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 46% 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.

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

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 May 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.

$99 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 $439 to $307. The lowest price recently found on this route was $233.

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

As of May 2026, there are 51 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 at noon.

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

As of May 2026, 360 flights take off from Washington, D.C. Reagan-National Airport and land in Chicago each week. The most common flight departure day for this route is Fri, with 18% of weekly flights taking off on this day.

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

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

2:45 pm - 5:50 pm

DCA

MDW

4h 05m

1 stop

8:00 am - 3:15 pm

MDW

DCA

6h 15m

1 stop

$233Southwest

lun, giu 1 - mer, giu 3

1:59 pm - 8:32 pm

DCA

ORD

7h 33m

1 stop

9:37 pm - 9:58 pm

ORD

DCA

23h 21m

1 stop

$235Frontier

ven, mag 29 - lun, giu 1

5:00 pm - 9:56 pm

DCA

ORD

5h 56m

1 stop

6:00 am - 12:46 pm

ORD

DCA

5h 46m

1 stop

$238Delta

sab, giu 6 - mer, giu 10

6:05 am - 8:43 am

DCA

MDW

3h 38m

1 stop

11:05 am - 5:25 pm

MDW

DCA

5h 20m

1 stop

$238Delta

sab, giu 6 - mer, giu 10

7:46 am - 9:00 am

DCA

ORD

2h 14mnonstop

7:00 am - 9:59 am

ORD

DCA

1h 59mnonstop

$239United Airlines

gio, ago 13 - sab, ago 15

6:40 pm - 7:35 pm

DCA

MDW

1h 55mnonstop

5:45 am - 8:30 am

MDW

DCA

1h 45mnonstop

$239Southwest

sab, set 19 - lun, set 21

1:59 pm - 8:32 pm

DCA

ORD

7h 33m

1 stop

9:37 pm - 12:59 pm

ORD

DCA

14h 22m

1 stop

$240Frontier

sab, mag 30 - mar, giu 2

10:10 pm - 11:30 pm

DCA

ORD

2h 20mnonstop

5:55 pm - 8:59 pm

ORD

DCA

2h 04mnonstop

$243American Airlines

ven, lug 3 - mer, lug 8

1:00 pm - 2:18 pm

DCA

ORD

2h 18mnonstop

7:00 am - 9:59 am

ORD

DCA

1h 59mnonstop

$247United Airlines

lun, giu 22 - mer, giu 24

10:13 am - 11:32 am

DCA

ORD

2h 19mnonstop

6:00 am - 9:14 am

ORD

DCA

2h 14mnonstop

$248American Airlines

mer, mag 27 - mer, giu 17

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

Jul 3

DCA1:59 pmWashington, D.C. Reagan-National

2h 24m

ORD3:23 pmChicago O'Hare Intl

Jul 8

ORD9:42 amChicago O'Hare Intl

2h 02m

DCA12:44 pmWashington, D.C. Reagan-National

$243

American Airlines

May 27

DCA10:13 amWashington, D.C. Reagan-National

2h 19m

ORD11:32 amChicago O'Hare Intl

Jun 17

ORD6:00 amChicago O'Hare Intl

2h 14m

DCA9:14 amWashington, D.C. Reagan-National

$248

American Airlines

Aug 13

DCA5:13 pmWashington, D.C. Reagan-National

5h 47m

1 stop

ORD10:00 pmChicago O'Hare Intl

Aug 17

ORD6:59 amChicago O'Hare Intl

2h 01m

DCA10:00 amWashington, D.C. Reagan-National

$249

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 29

DCA1:59 pmWashington, D.C. Reagan-National

7h 33m

1 stop

ORD8:32 pmChicago O'Hare Intl

Jun 1

ORD9:37 pmChicago O'Hare Intl

23h 21m

1 stop

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

$235

Frontier

May 29

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

14h 32m

1 stop

ORD8:32 pmChicago O'Hare Intl

Jun 2

ORD9:37 pmChicago O'Hare Intl

14h 22m

1 stop

DCA12:59 pmWashington, D.C. Reagan-National

$240

Frontier

May 30

DCA1:59 pmWashington, D.C. Reagan-National

7h 33m

1 stop

ORD8:32 pmChicago O'Hare Intl

Jun 1

ORD9:37 pmChicago O'Hare Intl

18h 22m

1 stop

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

$242

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 - MDW

DCAMDW

Washington, D.C. Reagan-National

lun 6/1

2:45 pm-5:50 pm

1 stop4h 05m

Chicago Midway

mer 6/3

8:00 am-3:15 pm

1 stop6h 15m

$233

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

ven 5/29

1:59 pm-8:32 pm

1 stop7h 33m

Chicago O'Hare Intl

lun 6/1

9:37 pm-9:58 pm

1 stop23h 21m

$235

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

sab 6/6

5:00 pm-9:56 pm

1 stop5h 56m

Chicago O'Hare Intl

mer 6/10

6:00 am-12:46 pm

1 stop5h 46m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

sab 6/6

