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

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

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 50% 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.

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.

$89 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 August 2026, there are 29 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 45% of flights taking off at noon.

Discover deals from 900+ travel sites with momondo.

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 - 12:23 am-

7h 23m

6:30 am - 12:11 pm-

28h 41m

$190Frontier

Tue, Sep 15 - Wed, Sep 16

1:00 pm - 12:23 am-

12h 23m

6:30 am - 12:11 pm-

28h 41m

$195Frontier

Wed, Sep 16 - Wed, Sep 23

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. Reagan-National Airport to Chicago

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

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

Sep 10

DCA1:06 pmWashington, D.C. Reagan-National

12h 17m

1 stop

ORD12:23 amChicago O'Hare Intl

Sep 14

ORD6:30 amChicago O'Hare Intl

14h 29m

1 stop

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

$195

Frontier

Aug 25

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

20h 36m

1 stop

ORD1:36 pmChicago O'Hare Intl

Aug 29

ORD2:41 pmChicago O'Hare Intl

21h 10m

1 stop

DCA12:51 pmWashington, D.C. Reagan-National

$196

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

Our best JetBlue deals on Washington, D.C. Reagan-National Airport 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

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

Tue 9/15

6:00 pm-12:23 am

1 stop7h 23m

Chicago O'Hare Intl

Wed 9/16

6:30 am-12:11 pm

1 stop28h 41m

$190

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/16

1:00 pm-12:23 am

1 stop12h 23m

Chicago O'Hare Intl

Wed 9/23

6:30 am-12:11 pm

1 stop28h 41m

$195

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. 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?

Prices are currently low for flights on this route.

Typical prices usually range from $272 to $406.
The lowest price recently found on this route was $195.

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 $312. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during February average around $318.

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. Reagan-National Airport 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. Reagan-National Airport 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. 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 $356 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 $277 on momondo.

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

There are 4 cabin classes available to choose from on Washington, D.C. Reagan-National Airport 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 August 2026, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 6% cheaper 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	$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. Reagan-National Airport in the past 72 hours is $177. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $271.

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).

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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 August 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 (15.68% of total bookings). The next most popular plane models are Boeing 737-800 (14.10%), Airbus A320-100/200 (11.93%), and Airbus A319 (10.82%).
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 (42% of total bookings). The next most popular airlines are Southwest (30%) and American Airlines (28%).

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 5.6 2,737 reviews	Search Frontier flights
American Airlines	PriceFrom $197	Free Cancellation	Rating 7.1 11,845 reviews	Search American Airlines flights
Southwest	PriceFrom $221	Free Cancellation	Rating 8.0 4,222 reviews	Search Southwest flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 10,059 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 6 times per week, with 4,221 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 $221 (round-trip), much lower than the average airfare cost of $368 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. Reagan-National Airport to Chicago
United Airlines (7.4/10 from 10,060 reviews) operates around 55 flights from Washington, D.C. Reagan-National Airport to Chicago in any given week. The average United Airlines airfare for this route is around $387, with deals from around $226 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

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

Porter

Griffith

Saint John

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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 $89

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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

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

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

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

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

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

Traveling to a place near Chicago?

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An easier way to manage your Chicago trip

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