Southwest Airlines Boston to Chicago Flights

Return flight: Chicago – Boston
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Cheapflightsplus.com will find cheap Southwest Airlines flights from Boston to Chicago. Compare airline ticket prices and book air tickets starting from $87 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Southwest Airlines, arrivals and departure details below.

Find Cheap Airfare Boston (MA) — Chicago (IL) by Southwest Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in march: one-way - $87, two-way – $149.
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Cheap Flights from Boston to Chicago by Southwest Airlines

Look at the list of plane tickets for the most popular direct flights by Southwest Airlines, their prices start from $87. The fastest nonstop flight takes 2h 45m. There’re no connecting flights.
Price Departure Arrival Flight Time Airline Flight
from $87
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7:00 am
Boston
Logan
 8:45 am
Chicago
Midway
 2h 45m Southwest Airlines
WN787
from $87
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6:00 pm
Boston
Logan
 7:45 pm
Chicago
Midway
 2h 45m Southwest Airlines
WN1549
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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 03/14/2025
Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
6:00 pm — 7:45 pm
6:00 pm — 7:45 pm WN1549 Southwest Airlines
Boston — Chicago
2h 45m
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from$87
7:00 am — 8:45 am
7:00 am — 8:45 am WN787 Southwest Airlines
Boston — Chicago
2h 45m
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from$87
*Departure and arrival times are local. Last updated on 03/14/2025

Flight Information

There are 2 flights by Southwest Airlines from Boston to Chicago every week with departures from Logan, Boston City Heliport, Boston RT128 Rail, Boston South Rail. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 6:00 pm to 7:00 am. Nonstop flight is 2h 45m. The time difference between Boston and Chicago is 1h.

  • The fastest flight 2h 45m
  • Average flight time 2h 45m
  • The earliest flight 6:00 pm
  • The latest flight 7:00 am
  • Distance 852 ml

The cheapest months for traveling to Chicago are november (from 87 $).

The cheapest flight by Southwest Airlines that our users were able to find is $87. This airfare is economy class on one-way WN787 flight for November 12, 2024 leaving Logan in Boston at 7:00 am, it includes all taxes and additional fees.

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Southwest Airlines Airplanes on the Route

List of the most popular Southwest Airlines airplanes flying from Boston to Chicago:

  • Airbus A320
    from $87
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Other Popular Airlines on the Route

Besides Southwest Airlines there are other 1 airline carriers between Boston and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Boston to Chicago.

Nonstop flights

There are 3 direct flights every day from Boston. Airlines and fares are below:

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Connecting Flights

There’re no flights with layovers. Try direct flights or departure from nearby cities.

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  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

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