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

mer 6/10

11:05 am-5:25 pm

1 stop5h 20m

$238

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

gio 8/13

7:46 am-9:00 am

Nonstop2h 14m

Chicago O'Hare Intl

sab 8/15

7:00 am-9:59 am

Nonstop1h 59m

$239

Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

sab 9/19

6:40 pm-7:35 pm

Nonstop1h 55m

Chicago Midway

lun 9/21

5:45 am-8:30 am

Nonstop1h 45m

$239

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

sab 5/30

1:59 pm-8:32 pm

1 stop7h 33m

Chicago O'Hare Intl

mar 6/2

9:37 pm-12:59 pm

1 stop14h 22m

$240

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

ven 7/3

10:10 pm-11:30 pm

Nonstop2h 20m

Chicago O'Hare Intl

mer 7/8

5:55 pm-8:59 pm

Nonstop2h 04m

$243

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

lun 6/22

1:00 pm-2:18 pm

Nonstop2h 18m

Chicago O'Hare Intl

mer 6/24

7:00 am-9:59 am

Nonstop1h 59m

$247

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

mer 5/27

10:13 am-11:32 am

Nonstop2h 19m

Chicago O'Hare Intl

mer 6/17

6:00 am-9:14 am

Nonstop2h 14m

$248

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

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 January is, on average, the cheapest month to fly to Chicago from Washington, D.C. Reagan-National Airport, with most prices found around $29. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during October average around $84.

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 $393. 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. Reagan-National Airport to Chicago for around $514.

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 $385. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $426.

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

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

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport 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 $340 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 $276 on momondo.

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 May 2026, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 10% 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	$195
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 $195. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $321.

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

Frequently asked questions about flying from Washington, D.C. Reagan-National Airport to Chicago

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 May 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 Boeing 737 MAX 8 (14.64% of total bookings). The next most popular plane models are Airbus A319 (14.27%), Boeing 737-800 (14.22%), and Airbus A320-100/200 (8.79%).
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 United Airlines (36% of total bookings). The next most popular airlines are Southwest (33%), American 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 $58	Free Cancellation	Rating 5.6 2,951 reviews	Search Frontier flights
American Airlines	PriceFrom $169	Free Cancellation	Rating 7.1 11,665 reviews	Search American Airlines flights
Southwest	PriceFrom $191	Free Cancellation	Rating 8.0 4,299 reviews	Search Southwest flights
United Airlines	PriceFrom $210	Free Cancellation	Rating 7.4 9,722 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 33 times per week, with 4,299 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 $191 (round-trip), much lower than the average airfare cost of $334 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. Reagan-National Airport to Chicago
United Airlines (7.4/10 from 9,722 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 $363, with deals from around $210 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

Munster

Schererville

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 $99

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

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

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?

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

Frequently asked questions about flying from Washington, D.C. Reagan-National Airport to 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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