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Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $82

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. Reagan-National Airport to Chicago departing on 10/15. 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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Find the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago

Cheap round-trip flights

Southwest Logo
6:00 am - 12:45 pmDCA-ORD
7h 45m1 stop
Southwest Logo
12:40 pm - 8:30 pmORD-DCA
6h 50m1 stop
$137Southwest
Find Deal
週三, 10月 1 - 週六, 10月 4
Southwest Logo
3:20 pm - 4:30 pmDCA-MDW
2h 10mnonstop
Southwest Logo
1:25 pm - 10:00 pmMDW-DCA
7h 35m2 stops
$141Southwest
Find Deal
週三, 12月 17 - 週二, 1月 13
United Airlines Logo
7:00 am - 10:53 amDCA-ORD
4h 53m1 stop
United Airlines Logo
7:40 pm - 10:43 pmORD-DCA
2h 03mnonstop
$143United Airlines
Find Deal
週六, 10月 4 - 週六, 10月 4
United Airlines Logo
12:00 pm - 1:14 pmDCA-ORD
2h 14mnonstop
United Airlines Logo
6:00 am - 8:58 amORD-DCA
1h 58mnonstop
$149United Airlines
Find Deal
週五, 10月 3 - 週日, 10月 5
American Airlines Logo
10:45 pm - 11:50 pmDCA-ORD
2h 05mnonstop
American Airlines Logo
6:07 am - 9:00 amORD-DCA
1h 53mnonstop
$150American Airlines
Find Deal
週五, 10月 24 - 週日, 10月 26
American Airlines Logo
10:45 pm - 11:50 pmDCA-ORD
2h 05mnonstop
American Airlines Logo
7:15 pm - 10:15 pmORD-DCA
2h 00mnonstop
$159American Airlines
Find Deal
週五, 10月 10 - 週二, 10月 21
Frontier Logo
6:31 pm - 11:53 pmDCA-ORD
30h 22m1 stop
Frontier Logo
10:51 am - 9:59 pmORD-DCA
10h 08m1 stop
$173Frontier
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週五, 10月 24 - 週一, 10月 27
Frontier Logo
6:00 pm - 9:37 amDCA-ORD
16h 37m1 stop
Frontier Logo
5:35 am - 12:10 pmORD-DCA
29h 35m1 stop
$174Frontier
Find Deal
週六, 9月 27 - 週日, 10月 5
Delta Logo
6:00 am - 9:10 amDCA-ORD
4h 10m1 stop
Delta Logo
5:00 pm - 10:57 pmORD-DCA
4h 57m1 stop
$197Delta
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週六, 10月 4 - 週六, 10月 4
Delta Logo
9:45 am - 12:28 pmDCA-MDW
3h 43m1 stop
Delta Logo
10:40 am - 5:17 pmMDW-DCA
5h 37m1 stop
$197Delta
Find Deal
週二, 10月 28 - 週二, 11月 4

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

Our best Southwest deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets
Southwest
Oct 1
DCA6:00 amWashington, D.C. Reagan-National
7h 45m
1 stop
ORD12:45 pmChicago O'Hare Intl
Oct 4
ORD12:40 pmChicago O'Hare Intl
6h 50m
1 stop
DCA8:30 pmWashington, D.C. Reagan-National
$137
Find similar
Southwest
Dec 17
DCA3:20 pmWashington, D.C. Reagan-National
2h 10m
MDW4:30 pmChicago Midway
Jan 13
MDW1:25 pmChicago Midway
7h 35m
2 stops
DCA10:00 pmWashington, D.C. Reagan-National
$141
Find similar
Southwest
Oct 1
DCA11:35 amWashington, D.C. Reagan-National
10h 55m
2 stops
ORD9:30 pmChicago O'Hare Intl
Oct 4
ORD12:40 pmChicago O'Hare Intl
6h 50m
1 stop
DCA8:30 pmWashington, D.C. Reagan-National
$142
Find similar

