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Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $80

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 8/31. 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 (DCA-CHI)

Cheap round-trip flights

Frontier Logo
1:00 pm - 11:59 pmDCA-ORD
11h 59m1 stop
Frontier Logo
10:42 am - 4:59 pmORD-DCA
29h 17m1 stop
$160Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
6:00 pm - 2:51 pmDCA-MDW
21h 51m1 stop
Frontier Logo
4:48 pm - 4:59 pmMDW-DCA
23h 11m1 stop
$160Frontier
Find Deal
Thu, Sep 18 - Mon, Sep 22
JetBlue Logo
6:25 am - 12:10 pmDCA-ORD
6h 45m1 stop
JetBlue Logo
1:36 pm - 7:22 pmORD-DCA
4h 46m1 stop
$203JetBlue
Find Deal
Tue, Oct 14 - Wed, Oct 22
JetBlue Logo
6:25 am - 12:10 pmDCA-ORD
6h 45m1 stop
JetBlue Logo
1:35 pm - 7:20 pmORD-DCA
4h 45m1 stop
$206JetBlue
Find Deal
Wed, Oct 15 - Fri, Oct 24
American Airlines Logo
3:50 pm - 5:13 pmDCA-ORD
2h 23mnonstop
American Airlines Logo
8:04 pm - 11:12 pmORD-DCA
2h 08mnonstop
$217American Airlines
Find Deal
Sat, Oct 11 - Mon, Oct 13
Southwest Logo
6:35 pm - 7:30 pmDCA-MDW
1h 55mnonstop
Southwest Logo
12:15 pm - 3:10 pmMDW-DCA
1h 55mnonstop
$217Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 30
Southwest Logo
9:00 am - 10:00 amDCA-MDW
2h 00mnonstop
Southwest Logo
6:30 am - 11:20 amMDW-DCA
3h 50m1 stop
$227Southwest
Find Deal
Wed, Oct 1 - Sat, Oct 4
United Airlines Logo
7:00 am - 11:49 amDCA-ORD
5h 49m1 stop
United Airlines Logo
4:00 pm - 7:03 pmORD-DCA
2h 03mnonstop
$227United Airlines
Find Deal
Sat, Oct 4 - Tue, Oct 7
American Airlines Logo
6:59 am - 8:24 amDCA-ORD
2h 25mnonstop
American Airlines Logo
8:04 pm - 11:12 pmORD-DCA
2h 08mnonstop
$229American Airlines
Find Deal
Thu, Oct 9 - Thu, Oct 16
United Airlines Logo
6:00 am - 10:35 amDCA-ORD
5h 35m1 stop
United Airlines Logo
4:00 pm - 7:03 pmORD-DCA
2h 03mnonstop
$247United Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 3

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 5
DCA1:00 pmWashington, D.C. Reagan-National
11h 59m
1 stop
ORD11:59 pmChicago O'Hare Intl
Sep 8
ORD10:42 amChicago O'Hare Intl
29h 17m
1 stop
DCA4:59 pmWashington, D.C. Reagan-National
$160
Find similar
Frontier
Sep 18
DCA6:00 pmWashington, D.C. Reagan-National
16h 37m
1 stop
ORD9:37 amChicago O'Hare Intl
Sep 22
ORD6:00 amChicago O'Hare Intl
14h 59m
1 stop
DCA9:59 pmWashington, D.C. Reagan-National
$162
Find similar
Frontier
Oct 20
DCA1:00 pmWashington, D.C. Reagan-National
12h 59m
1 stop
ORD12:59 amChicago O'Hare Intl
Oct 24
ORD10:51 amChicago O'Hare Intl
10h 08m
1 stop
DCA9:59 pmWashington, D.C. Reagan-National
$166
Find similar

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
Oct 11
DCA3:50 pmWashington, D.C. Reagan-National
2h 23m
ORD5:13 pmChicago O'Hare Intl
Oct 13
ORD8:04 pmChicago O'Hare Intl
2h 08m
DCA11:12 pmWashington, D.C. Reagan-National
$217
Find similar
American Airlines
Sep 5
DCA4:01 pmWashington, D.C. Reagan-National
2h 22m
ORD5:23 pmChicago O'Hare Intl
Sep 15
ORD6:10 amChicago O'Hare Intl
1h 50m
DCA9:00 amWashington, D.C. Reagan-National
$227
Find similar
American Airlines
Oct 9
DCA6:59 amWashington, D.C. Reagan-National
2h 25m
ORD8:24 amChicago O'Hare Intl
Oct 16
ORD8:04 pmChicago O'Hare Intl
2h 08m
DCA11:12 pmWashington, D.C. Reagan-National
$229
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 August 26, 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

Fri 9/5

1:00 pm-11:59 pm

1 stop11h 59m

Chicago O'Hare Intl

Mon 9/8

10:42 am-4:59 pm

1 stop29h 17m

$160

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/18

6:00 pm-2:51 pm

1 stop21h 51m

Chicago Midway

Mon 9/22

4:48 pm-4:59 pm

1 stop23h 11m

$160

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 10/14

6:25 am-12:10 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 10/22

1:36 pm-7:22 pm

1 stop4h 46m

$203

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 10/15

6:25 am-12:10 pm

1 stop6h 45m

Chicago O'Hare Intl

Fri 10/24

1:35 pm-7:20 pm

1 stop4h 45m

$206

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 10/11

3:50 pm-5:13 pm

Nonstop2h 23m

Chicago O'Hare Intl

Mon 10/13

8:04 pm-11:12 pm

Nonstop2h 08m

$217

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 9/23

6:35 pm-7:30 pm

Nonstop1h 55m

Chicago Midway

Tue 9/30

12:15 pm-3:10 pm

Nonstop1h 55m

$217

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 10/1

9:00 am-10:00 am

Nonstop2h 00m

Chicago Midway

Sat 10/4

6:30 am-11:20 am

1 stop3h 50m

$227

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 10/4

7:00 am-11:49 am

1 stop5h 49m

Chicago O'Hare Intl

Tue 10/7

4:00 pm-7:03 pm

Nonstop2h 03m

$227

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 10/9

6:59 am-8:24 am

Nonstop2h 25m

Chicago O'Hare Intl

Thu 10/16

8:04 pm-11:12 pm

Nonstop2h 08m

$229

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 9/3

6:00 am-10:35 am

1 stop5h 35m

Chicago O'Hare Intl

Wed 9/3

4:00 pm-7:03 pm

Nonstop2h 03m

$247

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 September is, on average, the cheapest month to fly to Chicago from Washington, D.C. Reagan-National Airport, with most prices found around $243. 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 $267.

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 $495.

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 $333. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $439.

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 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 $309 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 $244 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 August 2025, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 2% 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

$155

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 $155. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $257.
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 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?

  • 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
3,200 reviews
Search Frontier flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $176Free CancellationRating
8.0
4,243 reviews
Search Southwest flights
United AirlinesPriceFrom $197Free CancellationRating
7.4
8,943 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 4,242 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 $176 (round-trip), much lower than the average airfare cost of $300 for Southwest flights on this route.

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

    United Airlines (7.4/10 from 8,943 reviews) operates around 59 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 $197 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