Direct flight tickets from Boston to Chicago

All flight schedules from Boston Logan International Airport , Massachusetts , USA to Chicago Midway International , Illinois , USA. This route is operated by Southwest Airlines and the flight time is 3 hours and 00 minutes. The distance is 863 miles.

BOS Boston Logan International Airport
USA
Boston , MA , USA
MDW Chicago Midway International
USA
Chicago , IL , USA
CHANGE DIRECTION
Flight time
3h 00m
Flight distance
863mi, 1389km
Flights from Boston to Chicago route map
VIEW LARGER MAP
USA
USA
Boston , MA
aircraft image
USA
USA
Chicago , IL
Distance
863 miles · (1389 km)
Flight time
3 hours and 00 minutes

Airlines that fly direct from Boston (BOS) to Chicago (MDW)

  • Southwest Airlines
    S
    M
    T
    W
    T
    F
    S
    Low-cost airline
    2–3 daily flights
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BOS MDW
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MONTHLY
WN
WEEKLY

Boston (BOS) to Chicago (MDW) flight schedule

The monthly calendar shows every direct flight departure from Boston Logan International Airport (BOS) with all airlines. Click on a date to see a list of flights or search for the best prices.

Southwest Airlines flight schedule from Boston to Chicago

All weekly departures with Southwest Airlines. The week calendar shows every flight departure from Boston (BOS) to Chicago (MDW). Click on a blue date to see a list of flights.

Week 46 (Nov 10 - Nov 16)
  • Week 44 (Oct 27 - Nov 2)
  • Week 45 (Nov 3 - Nov 9)
  • Week 46 (Nov 10 - Nov 16)
  • Week 47 (Nov 17 - Nov 23)
  • Week 48 (Nov 24 - Nov 30)
  • Week 49 (Dec 1 - Dec 7)
  • Week 50 (Dec 8 - Dec 14)
  • Week 51 (Dec 15 - Dec 21)
  • Week 52 (Dec 22 - Dec 28)
  • Week 1 (Dec 29 - Jan 4)
  • Week 2 (Jan 5 - Jan 11)
  • Week 3 (Jan 12 - Jan 18)
  • Week 4 (Jan 19 - Jan 25)
  • Week 5 (Jan 26 - Feb 1)
  • Week 6 (Feb 2 - Feb 8)
  • Week 7 (Feb 9 - Feb 15)
  • Week 8 (Feb 16 - Feb 22)
  • Week 9 (Feb 23 - Mar 1)
  • Week 10 (Mar 2 - Mar 8)
  • Week 11 (Mar 9 - Mar 15)
  • Week 12 (Mar 16 - Mar 22)
  • Week 13 (Mar 23 - Mar 29)
  • Week 14 (Mar 30 - Apr 5)
  • Week 15 (Apr 6 - Apr 12)
  • Week 16 (Apr 13 - Apr 19)
  • Week 17 (Apr 20 - Apr 26)
  • Week 18 (Apr 27 - May 3)
  • Week 19 (May 4 - May 10)
  • Week 20 (May 11 - May 17)
  • Week 21 (May 18 - May 24)
  • Week 22 (May 25 - May 31)
  • Week 23 (Jun 1 - Jun 7)
  • Week 24 (Jun 8 - Jun 14)
  • Week 25 (Jun 15 - Jun 21)
  • Week 26 (Jun 22 - Jun 28)
  • Week 27 (Jun 29 - Jul 5)
  • Week 28 (Jul 6 - Jul 12)
  • Week 29 (Jul 13 - Jul 19)
  • Week 30 (Jul 20 - Jul 26)
  • Week 31 (Jul 27 - Aug 2)
  • Week 32 (Aug 3 - Aug 9)
Flight
Mon
Nov 10
Tue
Nov 11
Wed
Nov 12
Thu
Nov 13
Fri
Nov 14
Sat
Nov 15
Sun
Nov 16
WN2012
05:15
13:35
13:35
05:15
05:15
05:20
05:15
WN1432
13:45
05:30
05:30
13:45
13:45
12:35
13:45
WN1030
18:55
----
----
18:55
18:55
16:45
18:55
Flight time
2h 35m - 3h 00m
Earliest flight
05:15
Last flight
21:35
Distance
863 miles (1389 km)
Cheapest month
April
Airlines
1 (Show)
Flights per week
44
Departing Terminal (BOS)
Terminal B
America/New York (UTC-4)
America/Chicago (UTC-5)
MDW -1 hour behind

US
Arriving at Chicago Midway (MDW) , Illinois

Chicago Midway International (MDW) is a large airport in USA. You can fly to 97 destinations with 6 airlines in scheduled passenger traffic.

