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Southwest Airlines flights from Boston to Chicago

Southwest Airlines flies Boston to Chicago nonstop 9 times a week, departures from 06:25 to 07:10, 2h 40m in the air. Tickets from $119 (the route's cheapest fare is $114).

Flights from Boston to Chicago

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We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: Boston to Chicago

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

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Southwest Airlines on Boston to Chicago at a glance

flights a week
9
days of operation
Daily
first and last departure
06:25 - 07:10
flight time
2h 40m - 3h
aircraft
Boeing 737, Boeing 737-800
departure terminal
B
cheapest fare, 21 November
$119
cheapest fare on the route
$114

Southwest Airlines Boston to Chicago schedule

9 flights a week. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 845
Southwest Airlines
06:25 Logan International, terminal B
08:15 Chicago Midway International
2h 50m
Sat
WN 2185
Southwest Airlines
07:05 Logan International, terminal B
08:50 Chicago Midway International
2h 45m
Mon, Thu, Fri, Sun
WN 4995
Southwest Airlines
07:10 Logan International, terminal B
08:55 Chicago Midway International
2h 45m
Mon, Tue, Wed, Thu
Boeing 737

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 24 November.

FlightDepartsArrivesDurationDaysAircraft
WN 4999
Southwest Airlines
07:00 Logan International, terminal B
08:45 Chicago Midway International
2h 45m
Seasonal
Boeing 737
WN 4999
Southwest Airlines
07:15 Logan International, terminal B
09:05 Chicago Midway International
2h 50m
Seasonal
Boeing 737
WN 2972
Southwest Airlines
06:45 Logan International, terminal B
08:30 Chicago Midway International
2h 45m
Seasonal
WN 4995
Southwest Airlines
07:15 Logan International, terminal B
09:00 Chicago Midway International
2h 45m
Seasonal
Boeing 737
WN 4127
Southwest Airlines
07:10 Logan International, terminal B
09:10 Chicago Midway International
3h
Seasonal
Boeing 737
WN 4127
Southwest Airlines
07:15 Logan International, terminal B
09:15 Chicago Midway International
3h
Seasonal
Boeing 737
WN 4127
Southwest Airlines
06:35 Logan International, terminal B
08:30 Chicago Midway International
2h 55m
Seasonal
Boeing 737
WN 4695
Southwest Airlines
07:30 Logan International, terminal B
09:15 Chicago Midway International
2h 45m
Seasonal
Boeing 737-800
WN 4679
Southwest Airlines
07:05 Logan International, terminal B
08:55 Chicago Midway International
2h 50m
Seasonal
Boeing 737
WN 4695
Southwest Airlines
07:00 Logan International, terminal B
08:50 Chicago Midway International
2h 50m
Seasonal
Boeing 737
WN 4654
Southwest Airlines
07:30 Logan International, terminal B
09:15 Chicago Midway International
2h 45m
Seasonal
Boeing 737-800
WN 4654
Southwest Airlines
06:40 Logan International, terminal B
08:25 Chicago Midway International
2h 45m
Seasonal
Boeing 737
WN 4654
Southwest Airlines
07:20 Logan International, terminal B
09:05 Chicago Midway International
2h 45m
Seasonal
Boeing 737-800
WN 632
Southwest Airlines
06:30 Logan International, terminal B
08:10 Chicago Midway International
2h 40m
Seasonal
WN 1286
Southwest Airlines
07:40 Logan International, terminal B
09:20 Chicago Midway International
2h 40m
Seasonal
Boeing 737
WN 5325
Southwest Airlines
06:30 Logan International, terminal B
08:10 Chicago Midway International
2h 40m
Seasonal
Boeing 737
WN 632
Southwest Airlines
07:15 Logan International, terminal B
08:55 Chicago Midway International
2h 40m
Seasonal

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 1 hour behind Boston.

Other airlines flying Boston to Chicago

Nonstop flights by the current schedule

American Airlines United Airlines Delta jetBlue All flights Boston to Chicago

Frequently asked questions

How many Southwest Airlines flights are there from Boston to Chicago?
9 nonstop flights a week, 12 flight numbers in the schedule: Daily.
How long is the Southwest Airlines flight from Boston to Chicago?
From 2 hours 40 minutes to 3 hours nonstop, depending on the flight.
Which aircraft does Southwest Airlines fly from Boston to Chicago?
Boeing 737 and Boeing 737-800.
Which terminals does Southwest Airlines use between Boston and Chicago?
Southwest Airlines departs from Logan International, terminal B and arrives at Chicago Midway International.
How much is a Southwest Airlines ticket from Boston to Chicago?
The cheapest Southwest Airlines nonstop fare found recently is $119 for 21 November; the cheapest fare on the route with any airline is $114. The search shows the price for your date.