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

With an average price of $305 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 22 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 Thursday, where the average price is around $99.

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 September and January, where tickets cost $265 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

Tue, Oct 21 - Wed, Oct 22

9:05 am - 10:15 amDCA-MDW

2h 10mnonstop

10:15 am - 1:00 pmMDW-DCA

1h 45mnonstop

$209Southwest

Find Deal

Tue, Oct 21 - Wed, Oct 22

3:30 pm - 4:30 pmDCA-MDW

2h 00mnonstop

7:35 am - 12:50 pmMDW-DCA

4h 15m1 stop

$215Southwest

Find Deal

Mon, Nov 24 - Tue, Dec 2

9:05 am - 10:15 amDCA-MDW

2h 10mnonstop

10:05 am - 1:00 pmMDW-DCA

1h 55mnonstop

$223Southwest

Find Deal

Wed, Oct 29 - Thu, Oct 30

3:30 pm - 4:30 pmDCA-MDW

2h 00mnonstop

12:10 pm - 3:00 pmMDW-DCA

1h 50mnonstop

$224Southwest

Find Deal

Tue, Oct 21 - Wed, Oct 22

3:45 pm - 10:05 pmDCA-MDW

7h 20m2 stops

7:35 am - 12:50 pmMDW-DCA

4h 15m1 stop

$230Southwest

Find Deal

Sat, Nov 8 - Tue, Nov 11

11:25 am - 12:25 pmDCA-MDW

2h 00mnonstop

7:30 am - 10:15 amMDW-DCA

1h 45mnonstop

$233Southwest

Find Deal

Tue, Oct 21 - Wed, Oct 22

11:45 am - 9:30 pmDCA-ORD

10h 45m2 stops

1:30 pm - 8:50 pmORD-DCA

6h 20m1 stop

$234Southwest

Find Deal

Wed, Oct 29 - Mon, Nov 3

11:45 am - 12:50 pmDCA-MDW

2h 05mnonstop

11:25 am - 6:15 pmMDW-DCA

5h 50m1 stop

$234Southwest

Find Deal

Mon, Nov 24 - Thu, Nov 27

9:05 am - 10:15 amDCA-MDW

2h 10mnonstop

1:15 pm - 4:05 pmMDW-DCA

1h 50mnonstop

$237Southwest

Find Deal

Fri, Oct 31 - Mon, Nov 3

2:55 pm - 3:55 pmDCA-MDW

2h 00mnonstop

7:30 am - 10:15 amMDW-DCA

1h 45mnonstop

$238Southwest

Find Deal

Useful Info

Low season	February
High season	October
Cheapest flight	$105
Average price round-trip	$293
Good deal one-way	$150

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

Most popular time to fly and prices are also 2% 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 $305 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 $193 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 22 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 Thursday, where the average price is around $99.
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 September and January, where tickets cost $265 and $322 respectively.

8.0

Very good4,248 verified ratings

8.6Crew

8.1Boarding

8.0Comfort

7.5Entertainment

7.0Food

Pros +

Cons -

Show reviews that mention

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

10.0 Wonderful

Verified traveler, Sep 2025

CLT-BWI

Always liked SW

10.0 Wonderful

Lynda, Sep 2025

MDW-OKC

Clear communication

10.0 Wonderful

Lynda, Sep 2025

BNA-MDW

On time-smooth flights-clear communication

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.