Is Southwest the cheapest airline to fly with from Washington, D.C. Reagan-National Airport to Chicago?

With an average price of $313 return, Southwest is not the cheapest airline to fly from Washington, D.C. Reagan-National Airport to Chicago with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $207 on average.

Does Southwest fly direct to Chicago from Washington, D.C. Reagan-National Airport?

Yes, Southwest does offer direct flights for the route, with around 34 flights per week.

What’s the cheapest day of the week to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest?

On average, the cheapest day of the week to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest is Friday, when prices are around $78. The most expensive day is generally Saturday, where the average price is around $114.

What’s the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest?

The cheapest month for Southwest flights to Chicago from Washington, D.C. Reagan-National Airport is generally August, where plane tickets cost $111 on average. If possible, try to avoid the most expensive months of May and January, where tickets cost $264 and $322 respectively.

$105 Cheap Southwest Flights from Washington, D.C. Reagan-National Airport to Chicago

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Flight Deals

Cheap Southwest Flight Deals from Washington, D.C. Reagan-National Airport to Chicago

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Washington, D.C. Reagan-National Airport to Chicago

Fri, Oct 31 - Tue, Nov 4

6:00 am - 7:00 amDCA-MDW

2h 00mnonstop

10:05 am - 1:00 pmMDW-DCA

1h 55mnonstop

$223Southwest

Find Deal

Fri, Oct 31 - Tue, Nov 4

6:00 am - 7:00 amDCA-MDW

2h 00mnonstop

11:25 am - 4:10 pmMDW-DCA

3h 45m1 stop

$229Southwest

Find Deal

Mon, Nov 24 - Tue, Dec 2

9:35 pm - 10:35 pmDCA-MDW

2h 00mnonstop

10:05 am - 1:00 pmMDW-DCA

1h 55mnonstop

$233Southwest

Find Deal

Fri, Oct 31 - Mon, Nov 3

11:55 am - 1:00 pmDCA-MDW

2h 05mnonstop

8:10 pm - 10:55 pmMDW-DCA

1h 45mnonstop

$236Southwest

Find Deal

Sat, Nov 1 - Tue, Nov 4

6:00 am - 7:00 amDCA-MDW

2h 00mnonstop

7:30 am - 10:15 amMDW-DCA

1h 45mnonstop

$237Southwest

Find Deal

Thu, Dec 25 - Wed, Jan 7

6:55 pm - 8:00 pmDCA-MDW

2h 05mnonstop

10:15 am - 6:00 pmMDW-DCA

6h 45m2 stops

$238Southwest

Find Deal

Mon, Nov 24 - Tue, Dec 2

9:05 am - 10:15 amDCA-MDW

2h 10mnonstop

11:25 am - 4:10 pmMDW-DCA

3h 45m1 stop

$239Southwest

Find Deal

Fri, Oct 31 - Mon, Nov 3

2:55 pm - 3:55 pmDCA-MDW

2h 00mnonstop

11:25 am - 4:10 pmMDW-DCA

3h 45m1 stop

$242Southwest

Find Deal

Sat, Nov 1 - Tue, Nov 4

6:45 pm - 7:45 pmDCA-MDW

2h 00mnonstop

11:25 am - 4:10 pmMDW-DCA

3h 45m1 stop

$243Southwest

Find Deal

Sat, Nov 8 - Sat, Nov 15

11:25 am - 12:25 pmDCA-MDW

2h 00mnonstop

6:25 am - 1:55 pmMDW-DCA

6h 30m1 stop

$247Southwest

Find Deal

Useful Info

Low season	February
High season	May
Cheapest flight	$105
Average price round-trip	$299
Good deal one-way	$160

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 8% lower on average.

Flight from Reagan Washington National Airport to Chicago Midway Airport

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from Washington, D.C. Reagan-National Airport to Chicago

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Washington, D.C. Reagan-National Airport to Chicago?
With an average price of $313 return, Southwest is not the cheapest airline to fly from Washington, D.C. Reagan-National Airport to Chicago with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $207 on average.
What is the cheapest Southwest flight from Washington, D.C. Reagan-National Airport to Chicago?
In the last 3 days, the lowest price for a flight with Southwest from Washington, D.C. Reagan-National Airport to Chicago was $194 for a return flight and $105 for a one-way flight.
Does Southwest fly direct to Chicago from Washington, D.C. Reagan-National Airport?
Yes, Southwest does offer direct flights for the route, with around 34 flights per week.
What’s the cheapest day of the week to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest?
On average, the cheapest day of the week to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest is Friday, when prices are around $78. The most expensive day is generally Saturday, where the average price is around $114.
What’s the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest?
The cheapest month for Southwest flights to Chicago from Washington, D.C. Reagan-National Airport is generally August, where plane tickets cost $111 on average. If possible, try to avoid the most expensive months of May and January, where tickets cost $264 and $322 respectively.

8.0

Very good4,236 verified ratings

8.0Comfort

7.5Entertainment

7.0Food

8.1Boarding

8.6Crew

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

Gerald, Oct 2025

SJC-PDX

Boarding quick & efficient. Crew was friendly. Arrived early

6.0 Okay

Hung, Oct 2025

PHX-ABQ

mandatory demand customer to check their carry on because not enough people check bags.

8.0 Very good

Annette, Oct 2025

MCI-LGA

Good non stop is always good

10.0 Wonderful

Gabriel, Sep 2025

DEN-SMF

Connecting flight is on time and boarding was a breeze!

10.0 Wonderful

Gabriel, Sep 2025

LGA-DEN

Easy boarding process. No delays!

10.0 Wonderful

Melissa, Sep 2025

MDW-DTW

Excellent

10.0 Wonderful

Melissa, Sep 2025

MSY-MDW

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

10.0 Wonderful

Robert, Sep 2025

RNO-LAS

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

4.0 Mediocre

Ashish, Sep 2025

PHX-OGG

Southwest airlines boarding process is the worst. Period.

8.0 Very good

Verified traveler, Sep 2025

LAS-DTW

Good

Everything you need to know for your flight from Washington, D.C. Reagan-National Airport to Chicago

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$105 Find Cheap Southwest Flights from Washington, D.C. Reagan-National Airport to Chicago

Search hundreds of travel sites at once for deals on Southwest flights from Washington, D.C. Reagan-National Airport to Chicago

Cheap Southwest Flight Deals from Washington, D.C. Reagan-National Airport to Chicago

Recent round-trip Southwest flight deals from Washington, D.C. Reagan-National Airport to Chicago

Recent one-way Southwest flight deals from Washington, D.C. Reagan-National Airport to Chicago

Recent last minute Southwest flight deals from Washington, D.C. Reagan-National Airport to Chicago

Recent direct Southwest flight deals from Washington, D.C. Reagan-National Airport to Chicago

Good to know

When to Book Flights with Southwest from Washington, D.C. Reagan-National Airport to Chicago

FAQs for flying to Chicago with Southwest

Is Southwest the cheapest airline to fly with from Washington, D.C. Reagan-National Airport to Chicago?

What is the cheapest Southwest flight from Washington, D.C. Reagan-National Airport to Chicago?

Does Southwest fly direct to Chicago from Washington, D.C. Reagan-National Airport?

What’s the cheapest day of the week to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest?

What’s the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago with Southwest?

Southwest Customer Reviews

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Everything you need to know for your flight from Washington, D.C. Reagan-National Airport to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.