What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Washington, D.C. according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Washington, D.C. to Chicago?

Flights via Atlanta (ATL) offer the lowest average round-trip price of $168.

How many flights depart from Washington, D.C. to Chicago on average per week?

As of September 2025, 686 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.

Which layover airport has the shortest connection time from Washington, D.C. to Chicago?

Detroit (DTW) has the shortest average layover time for this route: 0h 45m.

Which layover airport has the shortest travel time from Washington, D.C. to Chicago?

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 40m.

How long does it take to fly to Chicago?

Average flight duration from Washington, D.C. to Chicago depends on which airport you fly into and out of. Flying from Washington, D.C. to Chicago O'Hare Intl Airport is 2h on average, while flying from Baltimore to Chicago O'Hare Intl Airport is 2h 02m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

Which airport is the most popular layover for flights between Washington, D.C. and Chicago?

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

How many flights depart from Washington, D.C. to Chicago on average per day?

As of September 2025, there are 98 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 6:00AM, with 42% of flights taking off at noon.

What is the cheapest airline that flies from Washington, D.C. to Chicago?

Frontier, American Airlines, and Spirit Airlines are the most popular carriers operating from Washington, D.C. to Chicago

Is flying the fastest way to get from Washington, D.C. to Chicago?

The quickest way is to book a flight from Washington, D.C. to Chicago, which can be as quick as 1h 55m onboard Southwest. You can also get a train from Washington, D.C. to Chicago, or a bus from Washington, D.C. to Chicago which can take you longer to arrive at your destination.

Is flying the cheapest way to get from Washington, D.C. to Chicago?

The cheapest way is to get a flight from Washington, D.C. to Chicago, which can be as cheap as $107. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $184. A bus from Washington, D.C. to Chicago is also an option, with an average price of $132.

When did momondo last update prices for flights from Washington, D.C. to Chicago?

Prices for flights from Washington, D.C. to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Washington, D.C. to Chicago?

There are 6 operators available for flights from Washington, D.C. to Chicago as of September 2025.

How old do you have to be to fly from Washington, D.C. to Chicago?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$69 Cheap Flights from Washington, D.C. to Chicago in 2025

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Find the cheapest flights from Washington, D.C. to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