Show all flights from MDW

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US
Departing from Boston Logan Airport (BOS) , Massachusetts

Boston Logan International Airport (BOS) is a large airport in USA. You can fly to 151 destinations with 46 airlines in scheduled passenger traffic.

Show all flights from BOS

Airlines operating from nearby alternative airports from Boston to Chicago

The airlines below are departing from or arriving to other airports in the same city or very close.

American Airlines
Oneworld
Boston Logan International Airport Chicago O Hare International
Duration
3 hours and 32 minutes
JetBlue
Boston Logan International Airport Chicago O Hare International
Duration
3 hours and 20 minutes
Spirit
Boston Logan International Airport Chicago O Hare International
Duration
2 hours and 53 minutes
United
Star Alliance
Boston Logan International Airport Chicago O Hare International
Duration
3 hours and 06 minutes
Iberia
Oneworld
Boston Logan International Airport Chicago O Hare International
Duration
2 hours and 50 minutes
Delta
Sky Team
Boston Logan International Airport Chicago O Hare International
Duration
3 hours and 10 minutes
Show detailed flight schedule from BOS to ORD

Boston - Chicago Airfare price statistics

$250
Approximate

The numbers are avarage prices found based on user searches for direct flights between Boston Logan International Airport and Chicago Midway International. Its calculated from the cheapest prices found per month for a round-trip with 1 adult and can vary depending on the amount of data we have for this particular route.

$177
Jan
$466
Feb
$141
Mar
$106
Apr
$168
May
$223
Jun
$288
Jul
$442
Aug
$321
Sep
$212
Oct
$347
Nov
$168
Dec

Approximate prices for one round-trip flight from Boston (BOS) to Chicago (MDW). Graph is not to scale.

CLICK HERE FOR EXACT PRICES

Type of aircraft(s) on this route

Below is a list of aircraft types we have within our database with flights on this route. You can also see the aircrafts seat capacity together with classes.

Boeing 737MAX 8 Passenger
Southwest Airlines
Boeing 737MAX 8 Passenger illustration
Boeing 737MAX 8 Passenger illustration
175 seats
 (All economy)
Boeing 737-800 (winglets) Passenger/BBJ2
Southwest Airlines
Boeing 737-800 (winglets) Passenger/BBJ2 illustration
Boeing 737-800 (winglets) Passenger/BBJ2 illustration
165 seats
 (All economy)
ROUTE EXPLORING

Boston Logan International Airport - all destinations

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Boston flight map

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Round trip
1 adult
Economy

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Frequently Asked Questions about Flights (FAQ)

  • The flight between Boston (BOS) and Chicago (MDW) typically takes about 2 hour and 45 minute.
  • There are 2 direct flights every day.
  • The flight numbers are WN117, WN187, WN331, WN527, WN557, WN558, WN699, WN700 together with 36 additional flights.
  • From Boston you will fly out from Boston Logan International Airport (BOS) and you will be landing at Chicago Midway International (MDW).
  • Boeing 737 flies this route operated by Southwest.
  • Southwest have non-stop flights to Chicago.
  • They will depart from terminal B.
VIEW IN
MAP EXPLORER
Flights from Boston to Chicago route map
Non-stop flights from BOS to MDW
863 miles (1389 km) · 3 hours and 00 minutes
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Popular routes from Boston

Southwest Airlines Southwest Airlines routes

Boston (BOS) - Baltimore (BWI)

US

Boston (BOS) - Nashville (BNA)

US

Boston (BOS) - Saint Louis (STL)

US

Boston (BOS) - Denver (DEN)

US

Boston (BOS) - Austin (AUS)

US

For more destinations from Boston with Southwest Airlines (WN), check out the Southwest Airlines route map .

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