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Recent Southwest flights to Chicago found by users

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Cheap Southwest Flight Deals to Chicago

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5:00 am - 12:15 pmBOS-ORD

8h 15m1 stop

1:45 pm - 10:15 pmORD-BOS

7h 30m1 stop

$137Southwest

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Fri, Dec 12 - Tue, Dec 16

5:00 am - 12:15 pmBOS-ORD

8h 15m1 stop

1:45 pm - 10:15 pmORD-BOS

7h 30m1 stop

$142Southwest

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Sun, Dec 7 - Thu, Dec 11

5:00 am - 12:15 pmBOS-ORD

8h 15m1 stop

5:15 pm - 12:45 amORD-BOS

6h 30m1 stop

$144Southwest

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Fri, Dec 12 - Mon, Dec 22

5:00 am - 12:15 pmBOS-ORD

8h 15m1 stop

1:45 pm - 10:15 pmORD-BOS

7h 30m1 stop

$147Southwest

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Sun, Nov 23 - Tue, Dec 2

6:15 am - 12:15 pmBWI-ORD

7h 00m1 stop

1:45 pm - 6:50 pmORD-BWI

4h 05m1 stop

$159Southwest

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Mon, Nov 24 - Mon, Nov 24

6:15 am - 12:15 pmBWI-ORD

7h 00m1 stop

1:45 pm - 9:20 pmORD-BWI

6h 35m2 stops

$164Southwest

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Mon, Nov 24 - Mon, Nov 24

5:00 am - 12:15 pmBOS-ORD

8h 15m1 stop

5:15 pm - 12:45 amORD-BOS

6h 30m1 stop

$187Southwest

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Mon, Nov 24 - Wed, Nov 26

9:05 am - 9:50 pmBOS-ORD

13h 45m2 stops

1:45 pm - 10:15 pmORD-BOS

7h 30m1 stop

$193Southwest

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Wed, Dec 17 - Thu, Dec 25

5:00 am - 12:15 pmBOS-ORD

8h 15m1 stop

5:15 pm - 12:45 amORD-BOS

6h 30m1 stop

$195Southwest

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Fri, Dec 19 - Mon, Dec 22

12:20 pm - 9:50 pmBOS-ORD

10h 30m2 stops

1:45 pm - 10:15 pmORD-BOS

7h 30m1 stop

$198Southwest

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Mon, Dec 8 - Thu, Dec 11

Southwest flights to Chicago at a glance

Direct flights	None

There are no direct flights from United States to Chicago. Popular non-direct routes for this connection are Hartford Bradley Intl Airport - Chicago Midway Airport, Indianapolis Airport - Chicago Midway Airport and Birmingham Airport - Chicago Midway Airport.

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Insights on Southwest flights to Chicago

Data designed to help you find the right flight

What is the cheapest month to fly Economy Class to Chicago?

In general, October is the cheapest month to fly Economy Class from United States to Chicago. Due to it being the ‘off-season’ during this time, you can expect Economy Class flight prices to be around $208. If you aren’t able to travel during the month of October, then book Economy Class flights to Chicago from United States during August instead. Economy Class flights to Chicago in August, while not as cheap as those in October, still average around $237.

What is the cheapest day to depart on your Economy Class flight to Chicago?

The cheapest day to depart from United States to Chicago is on a Wednesday when prices can be found for as low as $158. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average Economy Class ticket price to Chicago on a Monday is $258.

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from United States when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $335 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from United States for as low as $206 on momondo.

What is the cheapest United States to Chicago flight route?

Fly from Boston Logan Intl to Chicago Midway for the best United States - Chicago flight prices

What cabin class options are available on United States to Chicago flights?

There is only 1 cabin class available to choose from on United States to Chicago flights.

Can stopping save me money on United States to Chicago flights?

No. A direct flight is the cheapest option for a flight between United States to Chicago.

Frequently asked questions about flights to Chicago with Southwest

Is Southwest generally cheaper than other airlines for flights to Chicago?

Lots of factors influence the price of a flight, whether that's with Southwest or other airlines so it is best to search and compare before booking. The airline flying to Chicago with the cheapest average return price tends to be Allegiant Air.