4:06 pm - 5:15 pmBWI-MDW

2h 09mnonstop

12:25 pm - 3:21 pmMDW-BWI

1h 56mnonstop

$107Frontier

Find Deal

Sat, Nov 22 - Sun, Nov 23

4:15 pm - 10:03 pmBWI-MDW

6h 48m1 stop

5:40 am - 8:36 amMDW-BWI

1h 56mnonstop

$108Frontier

Find Deal

Thu, Oct 30 - Sun, Nov 2

6:05 am - 7:05 amBWI-MDW

2h 00mnonstop

7:40 pm - 10:30 pmMDW-BWI

1h 50mnonstop

$117Southwest

Find Deal

Wed, Oct 8 - Wed, Oct 8

10:35 am - 11:50 amBWI-ORD

2h 15mnonstop

1:30 pm - 4:25 pmORD-BWI

1h 55mnonstop

$117Southwest

Find Deal

Wed, Oct 1 - Sat, Oct 4

6:00 am - 7:16 amBWI-ORD

2h 16mnonstop

8:20 am - 11:20 amORD-BWI

2h 00mnonstop

$118American Airlines

Find Deal

Sat, Oct 25 - Sat, Nov 1

9:57 am - 11:10 amBWI-ORD

2h 13mnonstop

6:10 am - 9:02 amORD-BWI

1h 52mnonstop

$119Spirit Airlines

Find Deal

Thu, Sep 25 - Thu, Oct 2

7:10 pm - 8:24 pmBWI-ORD

2h 14mnonstop

5:05 am - 7:17 pmORD-BWI

13h 12m1 stop

$126Spirit Airlines

Find Deal

Fri, Nov 7 - Tue, Nov 11

10:51 am - 12:05 pmBWI-ORD

2h 14mnonstop

6:15 pm - 9:22 pmORD-BWI

2h 07mnonstop

$133United Airlines

Find Deal

Wed, Oct 1 - Fri, Oct 3

6:00 am - 10:38 amDCA-ORD

5h 38m1 stop

7:40 pm - 10:43 pmORD-DCA

2h 03mnonstop

$143United Airlines

Find Deal

Wed, Oct 1 - Wed, Oct 1

12:25 pm - 1:42 pmDCA-ORD

2h 17mnonstop

9:06 pm - 11:59 pmORD-DCA

1h 53mnonstop

$148American Airlines

Find Deal

Tue, Sep 30 - Sat, Oct 4

Spirit Airlines flights from Washington, D.C. to Chicago

Our best Spirit Airlines deals on Washington, D.C. to Chicago flight tickets

Spirit Airlines

Sep 25

BWI9:57 amBaltimore/Washington

2h 13m

ORD11:10 amChicago O'Hare Intl

Oct 2

ORD6:10 amChicago O'Hare Intl

1h 52m

BWI9:02 amBaltimore/Washington

$119

Find similar

Spirit Airlines

Nov 7

BWI7:10 pmBaltimore/Washington

2h 14m

ORD8:24 pmChicago O'Hare Intl

Nov 11

ORD5:05 amChicago O'Hare Intl

13h 12m

1 stop

BWI7:17 pmBaltimore/Washington

$126

Find similar

Spirit Airlines

Oct 2

BWI9:57 amBaltimore/Washington

2h 13m

ORD11:10 amChicago O'Hare Intl

Oct 6

ORD7:43 pmChicago O'Hare Intl

14h 18m

1 stop

BWI11:01 amBaltimore/Washington

$130

Find similar

Southwest flights from Washington, D.C. to Chicago

Our best Southwest deals on Washington, D.C. to Chicago flight tickets

Southwest

Oct 1

BWI10:35 amBaltimore/Washington

2h 15m

ORD11:50 amChicago O'Hare Intl

Oct 4

ORD1:30 pmChicago O'Hare Intl

1h 55m

BWI4:25 pmBaltimore/Washington

$117

Find similar

Southwest

Oct 21

BWI6:05 amBaltimore/Washington

2h 00m

MDW7:05 amChicago Midway

Oct 21

MDW7:40 pmChicago Midway

1h 50m

BWI10:30 pmBaltimore/Washington

$129

Find similar

Southwest

Nov 1

BWI8:00 pmBaltimore/Washington

2h 00m

MDW9:00 pmChicago Midway

Nov 3

MDW6:40 amChicago Midway

1h 50m

BWI9:30 amBaltimore/Washington

$133

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 11/22

4:06 pm-5:15 pm

Nonstop2h 09m

Chicago Midway

Sun 11/23

12:25 pm-3:21 pm

Nonstop1h 56m

$107

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 10/30

4:15 pm-10:03 pm

1 stop6h 48m

Chicago Midway

Sun 11/2

5:40 am-8:36 am

Nonstop1h 56m

$108

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 10/8

6:05 am-7:05 am

Nonstop2h 00m

Chicago Midway

Wed 10/8

7:40 pm-10:30 pm

Nonstop1h 50m

$117

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 10/1

10:35 am-11:50 am

Nonstop2h 15m

Chicago O'Hare Intl

Sat 10/4

1:30 pm-4:25 pm

Nonstop1h 55m

$117

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 10/25

6:00 am-7:16 am

Nonstop2h 16m

Chicago O'Hare Intl

Sat 11/1

8:20 am-11:20 am

Nonstop2h 00m

$118

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 9/25

9:57 am-11:10 am

Nonstop2h 13m

Chicago O'Hare Intl

Thu 10/2

6:10 am-9:02 am

Nonstop1h 52m

$119

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Fri 11/7

7:10 pm-8:24 pm

Nonstop2h 14m

Chicago O'Hare Intl

Tue 11/11

5:05 am-7:17 pm

1 stop13h 12m

$126

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 10/1

10:51 am-12:05 pm

Nonstop2h 14m

Chicago O'Hare Intl

Fri 10/3

6:15 pm-9:22 pm

Nonstop2h 07m

$133

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 10/1

6:00 am-10:38 am

1 stop5h 38m

Chicago O'Hare Intl

Wed 10/1

7:40 pm-10:43 pm

Nonstop2h 03m

$143

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 9/30

12:25 pm-1:42 pm

Nonstop2h 17m

Chicago O'Hare Intl

Sat 10/4

9:06 pm-11:59 pm

Nonstop1h 53m

$148

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How to get the cheapest flight ticket from Washington, D.C. to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $201. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Washington, D.C. to Chicago during January average around $229.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $386. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. to Chicago for around $501.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $334. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $437.

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

Fly from Baltimore/Washington to Chicago Midway for the best Washington, D.C. - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $325 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. for as low as $254 on momondo.

What cabin class options are available on Washington, D.C. to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Washington, D.C. to Chicago flights?

No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago.

How have Washington, D.C. to Chicago flight prices changed over time?

As of September 2025, prices for Washington, D.C. to Chicago flights are approximately 22% cheaper when compared to flights at the same time last year.

When to book flights from Washington, D.C. to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. to Chicago according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Washington, D.C. to Chicago (WAS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago

Best Price Found	$87
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is $87. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $139.

