Flights from Boston Airport (BOS) to Chicago Midway Airport Airport (MDW)

We've found the cheapest flights to Chicago

Returns from £125.53

One-way from £62.37

Direct flights to Midway from Logan International are only offered by Southwest Airlines as this route is in low demand, so the options are limited. If this route is not ideal, the only other option is to get a flight with a stop over. The official airport code for Logan International is BOS and for Midway it is MDW.

The cost of the flights varies significantly so we can’t provide you an estimate. Prices can be 50% cheaper if you book more than a month in advance. If you know the dates you wish to travel then book you flights as soon as you can. The earlier you book your lights the cheaper they will be. You can get saving of up to 50% of you book 2 or 3 months in advance! Flight to Midway will get more expensive the nearer you get the departure date, so it’s advisable to book in advance if it is possible.

When arriving at Midway don’t forget to set your watch to the local time!

To see all airliners that offer flights between Logan International and Midway please see the table below.

Flights Chart
AirlinerMoTuWeThFrSaSuFirst FlightLast FlightFlights
Southwest Airlines222233306:4019:55VIEW FLIGHTS

Southwest Airlines offer the highest number of flights for this route with departures times between 06:40 and 19:55.

If you wish to book your flight with Southwest Airlines then we advise you book direct from their website at www.southwest.com/?ref=southwestairlines.com. The best discounts can only be obtained from their website.

The flight time for the selected route vary based on the month you will travel, but below we has summarised the most common times they will fly. We recommend you only take these times as guidance and check with appropriate airline for the exact times for the date you depart.

Flights Time In WeekDays
DayFlight TimesFlights
Monday
07:00
AirlineFlight  No
Southwest AirlinesWN787
18:00
AirlineFlight  No
Southwest AirlinesWN1549
VIEW FLIGHTS
Tuesday
07:00
AirlineFlight  No
Southwest AirlinesWN787
18:00
AirlineFlight  No
Southwest AirlinesWN1549
VIEW FLIGHTS
Wednesday
07:00
AirlineFlight  No
Southwest AirlinesWN787
18:00
AirlineFlight  No
Southwest AirlinesWN1549
VIEW FLIGHTS
Thursday
07:00
AirlineFlight  No
Southwest AirlinesWN787
18:00
AirlineFlight  No
Southwest AirlinesWN1549
VIEW FLIGHTS
Friday
06:40
AirlineFlight  No
Southwest AirlinesWN787
14:55
AirlineFlight  No
Southwest AirlinesWN3249
19:55
AirlineFlight  No
Southwest AirlinesWN3586
VIEW FLIGHTS
Saturday
05:05
AirlineFlight  No
Southwest AirlinesWN787
12:05
AirlineFlight  No
Southwest AirlinesWN3249
17:05
AirlineFlight  No
Southwest AirlinesWN3586
VIEW FLIGHTS
Sunday
06:40
AirlineFlight  No
Southwest AirlinesWN787
14:55
AirlineFlight  No
Southwest AirlinesWN3249
19:55
AirlineFlight  No
Southwest AirlinesWN3586
VIEW FLIGHTS

If the airlines stated don’t offer flights that suite your travel times, you could look at alternative options. Below we have summarised flights from alternative departures airports and flights that are not direct.

Alternative Direct Routes

Before you start your journey remember to check you have all your documents; in particular, your passport and flight tickets. You will be surprised at the amount of people of forget these!

Planning a trip? Save money on car hire by booking in advance

Find cheap rental vehicles at Chicago Midway Airport

Flight Price FAQ - Boston (BOS) to Chicago (MDW)

DIRECT Southwest Airlines
What is the cheapest direct flight one way from Boston BOS to Chicago MDW?
The cheapest direct flight one way from Boston BOS to Chicago MDW is £62.37 ($78 €75.06)
£62.37
$78 | €75.06
Check Latest Price
DIRECT Southwest Airlines
What is the cheapest direct return flight from Boston BOS to Chicago MDW?
The cheapest direct return flight from Boston BOS to Chicago MDW is £125.53 ($157 €151.07)
£125.53
$157 | €151.07
Check Latest Price
1+ STOP(S)
What is the cheapest flight one way from Boston BOS to Chicago MDW?
The cheapest flight one way from Boston BOS to Chicago MDW is £39.98 ($50 €48.11)
£39.98
$50 | €48.11
Check Latest Price
1+ STOP(S)
What is the cheapest return flight from Boston BOS to Chicago MDW?
The cheapest return flight from Boston BOS to Chicago MDW is £79.96 ($100 €96.23)
£79.96
$100 | €96.23
Check Latest Price
Important Note: Prices shown are taken from searches performed for flights operating during the current month. Please use the "Latest Price" buttons to get the most up to date airfares.

Compare Flight Prices from BOS to MDW

Was your flight delayed or cancelled?

Was your flight delayed or cancelled?

You may be eligible to receive up to 600 EUR compensation per person in your party.

Claim Now!

Flight Info FAQ - Boston (BOS) to Chicago (MDW)

Who flies from Boston to Chicago?
The following airlines fly from Boston (BOS) to Chicago (MDW): Southwest Airlines.
How far is the flight from Boston to Chicago?
The flight from Boston to Chicago is 1,381KM or 858 miles.
How long does the flight from Boston to Chicago to take?
The flight from Boston to Chicago takes 2 Hours 26 Minutes.

Other Airports Connecting To Chicago Midway Airport in united states

Planning a trip? Save money on car rental by booking in advance

Find cheap vehicle hire deals in Chicago Midway

Useful Information about Chicago Midway Airport

Lounges at Chicago Midway Airport

See all the airport lounges, locations and opening times available at Chicago Midway Airport

View...
Eating and Drinking at Chicago Midway Airport

See all bars and restaurants at Chicago Midway Airport, including locations and if they are before or after check-in

View...
Duty Free Shopping at Chicago Midway Airport

See all shops available at Chicago Midway Airport - plan your duty free shopping in advance

View...
Tourist Attractions in Chicago

Things to see and do in and around Chicago, Illinois...

View...