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

Q: How long does the flight from Boston to Chicago to take?

The flight from Boston to Chicago takes2 Hours 26 Minutes.

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!

If you plan on flying to Midway Airport (MDW) from Logan International Airport (BOS) you can pre-arrange your long or short term parking at Logan International Airport (BOS).

If you are renting a car at Midway Airport (MDW) it is recommended to fill up the fuel tank before returning the vehicle at the nearest fuel station to Midway Airport (MDW) in order to avoid incurring additional costs. *Please check your rental agreement to understand the fuel policy for your vehicle.

Organise and book your choice of transport to Logan International Airport (BOS):

Ensure your arrival at Midway Airport (MDW) is as stress-free as possible by pre-booking your onward transport - booking early may also save you money:

You can also research and pre-book a hotel near Midway Airport (MDW)

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

Flights Chart

Airliner	Mo	Tu	We	Th	Fr	Sa	Su	First Flight	Last Flight	Flights
Southwest Airlines	2	2	2	2	2	2	3	05:45	19:50	VIEW FLIGHTS
NetJets	0	0	1	0	0	0	0	16:00	16:00	VIEW FLIGHTS
Flexjet	1	0	0	0	0	0	0	19:45	19:45	VIEW 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

Day

Flight Times

Flights

Monday

06:30

Airline	Flight No
Southwest Airlines	WN1159

11:35

Airline	Flight No
Southwest Airlines	WN2663

19:45

Airline	Flight No
Flexjet	LXJ303

VIEW FLIGHTS

Tuesday

05:45

Airline	Flight No
Southwest Airlines	WN4309

12:30

Airline	Flight No
Southwest Airlines	WN1159

VIEW FLIGHTS

Wednesday

05:45

Airline	Flight No
Southwest Airlines	WN4309

12:30

Airline	Flight No
Southwest Airlines	WN1159

16:00

Airline	Flight No
NetJets	EJA219

VIEW FLIGHTS

Thursday

06:30

Airline	Flight No
Southwest Airlines	WN1159

11:35

Airline	Flight No
Southwest Airlines	WN2663

VIEW FLIGHTS

Friday

06:30

Airline	Flight No
Southwest Airlines	WN1159

11:35

Airline	Flight No
Southwest Airlines	WN2663

VIEW FLIGHTS

Saturday

06:30

Airline	Flight No
Southwest Airlines	WN1159

18:25

Airline	Flight No
Southwest Airlines	WN4309

VIEW FLIGHTS

Sunday

06:00

Airline	Flight No
Southwest Airlines	WN3190

12:55

Airline	Flight No
Southwest Airlines	WN1159

19:50

Airline	Flight No
Southwest Airlines	WN2330

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

Route	Stops	Distance	Flying Time
Windsor Locks to Chicago Midway	0		2 Hours 17 Minutes
Bedford Hanscom to Chicago Midway	0		2 Hours 25 Minutes
Manchester boston Regional to Chicago Midway	0		2 Hours 24 Minutes
Providence to Chicago Midway	0		2 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!

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 £60.25 ($78 €71.65)

£60.25

$78 | €71.65

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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

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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.