The fastest flight from Washington, D.C. to Chicago takes 1h 55m

Direct flights go from Washington, D.C. to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

Is flying the fastest way to get from Washington, D.C. to Chicago?
The quickest way is to book a flight from Washington, D.C. to Chicago, which can be as quick as 1h 55m onboard Southwest. You can also get a train from Washington, D.C. to Chicago, or a bus from Washington, D.C. to Chicago which can take you longer to arrive at your destination.
Is flying the cheapest way to get from Washington, D.C. to Chicago?
The cheapest way is to get a flight from Washington, D.C. to Chicago, which can be as cheap as $107. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $184. A bus from Washington, D.C. to Chicago is also an option, with an average price of $132.
How far is Washington, D.C. to Chicago by plane?
The straight-line distance from Washington, D.C. to Chicago is 593.1 mi. 1h 55m is a normal flight duration for this route.
When did momondo last update prices for flights from Washington, D.C. to Chicago?
Prices for flights from Washington, D.C. to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Washington, D.C. to Chicago?
There are 6 operators available for flights from Washington, D.C. to Chicago as of September 2025.
How old do you have to be to fly from Washington, D.C. to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Washington, D.C. to Chicago is Boeing 737-800, representing 11.41% of all bookings. The subsequent popular models are Airbus A320-100/200 at 10.57%, Airbus A319 at 9.51%, and Airbus A320neo at 9.11%.
What is the most popular airline from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked airline on the route from Washington, D.C. to Chicago is United Airlines, representing 28% of all bookings. The subsequent popular airlines are Southwest at 27%, Frontier at 25%, and American Airlines at 19%.

Best airlines flying from Washington, D.C. to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $46	Free Cancellation	Rating 6.3 8,023 reviews	Search Spirit Airlines flights
Frontier	PriceFrom $61	Free Cancellation	Rating 5.8 3,177 reviews	Search Frontier flights
Delta	PriceFrom $98	Free Cancellation	Rating 7.9 7,960 reviews	Search Delta flights
Southwest	PriceFrom $157	Free Cancellation	Rating 8.0 4,248 reviews	Search Southwest flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 8,937 reviews	Search United Airlines flights
American Airlines	PriceFrom $159	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Southwest Flights From Washington, D.C. to Chicago
Southwest flies from Washington, D.C. to Chicago around 32 times per week, with 4,248 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $157 (round-trip), much lower than the average airfare cost of $296 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. to Chicago
The best United Airlines deal for Washington, D.C. to Chicago flight tickets found on momondo in the last 72 hours was $158, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $326 round-trip. United Airlines operates 89 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 8,937 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

It is quick and easy to find Washington, D.C. to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

Flights from Washington, D.C. to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Washington, D.C. to Chicago?

Once you have performed a search for Washington, D.C. to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Cheap flights from Washington, D.C. to Chicago from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. to Chicago departing on 9/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Spirit Airlines flights from Washington, D.C. to Chicago

Our best Spirit Airlines deals on Washington, D.C. to Chicago flight tickets

Southwest flights from Washington, D.C. to Chicago

Our best Southwest deals on Washington, D.C. to Chicago flight tickets

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Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Washington, D.C. to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

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

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $334. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $437.

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

Fly from Baltimore/Washington to Chicago Midway for the best Washington, D.C. - Chicago flight prices

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

What cabin class options are available on Washington, D.C. to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Washington, D.C. to Chicago flights?

No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago.

How have Washington, D.C. to Chicago flight prices changed over time?

As of September 2025, prices for Washington, D.C. to Chicago flights are approximately 22% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Washington, D.C. to Chicago?

Frontier, American Airlines, and Spirit Airlines are the most popular carriers operating from Washington, D.C. to Chicago

What airlines fly to Chicago?

Which airport is the most popular layover for flights between Washington, D.C. and Chicago?

Atlanta (ATL) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Washington, D.C. to Chicago?

Flights via Atlanta (ATL) offer the lowest average round-trip price of $168.

Which layover airport has the shortest travel time from Washington, D.C. to Chicago?

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 40m.

Which layover airport has the shortest connection time from Washington, D.C. to Chicago?

Detroit (DTW) has the shortest average layover time for this route: 0h 45m.

How many flights depart from Washington, D.C. to Chicago on average per day?

As of September 2025, there are 98 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 6:00AM, with 42% of flights taking off at noon.

How many flights depart from Washington, D.C. to Chicago on average per week?

As of September 2025, 686 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Thu, with 17% of weekly flights taking off on this day.

How long does it take to fly to Chicago?

When to book flights from Washington, D.C. to Chicago

Cheap Washington, D.C. to Chicago (WAS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Is flying the fastest way to get from Washington, D.C. to Chicago?

Is flying the cheapest way to get from Washington, D.C. to Chicago?

How far is Washington, D.C. to Chicago by plane?

When did momondo last update prices for flights from Washington, D.C. to Chicago?

How many operators does momondo search for flights from Washington, D.C. to Chicago?

How old do you have to be to fly from Washington, D.C. to Chicago?

What documentation or ID do you need to fly to Chicago?

What is the most popular plane model from Washington, D.C. to Chicago?

What is the most popular airline from Washington, D.C. to Chicago?

Best airlines flying from Washington, D.C. to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. to Chicago with momondo

Southwest Flights From Washington, D.C. to Chicago

United Airlines Flights From Washington, D.C. to Chicago

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Washington, D.C. to Chicago?

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip