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

Flights via New York (JFK) offer the lowest average round-trip price of $152.

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

New York (JFK) was the most common stop: 75% of momondo users choosing 1-stop flights on this route connected there.

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

United Airlines, Southwest, and Delta are the most popular carriers operating from Washington, D.C. Reagan-National to Chicago

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

Detroit (DTW) has the shortest average layover time for this route: 1h 35m.

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. Reagan-National Airport according to our data. United Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 4h 52m.

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

The number of operators available for flights from Washington, D.C. Reagan-National Airport to Chicago is 4 as of March 2026.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Reagan-National Airport 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.

$103 Cheap Flights from Washington, D.C. Reagan-National Airport to Chicago in 2026

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

Prices are currently low for flights on this route. Typical prices usually range from $472 to $282. The lowest price recently found on this route was $212.

Q: How many flights depart from Washington, D.C. Reagan-National Airport to Chicago on average per day?

As of March 2026, there are 43 flights per day flying from Washington, D.C. Reagan-National Airport to Chicago. The most common time of day flights depart is 3:00PM, with 41% of flights taking off in the afternoon.

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Find the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 pm - 8:37 pm

DCA

ORD

27h 37m

1 stop

9:42 pm - 9:58 pm

ORD

DCA

23h 16m

1 stop

$212Frontier

Fri, May 8 - Mon, May 11

1:00 pm - 1:19 pm

DCA

ORD

25h 19m

1 stop

10:55 am - 9:59 pm

ORD

DCA

10h 04m

1 stop

$215Frontier

Thu, Apr 9 - Thu, Apr 16

7:25 am - 2:05 pm

DCA

MDW

7h 40m

1 stop

11:00 am - 1:50 pm

MDW

DCA

1h 50mnonstop

$215Southwest

Wed, Apr 22 - Sat, Apr 25

12:15 pm - 2:45 pm

DCA

MDW

3h 30m

1 stop

1:55 pm - 6:40 pm

MDW

DCA

3h 45m

1 stop

$216Southwest

Sat, May 9 - Tue, May 12

7:00 am - 8:37 pm

DCA

ORD

14h 37m

1 stop

9:42 pm - 4:59 pm

ORD

DCA

18h 17m

1 stop

$216Frontier

Tue, May 12 - Thu, May 21

11:45 am - 12:45 pm

DCA

MDW

2h 00mnonstop

7:45 am - 6:25 pm

MDW

DCA

9h 40m

2 stops

$219Southwest

Tue, Apr 14 - Sat, Apr 18

5:55 am - 7:24 am

DCA

ORD

2h 29mnonstop

5:58 pm - 8:59 pm

ORD

DCA

2h 01mnonstop

$221American Airlines

Wed, May 20 - Tue, May 26

6:30 am - 7:46 am

DCA

ORD

2h 16mnonstop

6:00 pm - 9:06 pm

ORD

DCA

2h 06mnonstop

$223United Airlines

Thu, Apr 23 - Mon, May 4

2:00 pm - 7:23 pm

DCA

ORD

6h 23m

1 stop

7:10 am - 2:56 pm

ORD

DCA

6h 46m

1 stop

$224Delta

Sat, Apr 18 - Wed, Apr 22

6:05 am - 8:43 am

DCA

MDW

3h 38m

1 stop

1:22 pm - 6:59 pm

MDW

DCA

4h 37m

1 stop

$224Delta

Sat, May 9 - Tue, May 12

American Airlines flights from Washington, D.C. Reagan-National Airport to Chicago

Our best American Airlines deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets

American Airlines

May 20

DCA5:55 amWashington, D.C. Reagan-National

2h 29m

ORD7:24 amChicago O'Hare Intl

May 26

ORD5:58 pmChicago O'Hare Intl

2h 01m

DCA8:59 pmWashington, D.C. Reagan-National

$221

American Airlines

Apr 22

DCA10:30 amWashington, D.C. Reagan-National

5h 12m

1 stop

ORD2:42 pmChicago O'Hare Intl

May 5

ORD11:40 amChicago O'Hare Intl

2h 00m

DCA2:40 pmWashington, D.C. Reagan-National

$237

American Airlines

Apr 15

DCA3:15 pmWashington, D.C. Reagan-National

2h 30m

ORD4:45 pmChicago O'Hare Intl

Apr 18

ORD9:55 amChicago O'Hare Intl

2h 00m

DCA12:55 pmWashington, D.C. Reagan-National

$238

Frontier flights from Washington, D.C. Reagan-National Airport to Chicago

Our best Frontier deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets

Frontier

May 8

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

27h 37m

1 stop

ORD8:37 pmChicago O'Hare Intl

May 11

ORD9:42 pmChicago O'Hare Intl

23h 16m

1 stop

DCA9:58 pmWashington, D.C. Reagan-National

$212

Frontier

Apr 9

DCA1:00 pmWashington, D.C. Reagan-National

25h 19m

1 stop

ORD1:19 pmChicago O'Hare Intl

Apr 16

ORD10:55 amChicago O'Hare Intl

10h 04m

1 stop

DCA9:59 pmWashington, D.C. Reagan-National

$215

Frontier

May 12

DCA7:00 amWashington, D.C. Reagan-National

14h 37m

1 stop

ORD8:37 pmChicago O'Hare Intl

May 21

ORD9:42 pmChicago O'Hare Intl

18h 17m

1 stop

DCA4:59 pmWashington, D.C. Reagan-National

$216

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 5/8

6:00 pm-8:37 pm

1 stop27h 37m

Chicago O'Hare Intl

Mon 5/11

9:42 pm-9:58 pm

1 stop23h 16m

$212

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 4/9

1:00 pm-1:19 pm

1 stop25h 19m

Chicago O'Hare Intl

Thu 4/16

10:55 am-9:59 pm

1 stop10h 04m

$215

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/22

7:25 am-2:05 pm

1 stop7h 40m

Chicago Midway

Sat 4/25

11:00 am-1:50 pm

Nonstop1h 50m

$215

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/9

12:15 pm-2:45 pm

1 stop3h 30m

Chicago Midway

Tue 5/12

1:55 pm-6:40 pm

1 stop3h 45m

$216

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 5/12

7:00 am-8:37 pm

1 stop14h 37m

Chicago O'Hare Intl

Thu 5/21

9:42 pm-4:59 pm

1 stop18h 17m

$216

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/14

11:45 am-12:45 pm

Nonstop2h 00m

Chicago Midway

Sat 4/18

7:45 am-6:25 pm

2 stops9h 40m

$219

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 5/20

5:55 am-7:24 am

Nonstop2h 29m

Chicago O'Hare Intl

Tue 5/26

5:58 pm-8:59 pm

Nonstop2h 01m

$221

Quickest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 4/23

6:30 am-7:46 am

Nonstop2h 16m

Chicago O'Hare Intl

Mon 5/4

6:00 pm-9:06 pm

Nonstop2h 06m

$223

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 4/18

2:00 pm-7:23 pm

1 stop6h 23m

Chicago O'Hare Intl

Wed 4/22

7:10 am-2:56 pm

1 stop6h 46m

$224

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/9

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

Tue 5/12

1:22 pm-6:59 pm

1 stop4h 37m

$224

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. Reagan-National Airport 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. Reagan-National Airport and Chicago?

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. Reagan-National Airport, with most prices found around $279. If you’re not able to fly to Chicago in September, then July is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during July average around $285.

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 $384. 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. Reagan-National Airport to Chicago for around $512.

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. Reagan-National Airport to Chicago during this time can be as low as $377. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $422.

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

Fly from Washington, D.C. Reagan-National to Chicago O'Hare Intl for the best Washington, D.C. Reagan-National - 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. Reagan-National Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $324 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. Reagan-National Airport for as low as $272 on momondo.

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

There are 4 cabin classes available to choose from on Washington, D.C. Reagan-National 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. Reagan-National Airport to Chicago flights?

You could potentially save up to 7% on your flight if you consider stops on a Washington, D.C. Reagan-National Airport to Chicago flight.

