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

We've found the cheapest flights to Chicago

Returns from £121.28

One-way from £60.25

Getting to Logan International from Midway is very straight forward. There are 3 airliners who all offer direct flights several times a week. 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 Airlines222222305:4519:50VIEW FLIGHTS
NetJets001000016:0016:00VIEW FLIGHTS
Flexjet100000019:4519:45VIEW FLIGHTS

Southwest Airlines offer the highest number of flights for this route with departures times between 05:45 and 19:50.

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
06:30
AirlineFlight  No
Southwest AirlinesWN1159
11:35
AirlineFlight  No
Southwest AirlinesWN2663
19:45
AirlineFlight  No
FlexjetLXJ303
VIEW FLIGHTS
Tuesday
05:45
AirlineFlight  No
Southwest AirlinesWN4309
12:30
AirlineFlight  No
Southwest AirlinesWN1159
VIEW FLIGHTS
Wednesday
05:45
AirlineFlight  No
Southwest AirlinesWN4309
12:30
AirlineFlight  No
Southwest AirlinesWN1159
16:00
AirlineFlight  No
NetJetsEJA219
VIEW FLIGHTS
Thursday
06:30
AirlineFlight  No
Southwest AirlinesWN1159
11:35
AirlineFlight  No
Southwest AirlinesWN2663
VIEW FLIGHTS
Friday
06:30
AirlineFlight  No
Southwest AirlinesWN1159
11:35
AirlineFlight  No
Southwest AirlinesWN2663
VIEW FLIGHTS
Saturday
06:30
AirlineFlight  No
Southwest AirlinesWN1159
18:25
AirlineFlight  No
Southwest AirlinesWN4309
VIEW FLIGHTS
Sunday
06:00
AirlineFlight  No
Southwest AirlinesWN3190
12:55
AirlineFlight  No
Southwest AirlinesWN1159
19:50
AirlineFlight  No
Southwest AirlinesWN2330
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
RouteStopsDistanceFlying Time
Windsor Locks to Chicago Midway 02 Hours 17 Minutes
Bedford Hanscom to Chicago Midway 02 Hours 25 Minutes
Manchester boston Regional to Chicago Midway 02 Hours 24 Minutes
Providence to Chicago Midway 02 Hours 24 Minutes

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!

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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 £60.25 ($78 €71.65)
£60.25
$78 | €71.65
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 £121.28 ($157 €144.23)
£121.28
$157 | €144.23
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 £37.85 ($49 €45.01)
£37.85
$49 | €45.01
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 £77.25 ($100 €91.87)
£77.25
$100 | €91.87
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

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

Who flies from Boston to Chicago?
The following airlines fly from Boston (BOS) to Chicago (MDW): Flexjet, NetJets, 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.

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