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.

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

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

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 airlines fly to Chicago?

American Airlines, United 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. American 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 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.

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.

$85 Cheap Flights from Washington, D.C. Reagan-National Airport to Chicago in 2026

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

As of February 2026, there are 48 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 43% of flights taking off at noon.

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

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One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:20 am - 9:41 am

DCA

ORD

2h 21mnonstop

12:40 pm - 3:38 pm

ORD

DCA

1h 58mnonstop

$181United Airlines

Sat, Apr 25 - Mon, Apr 27

6:40 am - 7:45 am

DCA

MDW

2h 05mnonstop

4:20 pm - 7:10 pm

MDW

DCA

1h 50mnonstop

$194Southwest

Sat, Apr 18 - Wed, Apr 22

7:00 pm - 8:05 pm

DCA

MDW

2h 05mnonstop

8:15 am - 11:05 am

MDW

DCA

1h 50mnonstop

$197Southwest

Wed, Apr 29 - Wed, May 13

6:30 pm - 7:55 pm

DCA

ORD

2h 25mnonstop

7:40 pm - 10:43 pm

ORD

DCA

2h 03mnonstop

$197United Airlines

Tue, Mar 24 - Tue, Mar 31

3:15 pm - 4:45 pm

DCA

ORD

2h 30mnonstop

12:42 pm - 3:45 pm

ORD

DCA

2h 03mnonstop

$198American Airlines

Wed, Apr 8 - Wed, Apr 15

11:36 am - 12:58 pm

DCA

ORD

2h 22mnonstop

4:00 pm - 7:05 pm

ORD

DCA

2h 05mnonstop

$199American Airlines

Wed, Apr 8 - Wed, Apr 15

12:10 pm - 1:15 pm

DCA

MDW

2h 05mnonstop

5:30 am - 8:25 am

MDW

DCA

1h 55mnonstop

$200Southwest

Sat, Mar 14 - Tue, Mar 17

7:00 pm - 8:35 pm

DCA

ORD

2h 35mnonstop

9:01 pm - 11:59 pm

ORD

DCA

1h 58mnonstop

$201United Airlines

Sat, Mar 14 - Sat, Mar 21

8:00 am - 9:50 am

DCA

ORD

26h 50m

1 stop

10:50 am - 1:00 pm

ORD

DCA

25h 10m

1 stop

$202Frontier

Thu, Apr 16 - Sun, Apr 19

4:59 pm - 9:36 pm

DCA

ORD

5h 37m

1 stop

9:41 am - 4:42 pm

ORD

DCA

6h 01m

1 stop

$207JetBlue

Tue, Apr 14 - Wed, Apr 15

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

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

United Airlines

Apr 25

DCA8:20 amWashington, D.C. Reagan-National

2h 21m

ORD9:41 amChicago O'Hare Intl

Apr 27

ORD12:40 pmChicago O'Hare Intl

1h 58m

DCA3:38 pmWashington, D.C. Reagan-National

$181

United Airlines

Mar 24

DCA6:30 pmWashington, D.C. Reagan-National

2h 25m

ORD7:55 pmChicago O'Hare Intl

Mar 31

ORD7:40 pmChicago O'Hare Intl

2h 03m

DCA10:43 pmWashington, D.C. Reagan-National

$197

United Airlines

Mar 14

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

2h 35m

ORD8:35 pmChicago O'Hare Intl

Mar 21

ORD9:01 pmChicago O'Hare Intl

1h 58m

DCA11:59 pmWashington, D.C. Reagan-National

$201

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

Apr 8

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

2h 30m

ORD4:45 pmChicago O'Hare Intl

Apr 15

ORD12:42 pmChicago O'Hare Intl

2h 03m

DCA3:45 pmWashington, D.C. Reagan-National

$198

American Airlines

Apr 8

DCA11:36 amWashington, D.C. Reagan-National

2h 22m

ORD12:58 pmChicago O'Hare Intl

Apr 15

ORD4:00 pmChicago O'Hare Intl

2h 05m

DCA7:05 pmWashington, D.C. Reagan-National

$199

American Airlines

Apr 22

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

2h 29m

ORD7:24 amChicago O'Hare Intl

Apr 25

ORD4:00 pmChicago O'Hare Intl

2h 05m

DCA7:05 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

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 4/25

8:20 am-9:41 am

Nonstop2h 21m

Chicago O'Hare Intl

Mon 4/27

12:40 pm-3:38 pm

Nonstop1h 58m

$181

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 4/18

6:40 am-7:45 am

Nonstop2h 05m

Chicago Midway

Wed 4/22

4:20 pm-7:10 pm

Nonstop1h 50m

$194

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/29

7:00 pm-8:05 pm

Nonstop2h 05m

Chicago Midway

Wed 5/13

8:15 am-11:05 am

Nonstop1h 50m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 3/24

6:30 pm-7:55 pm

Nonstop2h 25m

Chicago O'Hare Intl

Tue 3/31

7:40 pm-10:43 pm

Nonstop2h 03m

$197

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 4/8

3:15 pm-4:45 pm

Nonstop2h 30m

Chicago O'Hare Intl

Wed 4/15

12:42 pm-3:45 pm

Nonstop2h 03m

$198

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 4/8

11:36 am-12:58 pm

Nonstop2h 22m

Chicago O'Hare Intl

Wed 4/15

4:00 pm-7:05 pm

Nonstop2h 05m

$199

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 3/14

12:10 pm-1:15 pm

Nonstop2h 05m

Chicago Midway

Tue 3/17

5:30 am-8:25 am

Nonstop1h 55m

$200

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 3/14

7:00 pm-8:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 3/21

9:01 pm-11:59 pm

Nonstop1h 58m

$201

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 4/16

8:00 am-9:50 am

1 stop26h 50m

Chicago O'Hare Intl

Sun 4/19

10:50 am-1:00 pm

1 stop25h 10m

$202

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 4/14

4:59 pm-9:36 pm

1 stop5h 37m

Chicago O'Hare Intl

Wed 4/15

9:41 am-4:42 pm

1 stop6h 01m

$207

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 cheapest month to fly to Chicago?

The month of May is, on average, the cheapest month to fly to Chicago from Washington, D.C. Reagan-National Airport, with most prices found around $277. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during September average around $279.

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 $381. 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 $506.

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 $365. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $421.

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 $320 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 $256 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?

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

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

As of February 2026, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 3% 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	$166
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 $166. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $303.

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 February 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 (15.46% of total bookings). The next most popular plane models are Boeing 737-800 (12.39%), Boeing 737 MAX 8 (12.16%), and Boeing 737-900 (6.43%).
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 (36% of total bookings). The next most popular airlines are American Airlines (33%), United Airlines (30%), 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 3,044 reviews	Search Frontier flights
American Airlines	PriceFrom $161	Free Cancellation	Rating 7.2 11,339 reviews	Search American Airlines flights
Southwest	PriceFrom $179	Free Cancellation	Rating 8.0 4,300 reviews	Search Southwest flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 9,342 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 26 times per week, with 4,300 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 $179 (round-trip), much lower than the average airfare cost of $315 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. Reagan-National Airport to Chicago
United Airlines (7.4/10 from 9,342 reviews) operates around 70 flights from Washington, D.C. Reagan-National Airport to Chicago in any given week. The average United Airlines airfare for this route is around $332, with deals from around $202 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

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

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

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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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How to get the cheapest flight ticket from Washington, D.C. Reagan-National Airport to 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

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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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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?

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

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