How far in advance should I book tickets for a flight with Southwest from Chicago to Washington, D.C.?

Generally, when trying to get a below average price for your ticket, try to book around 22 days before departure. For the cheapest possible price, our data suggests booking 67 days before departure.

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

With an average price of $304 return, Southwest is not the cheapest airline to fly from Chicago to Washington, D.C. with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $216 on average.

What is the cheapest Southwest flight from Chicago to Washington, D.C.?

In the last 3 days, the lowest price for a flight with Southwest from Chicago to Washington, D.C. was $89 for a return flight and $48 for a one-way flight.

Does Southwest fly direct to Washington, D.C. from Chicago?

Yes, Southwest does offer direct flights for the route, with around 7 flights per week.

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

On average, the cheapest day of the week to fly from Chicago to Washington, D.C. with Southwest is Monday, when prices are around $69. The most expensive day is generally Saturday, where the average price is around $114.

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

The cheapest month for Southwest flights to Washington, D.C. from Chicago is generally February, where plane tickets cost $108 on average. If possible, try to avoid the most expensive months of March and December, where tickets cost $175 and $175 respectively.

$70 Cheap Southwest Flights from Chicago to Washington, D.C.

Flight Deals

Cheap Southwest Flight Deals from Chicago to Washington, D.C.

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Chicago to Washington, D.C. 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 Chicago to Washington, D.C.

Mon, Jan 12 - Wed, Jan 14

5:15 pm - 8:10 pmMDW-BWI

1h 55mnonstop

10:25 am - 11:35 amBWI-MDW

2h 10mnonstop

$139Southwest

Find Deal

Tue, Jan 20 - Fri, Jan 23

5:15 pm - 8:10 pmMDW-BWI

1h 55mnonstop

10:25 am - 11:35 amBWI-MDW

2h 10mnonstop

$148Southwest

Find Deal

Fri, Jan 23 - Sun, Jan 25

1:15 pm - 4:00 pmMDW-BWI

1h 45mnonstop

8:15 pm - 9:25 pmBWI-MDW

2h 10mnonstop

$157Southwest

Find Deal

Wed, Dec 17 - Tue, Jan 6

6:55 pm - 9:45 pmMDW-BWI

1h 50mnonstop

5:50 pm - 7:00 pmBWI-MDW

2h 10mnonstop

$158Southwest

Find Deal

Wed, Nov 19 - Wed, Dec 3

6:40 am - 9:30 amMDW-BWI

1h 50mnonstop

8:00 pm - 9:05 pmBWI-MDW

2h 05mnonstop

$168Southwest

Find Deal

Thu, Dec 25 - Thu, Jan 1

6:55 pm - 9:45 pmMDW-BWI

1h 50mnonstop

12:40 pm - 1:45 pmBWI-MDW

2h 05mnonstop

$169Southwest

Find Deal

Thu, Nov 27 - Thu, Dec 4

2:30 pm - 5:15 pmMDW-BWI

1h 45mnonstop

4:45 pm - 5:50 pmBWI-MDW

2h 05mnonstop

$173Southwest

Find Deal

Wed, Dec 24 - Thu, Jan 1

12:55 pm - 3:40 pmMDW-BWI

1h 45mnonstop

11:20 am - 2:05 pmBWI-MDW

3h 45m1 stop

$175Southwest

Find Deal

Fri, Dec 5 - Sun, Dec 7

6:55 pm - 9:45 pmMDW-BWI

1h 50mnonstop

9:55 am - 11:00 amBWI-MDW

2h 05mnonstop

$177Southwest

Find Deal

Fri, Jan 9 - Sun, Jan 11

6:05 am - 2:55 pmORD-BWI

7h 50m2 stops

6:15 am - 2:45 pmBWI-ORD

9h 30m1 stop

$182Southwest

Find Deal

Useful Info

Low season	February
High season	November
Cheapest flight	$70
Average price round-trip	$257
Good deal one-way	$158

Best time to beat the crowds with an average 0% drop in price.

