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

As of August 2026, 444 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Mon, with 31% of weekly flights taking off on this day.

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

Atlanta (ATL) has the shortest average layover time for this route: 1h 54m.

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

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

What airlines fly to Chicago?

United Airlines, American Airlines and Frontier 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 54% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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: 69% 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 $142.

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

Flights connecting via New York (JFK) have the shortest average one-way travel time: 4h 57m.

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

As of August 2026, there are 63 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 46% of flights taking off at noon.

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 5 operators available for flights from Washington, D.C. to Chicago as of August 2026.

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.

$89 Cheap Flights from Washington, D.C. to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

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

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:20 am - 10:55 am-

5h 35m

6:25 am - 5:18 pm-

9h 53m

$189Frontier

Tue, Sep 8 - Wed, Sep 9

8:39 pm - 7:53 am-

12h 14m

9:20 am - 6:29 pm-

8h 09m

$190Frontier

Tue, Aug 25 - Thu, Aug 27

1:20 pm - 4:40 pm-

4h 20m

8:55 am - 3:55 pm-

6h 00m

$197Southwest

Sat, Sep 5 - Sun, Sep 6

1:20 pm - 4:40 pm-

4h 20m

3:10 pm - 10:45 pm-

6h 35m

$197Southwest

Sat, Sep 5 - Fri, Sep 11

9:40 am - 12:35 pm-

3h 55m

6:44 pm - 11:28 pm-

3h 44m

$197Delta

Thu, Nov 26 - Thu, Nov 26

12:33 pm - 4:59 pm-

5h 26m

5:03 pm - 11:02 pm-

4h 59m

$197Delta

Sat, Sep 5 - Fri, Sep 11

9:30 am - 10:47 am-

2h 17mnonstop

6:00 am - 8:55 am-

1h 55mnonstop

$200United Airlines

Thu, Sep 3 - Mon, Sep 7

3:30 pm - 4:52 pm-

2h 22mnonstop

6:00 am - 8:55 am-

1h 55mnonstop

$200United Airlines

Wed, Sep 2 - Mon, Sep 7

6:30 am - 7:58 am-

2h 28mnonstop

6:55 am - 9:59 am-

2h 04mnonstop

$216American Airlines

Fri, Sep 11 - Mon, Sep 14

6:30 am - 7:58 am-

2h 28mnonstop

7:47 am - 10:52 am-

2h 05mnonstop

$216American Airlines

Fri, Sep 11 - Mon, Sep 14

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Frontier flights from Washington, D.C. to Chicago

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

Frontier

Sep 8

IAD6:20 amWashington, D.C. Dulles Intl

5h 35m

1 stop

MDW10:55 amChicago Midway

Sep 9

MDW6:25 amChicago Midway

9h 53m

1 stop

IAD5:18 pmWashington, D.C. Dulles Intl

$189

Frontier

Sep 15

DCA6:00 pmWashington, D.C. Reagan-National

7h 23m

1 stop

ORD12:23 amChicago O'Hare Intl

Sep 16

ORD6:30 amChicago O'Hare Intl

28h 41m

1 stop

DCA12:11 pmWashington, D.C. Reagan-National

$190

Frontier

Aug 27

IAD6:20 amWashington, D.C. Dulles Intl

5h 35m

1 stop

MDW10:55 amChicago Midway

Aug 31

MDW6:05 amChicago Midway

10h 09m

1 stop

IAD5:14 pmWashington, D.C. Dulles Intl

$191

JetBlue flights from Washington, D.C. to Chicago

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

JetBlue

Aug 18

DCA6:00 amWashington, D.C. Reagan-National

8h 39m

1 stop

ORD1:39 pmChicago O'Hare Intl

Aug 19

ORD2:35 pmChicago O'Hare Intl

7h 57m

1 stop

DCA11:32 pmWashington, D.C. Reagan-National

$268

JetBlue

Aug 12

DCA3:20 pmWashington, D.C. Reagan-National

9h 24m

1 stop

ORD11:44 pmChicago O'Hare Intl

Aug 20

ORD2:35 pmChicago O'Hare Intl

7h 57m

1 stop

DCA11:32 pmWashington, D.C. Reagan-National

$296

JetBlue

Aug 17

DCA2:25 pmWashington, D.C. Reagan-National

6h 02m

1 stop

ORD7:27 pmChicago O'Hare Intl

Aug 18

ORD2:35 pmChicago O'Hare Intl

7h 57m

1 stop

DCA11:32 pmWashington, D.C. Reagan-National

$364

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Tue 9/8

6:20 am-10:55 am

1 stop5h 35m

Chicago Midway

Wed 9/9

6:25 am-5:18 pm

1 stop9h 53m

$189

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Tue 8/25

8:39 pm-7:53 am

1 stop12h 14m

Chicago O'Hare Intl

Thu 8/27

9:20 am-6:29 pm

1 stop8h 09m

$190

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 9/5

1:20 pm-4:40 pm

1 stop4h 20m

Chicago Midway

Sun 9/6

8:55 am-3:55 pm

1 stop6h 00m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 9/5

1:20 pm-4:40 pm

1 stop4h 20m

Chicago Midway

Fri 9/11

3:10 pm-10:45 pm

1 stop6h 35m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 11/26

9:40 am-12:35 pm

1 stop3h 55m

Chicago Midway

Thu 11/26

6:44 pm-11:28 pm

1 stop3h 44m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 9/5

12:33 pm-4:59 pm

1 stop5h 26m

Chicago Midway

Fri 9/11

5:03 pm-11:02 pm

1 stop4h 59m

$197

Quickest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 9/3

9:30 am-10:47 am

Nonstop2h 17m

Chicago O'Hare Intl

Mon 9/7

6:00 am-8:55 am

Nonstop1h 55m

$200

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/2

3:30 pm-4:52 pm

Nonstop2h 22m

Chicago O'Hare Intl

Mon 9/7

6:00 am-8:55 am

Nonstop1h 55m

$200

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 9/11

6:30 am-7:58 am

Nonstop2h 28m

Chicago O'Hare Intl

Mon 9/14

6:55 am-9:59 am

Nonstop2h 04m

$216

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 9/11

6:30 am-7:58 am

Nonstop2h 28m

Chicago O'Hare Intl

Mon 9/14

7:47 am-10:52 am

Nonstop2h 05m

$216

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 typical price of a round-trip flight between Washington, D.C. and Chicago?

Prices are currently typical for flights on this route.

Typical prices usually range from $189 to $347.
The lowest price recently found on this route was $189.

What is the cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $270. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Washington, D.C. to Chicago during September average around $275.

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 Saturday when prices can be found for as low as $400. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. to Chicago for around $534.

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 $409. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $456.

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

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

How far in advance should I book a flight from Washington, D.C. 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 $399 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 $284 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 August 2026, prices for Washington, D.C. to Chicago flights are approximately 23% 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	$177
Fastest flight time	1h 55m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is $177. The best round-trip flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is $271.

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 3 airports in Chicago. From Washington, D.C. there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying from Washington, D.C. to Chicago

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 5 operators available for flights from Washington, D.C. to Chicago as of August 2026.
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 MAX 8, representing 15.14% of all bookings. The subsequent popular models are Boeing 737-800 at 13.06%, Boeing 737-900 at 9.55%, and Airbus A319 at 9.07%.
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 31% of all bookings. The subsequent popular airlines are Southwest at 26%, Frontier at 23%, 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
Frontier	PriceFrom $29	Free Cancellation	Rating 5.6 2,737 reviews	Search Frontier flights
Southwest	PriceFrom $134	Free Cancellation	Rating 8.0 4,222 reviews	Search Southwest flights
Delta	PriceFrom $149	Free Cancellation	Rating 7.8 8,483 reviews	Search Delta flights
United Airlines	PriceFrom $161	Free Cancellation	Rating 7.4 10,059 reviews	Search United Airlines flights
American Airlines	PriceFrom $174	Free Cancellation	Rating 7.1 11,845 reviews	Search American Airlines flights

Southwest Flights From Washington, D.C. to Chicago
Southwest flies from Washington, D.C. to Chicago around 6 times per week, with 4,222 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $134 (round-trip), much lower than the average airfare cost of $340 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 $161, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $373 round-trip. United Airlines operates 82 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 10,059 United Airlines reviews by users on momondo have scored the airline at 7.4/10.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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 $89

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 9/24. 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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Frontier flights from Washington, D.C. to Chicago

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

JetBlue flights from Washington, D.C. to Chicago

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

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See travel insights to Chicago from

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

What is the typical price of a round-trip flight between Washington, D.C. and Chicago?

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?

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

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

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

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

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

What is the cheapest airline that flies 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?

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

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

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

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

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

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List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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