How have Washington, D.C. Reagan-National Airport to Chicago flight prices changed over time?

As of March 2026, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 42% more expensive when compared to flights at the same time last year.

When to book flights from Washington, D.C. Reagan-National Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. Reagan-National Airport 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. Reagan-National Airport to Chicago (DCA to CHI) flight deals and tips

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

Best Price Found	$198
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. Reagan-National Airport in the past 72 hours is $198. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $305.

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

Direct flights go from Washington, D.C. Reagan-National Airport to Chicago every day.

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

Search flight deals

How far is Washington, D.C. Reagan-National to Chicago by plane?
There are 594.5 mi between Washington, D.C. Reagan-National and Chicago. Typically, this will take 1h 55m by plane in normal conditions.
When did momondo last update prices for flights from Washington, D.C. Reagan-National Airport to Chicago?
Prices for flights from Washington, D.C. Reagan-National Airport to Chicago refresh daily.
How many operators does momondo search for flights from Washington, D.C. Reagan-National Airport to Chicago?
The number of operators available for flights from Washington, D.C. Reagan-National Airport to Chicago is 4 as of March 2026.
How old do you have to be to fly from Washington, D.C. Reagan-National Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Reagan-National Airport 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. Reagan-National Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Washington, D.C. Reagan-National Airport to Chicago is Airbus A319 (15.71% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (13.98%), Boeing 737-800 (13.22%), and Boeing 737-900 (6.59%).
What is the most popular airline from Washington, D.C. Reagan-National Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Washington, D.C. Reagan-National Airport to Chicago is Southwest (34% of total bookings). The next most popular airlines are American Airlines (33%), United Airlines (32%), and Frontier (1%).

Best airlines flying from Washington, D.C. Reagan-National Airport to Chicago

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

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $29	Free Cancellation	Rating 5.7 3,015 reviews	Search Frontier flights
American Airlines	PriceFrom $166	Free Cancellation	Rating 7.1 11,496 reviews	Search American Airlines flights
Southwest	PriceFrom $187	Free Cancellation	Rating 8.0 4,333 reviews	Search Southwest flights
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 9,488 reviews	Search United Airlines flights

Southwest Flights From Washington, D.C. Reagan-National Airport to Chicago
Southwest flies from Washington, D.C. Reagan-National Airport to Chicago around 32 times per week, with 4,333 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. Reagan-National Airport to Chicago in the last 72 hours was $187 (round-trip), much lower than the average airfare cost of $309 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. Reagan-National Airport to Chicago
United Airlines (7.4/10 from 9,488 reviews) operates around 58 flights from Washington, D.C. Reagan-National Airport to Chicago in any given week. The average United Airlines airfare for this route is around $343, with deals from around $209 rare but found on momondo. Referenced prices are for round-trip Washington, D.C. Reagan-National Airport to Chicago flight searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Washington, D.C. to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

momondo does allow users to show only those flights to Chicago from Washington, D.C. which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Chicago from Washington, D.C.. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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. Reagan-National Airport to Chicago from $102

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American Airlines flights from Washington, D.C. Reagan-National Airport to Chicago

Our best American Airlines deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets

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Our best Frontier deals on Washington, D.C. Reagan-National Airport 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. Reagan-National Airport to Chicago

What is the typical price of a round-trip flight between Washington, D.C. Reagan-National Airport 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. Reagan-National to Chicago flight route?

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

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

Can stopping save me money on Washington, D.C. Reagan-National Airport to Chicago flights?

How have Washington, D.C. Reagan-National Airport to Chicago flight prices changed over time?

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

What airlines fly to Chicago?

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

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

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

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

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

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

When to book flights from Washington, D.C. Reagan-National Airport to Chicago

Cheap Washington, D.C. Reagan-National Airport to Chicago (DCA to CHI) flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

Best airlines flying from Washington, D.C. Reagan-National Airport to Chicago

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

Southwest Flights From Washington, D.C. Reagan-National Airport to Chicago

United Airlines Flights From Washington, D.C. Reagan-National Airport to Chicago

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Airports listed have a maximum distance of 78.5 mi from Chicago

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