Most popular time to fly with an average 14% increase in price.

Flight from Chicago Midway Airport to Baltimore

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from Chicago to Washington, D.C.

Average price per month

Flight prices as travel date approaches

How far in advance should I book tickets for a flight with Southwest from Chicago to Washington, D.C.?
Generally, when trying to get a below average price for your ticket, try to book around 22 days before departure. For the cheapest possible price, our data suggests booking 67 days before departure.
Is Southwest the cheapest airline to fly with from Chicago to Washington, D.C.?
With an average price of $304 return, Southwest is not the cheapest airline to fly from Chicago to Washington, D.C. with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $216 on average.
What is the cheapest Southwest flight from Chicago to Washington, D.C.?
In the last 3 days, the lowest price for a flight with Southwest from Chicago to Washington, D.C. was $89 for a return flight and $48 for a one-way flight.
Does Southwest fly direct to Washington, D.C. from Chicago?
Yes, Southwest does offer direct flights for the route, with around 7 flights per week.
What’s the cheapest day of the week to fly from Chicago to Washington, D.C. with Southwest?
On average, the cheapest day of the week to fly from Chicago to Washington, D.C. with Southwest is Monday, when prices are around $69. The most expensive day is generally Saturday, where the average price is around $114.
What’s the cheapest month to fly from Chicago to Washington, D.C. with Southwest?
The cheapest month for Southwest flights to Washington, D.C. from Chicago is generally February, where plane tickets cost $108 on average. If possible, try to avoid the most expensive months of March and December, where tickets cost $175 and $175 respectively.

8.0

Very good4,243 verified ratings

8.0Comfort

7.5Entertainment

8.6Crew

8.1Boarding

7.0Food

Pros +

Cons -

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10.0 Wonderful

James, Oct 2025

TUS-LAS

Very good

8.0 Very good

Greg, Oct 2025

OAK-BUR

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 Very good

Margaret, Oct 2025

SAV-HOU

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 Very good

TODD, Oct 2025

CMH-HOU

Tried watching free movie and it kept freezing so I couldn’t finish.

10.0 Wonderful

Antonio, Oct 2025

PVD-MCO

Always reliable

10.0 Wonderful

Verified traveler, Oct 2025

MDW-BWI

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

4.0 Mediocre

Mike, Oct 2025

GRR-MDW

Staff/crew very good. 4 hour delay not good.

10.0 Wonderful

Stacy, Oct 2025

SMF-DEN

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Everything you need to know for your flight from Chicago to Washington, D.C.

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Southwest flights

Cabin class types available on flights from Chicago to Washington, D.C.

First Class flights from Chicago to Washington, D.C.

Business Class flights from Chicago to Washington, D.C.

Prem Econ Class flights from Chicago to Washington, D.C.

Economy Class flights from Chicago to Washington, D.C.

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CHI - WAS

$70 Find Cheap Southwest Flights from Chicago to Washington, D.C.

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

Cheap Southwest Flight Deals from Chicago to Washington, D.C.

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

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

Recent last minute Southwest flight deals from Chicago to Washington, D.C.

Recent direct Southwest flight deals from Chicago to Washington, D.C.

Good to know

When to Book Flights with Southwest from Chicago to Washington, D.C.

FAQs for flying to Washington, D.C. with Southwest

How far in advance should I book tickets for a flight with Southwest from Chicago to Washington, D.C.?

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

What is the cheapest Southwest flight from Chicago to Washington, D.C.?

Does Southwest fly direct to Washington, D.C. from Chicago?

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

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

Southwest Customer Reviews

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Everything you need to know for your flight from Chicago to Washington, D.C.

Cabin class types available on flights from Chicago to Washington, D.C.

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

Complete your trip to Washington, D.C. with a hotel stay or car rental

Flights to other popular destinations

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.

Find deals for your return flight

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.