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
Oct 4
DCA7:00 amWashington, D.C. Reagan-National
4h 53m
1 stop
ORD10:53 amChicago O'Hare Intl
Oct 4
ORD7:40 pmChicago O'Hare Intl
2h 03m
DCA10:43 pmWashington, D.C. Reagan-National
$143
Find similar
United Airlines
Oct 3
DCA12:00 pmWashington, D.C. Reagan-National
2h 14m
ORD1:14 pmChicago O'Hare Intl
Oct 5
ORD6:00 amChicago O'Hare Intl
1h 58m
DCA8:58 amWashington, D.C. Reagan-National
$149
Find similar
United Airlines
Oct 22
DCA6:00 amWashington, D.C. Reagan-National
5h 38m
1 stop
ORD10:38 amChicago O'Hare Intl
Oct 25
ORD7:40 pmChicago O'Hare Intl
2h 03m
DCA10:43 pmWashington, D.C. Reagan-National
$152
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. Reagan-National Airport to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated 9月 15, 2025.
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

週三 10/1

6:00 am-12:45 pm

1 stop7h 45m

Chicago O'Hare Intl

週六 10/4

12:40 pm-8:30 pm

1 stop6h 50m

$137

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

週三 12/17

3:20 pm-4:30 pm

Nonstop2h 10m

Chicago Midway

週二 1/13

1:25 pm-10:00 pm

2 stops7h 35m

$141

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

週六 10/4

7:00 am-10:53 am

1 stop4h 53m

Chicago O'Hare Intl

週六 10/4

7:40 pm-10:43 pm

Nonstop2h 03m

$143

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

週五 10/3

12:00 pm-1:14 pm

Nonstop2h 14m

Chicago O'Hare Intl

週日 10/5

6:00 am-8:58 am

Nonstop1h 58m

$149

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

週五 10/24

10:45 pm-11:50 pm

Nonstop2h 05m

Chicago O'Hare Intl

週日 10/26

6:07 am-9:00 am

Nonstop1h 53m

$150

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

週五 10/10

10:45 pm-11:50 pm

Nonstop2h 05m

Chicago O'Hare Intl

週二 10/21

7:15 pm-10:15 pm

Nonstop2h 00m

$159

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

週五 10/24

6:31 pm-11:53 pm

1 stop30h 22m

Chicago O'Hare Intl

週一 10/27

10:51 am-9:59 pm

1 stop10h 08m

$173

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

週六 9/27

6:00 pm-9:37 am

1 stop16h 37m

Chicago O'Hare Intl

週日 10/5

5:35 am-12:10 pm

1 stop29h 35m

$174

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

週六 10/4

6:00 am-9:10 am

1 stop4h 10m

Chicago O'Hare Intl

週六 10/4

5:00 pm-10:57 pm

1 stop4h 57m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

週二 10/28

9:45 am-12:28 pm

1 stop3h 43m

Chicago Midway

週二 11/4

10:40 am-5:17 pm

1 stop5h 37m

$197

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

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

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Washington, D.C. Reagan-National Airport, with most prices found around $270. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during May average around $273.

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 $386. 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 $498.

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 $336. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $434.

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 $308 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 $243 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.

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

As of September 2025, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 16% 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

$149

Fastest flight time

1h 55m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Washington, D.C. Reagan-National Airport in the past 72 hours is $149. 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 2 airports near Chicago: 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 2h 00m 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?

  • 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?

  • What is the most popular airline 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
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $99Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
American AirlinesPriceFrom $163Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $178Free CancellationRating
8.0
4,245 reviews
Search Southwest flights
United AirlinesPriceFrom $200Free CancellationRating
7.4
8,931 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 31 times per week, with 4,245 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 $178 (round-trip), much lower than the average airfare cost of $304 for Southwest flights on this route.

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

    United Airlines (7.4/10 from 8,931 reviews) operates around 73 flights from Washington, D.C. Reagan-National Airport to Chicago in any given week. The average United Airlines airfare for this route is around $333, with deals from around $200 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport