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Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $70

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 1/28. 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

Enter your travel dates to find the best prices.
Frontier Logo
2:00 pm - 9:24 pm
DCA
-
ORD
8h 24m1 stop
Frontier Logo
7:41 pm - 4:59 pm
ORD
-
DCA
20h 18m1 stop
$163Frontier
Thu, Jan 15 - Thu, Jan 22
JetBlue Logo
12:20 pm - 5:43 pm
DCA
-
ORD
6h 23m1 stop
JetBlue Logo
7:45 am - 2:29 pm
ORD
-
DCA
5h 44m1 stop
$164JetBlue
Sat, Jan 24 - Sat, Jan 31
Frontier Logo
8:00 am - 10:57 am
DCA
-
ORD
27h 57m1 stop
Frontier Logo
12:07 pm - 1:02 pm
ORD
-
DCA
23h 55m1 stop
$180Frontier
Sat, Jan 24 - Sun, Jan 25
Frontier Logo
2:00 pm - 6:31 pm
DCA
-
ORD
29h 31m1 stop
Frontier Logo
12:07 pm - 1:02 pm
ORD
-
DCA
23h 55m1 stop
$181Frontier
Wed, Jan 21 - Fri, Jan 23
Frontier Logo
8:00 am - 6:31 pm
DCA
-
ORD
11h 31m1 stop
Frontier Logo
7:41 pm - 1:02 pm
ORD
-
DCA
16h 21m1 stop
$183Frontier
Thu, Jan 22 - Thu, Jan 29
Multiple Airlines Logo
8:00 am - 6:31 pm
DCA
-
ORD
11h 31m1 stop
Multiple Airlines Logo
7:45 am - 4:19 pm
ORD
-
DCA
7h 34m1 stop
$185Multiple Airlines
Thu, Jan 22 - Sun, Jan 25
Frontier Logo
2:00 pm - 6:31 pm
DCA
-
ORD
29h 31m1 stop
Frontier Logo
12:07 pm - 9:59 pm
ORD
-
DCA
8h 52m1 stop
$188Frontier
Wed, Jan 28 - Fri, Jan 30
Southwest Logo
8:25 am - 9:45 am
DCA
-
MDW
2h 20mnonstop
Southwest Logo
10:15 am - 1:00 pm
MDW
-
DCA
1h 45mnonstop
$223Southwest
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
4:40 pm - 5:50 pm
DCA
-
MDW
2h 10mnonstop
Southwest Logo
7:05 am - 10:00 am
MDW
-
DCA
1h 55mnonstop
$227Southwest
Sat, Jan 17 - Wed, Jan 21
Delta Logo
6:00 am - 10:27 am
DCA
-
MDW
5h 27m1 stop
Delta Logo
6:14 pm - 10:57 pm
MDW
-
DCA
3h 43m1 stop
$243Delta
Sun, Jan 18 - Sun, Jan 18

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
Dec 31
DCA6:00 amWashington, D.C. Reagan-National
2h 30m
ORD7:30 amChicago O'Hare Intl
Jan 1
ORD8:00 amChicago O'Hare Intl
1h 56m
DCA10:56 amWashington, D.C. Reagan-National
$223
Find similar
American Airlines
Feb 7
DCA6:00 amWashington, D.C. Reagan-National
2h 22m
ORD7:22 amChicago O'Hare Intl
Feb 14
ORD7:57 pmChicago O'Hare Intl
2h 02m
DCA10:59 pmWashington, D.C. Reagan-National
$229
Find similar
American Airlines
Jan 28
DCA7:57 amWashington, D.C. Reagan-National
3h 54m
1 stop
ORD10:51 amChicago O'Hare Intl
Feb 11
ORD6:00 amChicago O'Hare Intl
1h 56m
DCA8:56 amWashington, D.C. Reagan-National
$241
Find similar

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
Jan 15
DCA2:00 pmWashington, D.C. Reagan-National
8h 24m
1 stop
ORD9:24 pmChicago O'Hare Intl
Jan 22
ORD7:41 pmChicago O'Hare Intl
20h 18m
1 stop
DCA4:59 pmWashington, D.C. Reagan-National
$163
Find similar
Frontier
Jan 24
DCA8:00 amWashington, D.C. Reagan-National
27h 57m
1 stop
ORD10:57 amChicago O'Hare Intl
Jan 25
ORD12:07 pmChicago O'Hare Intl
23h 55m
1 stop
DCA1:02 pmWashington, D.C. Reagan-National
$180
Find similar
Frontier
Jan 21
DCA2:00 pmWashington, D.C. Reagan-National
29h 31m
1 stop
ORD6:31 pmChicago O'Hare Intl
Jan 23
ORD12:07 pmChicago O'Hare Intl
23h 55m
1 stop
DCA1:02 pmWashington, D.C. Reagan-National
$181
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 December 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

Thu 1/15

2:00 pm-9:24 pm

1 stop8h 24m

Chicago O'Hare Intl

Thu 1/22

7:41 pm-4:59 pm

1 stop20h 18m

$163

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 1/24

12:20 pm-5:43 pm

1 stop6h 23m

Chicago O'Hare Intl

Sat 1/31

7:45 am-2:29 pm

1 stop5h 44m

$164

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 1/24

8:00 am-10:57 am

1 stop27h 57m

Chicago O'Hare Intl

Sun 1/25

12:07 pm-1:02 pm

1 stop23h 55m

$180

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 1/21

2:00 pm-6:31 pm

1 stop29h 31m

Chicago O'Hare Intl

Fri 1/23

12:07 pm-1:02 pm

1 stop23h 55m

$181

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 1/22

8:00 am-6:31 pm

1 stop11h 31m

Chicago O'Hare Intl

Thu 1/29

7:41 pm-1:02 pm

1 stop16h 21m

$183

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 1/22

8:00 am-6:31 pm

1 stop11h 31m

Chicago O'Hare Intl

Sun 1/25

7:45 am-4:19 pm

1 stop7h 34m

$185

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 1/28

2:00 pm-6:31 pm

1 stop29h 31m

Chicago O'Hare Intl

Fri 1/30

12:07 pm-9:59 pm

1 stop8h 52m

$188

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 1/17

8:25 am-9:45 am

Nonstop2h 20m

Chicago Midway

Sun 1/18

10:15 am-1:00 pm

Nonstop1h 45m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 1/17

4:40 pm-5:50 pm

Nonstop2h 10m

Chicago Midway

Wed 1/21

7:05 am-10:00 am

Nonstop1h 55m

$227

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 1/18

6:00 am-10:27 am

1 stop5h 27m

Chicago Midway

Sun 1/18

6:14 pm-10:57 pm

1 stop3h 43m

$243

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 $267. 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 $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 $502.

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 $342. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $424.

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 $312 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 $247 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 December 2025, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 0% 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

$173

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 $173. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $319.
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?

  • 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 $81Free CancellationRating
5.8
3,070 reviews
Search Frontier flights
American AirlinesPriceFrom $167Free CancellationRating
7.2
11,064 reviews
Search American Airlines flights
SouthwestPriceFrom $178Free CancellationRating
8.0
4,258 reviews
Search Southwest flights
United AirlinesPriceFrom $198Free CancellationRating
7.4
9,115 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 36 times per week, with 4,258 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 $306 for Southwest flights on this route.

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

    United Airlines (7.4/10 from 9,115 reviews) operates around 40 flights from Washington, D.C. Reagan-National Airport to Chicago in any given week. The average United Airlines airfare for this route is around $325, with deals from around $198 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
Portage
Lansing
Valparaiso
Schererville
Munster
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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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