is Boston Logan Intl - Chicago Midway.

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 day to depart Boston for Chicago Midway Airport?
Wednesday
The cheapest day of the week is typically Wednesday. The most expensive is typically Monday
When is the cheapest time to fly from Boston to Chicago Midway Airport?
at noon
Boston to Chicago Midway Airport flights are approximately 7% more expensive in the afternoon than at noon
What is the cheapest airline that flies to Chicago Midway Airport from Boston?
Spirit Airlines
Spirit Airlines, United Airlines, and American Airlines are the most popular carriers operating from Boston to Chicago Midway Airport
What is the cheapest Boston to Chicago Midway Airport flight route?
Boston Logan Intl - Chicago Midway
Fly from Boston Logan Intl to Chicago Midway for the best Boston - Chicago Midway Airport flight prices
BOS
Boston Logan Intl
MDW
Chicago Midway
How far in advance should you book Boston to Chicago Midway Airport flights?
22 days before
The cheapest time to buy a flight from Boston to Chicago Midway Airport is approximately 22 days to departure
60
Days before departure
0

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
Apr 2
5h 01m
Boston Logan Intl
5h 01m
1 stop
3:39 pm
Chicago Midway
Apr 5
8:35 am
Chicago Midway
4h 10m
1 stop
12:45 pm
Boston Logan Intl
Delta
Jan 29
5h 40m
Boston Logan Intl
5h 40m
1 stop
6:40 am
Chicago Midway
Feb 1
12:15 pm
Chicago Midway
5h 24m
1 stop
5:39 pm
Boston Logan Intl
Delta
Feb 5
5h 45m
Boston Logan Intl
5h 45m
1 stop
6:40 am
Chicago Midway
Feb 8
12:15 pm
Chicago Midway
5h 24m
1 stop
5:39 pm
Boston 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 Delta
Delta
Feb 9
5h 45m
Boston Logan Intl
5h 45m
1 stop
6:40 am
Chicago Midway
Delta
Apr 17
5h 50m
Boston Logan Intl
5h 50m
1 stop
8:00 pm
Chicago Midway
Delta
Jan 26
5h 57m
Boston Logan Intl
5h 57m
1 stop
5:57 pm
Chicago 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
7.0
7.4

Boarding

6.9

Comfort

7.7

Crew

6.5

Entertainment

6.4

Food

Reviews

Pros: The extra legroom for economy plus seats

Cons: The food was tiny and not good

1 / 10
Spirit Airlines
PriceFrom $125
Free Cancellation
Rating
5.6
6.1

Boarding

5.4

Comfort

6.5

Crew

4.6

Entertainment

4.7

Food

Reviews

Pros: but reach destination 45 min.early

Cons: late by 2 hours

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

Boarding

7.1

Comfort

7.8

Crew

6.8

Entertainment

6.7

Food

Reviews

Pros: I didn’t like anything at all

Cons: They have to add electronic devices or charge plug on it

1 / 10
JetBlue
PriceFrom $146
Free Cancellation
Rating
8.1
8.3

Boarding

8.2

Comfort

8.6

Crew

7.9

Entertainment

7.8

Food

Reviews

Pros: Most of the basics were good.

Cons: The flight was substantially delayed and when we got to Chicago we had to wait a long time for a gate agent so that we could deplane because only one gate agent was working at that hour (10:20 p.m.). Also, the flight delay notifications came after I was close to the airport and at the airport--earlier notifications (if possible) would help. The tv/movie portion of the entertainment was not working at all.

1 / 10
Delta
PriceFrom $160
Free Cancellation
Rating
7.9
8.1

Boarding

7.8

Comfort

8.5

Crew

7.8

Entertainment

7.5

Food

Reviews

Cons: The flight attendants were fantastic!

1 / 10
Southwest
PriceFrom $185
Free Cancellation
Rating
8.4
8.7

Boarding

8.4

Comfort

9.0

Crew

8.0

Entertainment

7.8

Food

Reviews

Cons: Nothing. Smooth flight, friendly crew, and early arrival. Can’t be beat!

1 / 10

Which airlines flying from Boston Logan Intl to Chicago Midway have COVID-19 safety policies in place?

Airlines such as Delta have taken additional precautions to make sure you’re safer while traveling. Airlines flying from Boston Logan Intl to Chicago Midway are working to protect travelers. Some of these new policies include temperature checks, pre-flight testing, sanitization of key touchpoints, as well as mask requirements when onboard. Some airlines have even implemented socially distanced seating for a limited time. Policies will vary by airline.

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 time
2h 50m
Cheapest price
$80
Worcester, Massachusetts to Chicago O'Hare Intl Airport Flights
Fastest flight time
10h 33m
Cheapest price
$15,237

Flights from Boston to:

  • Round-trip
  • One-way
  • Multi-city
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First