DCA - CHI

$89 Find Cheap Flights from Reagan Washington National Airport to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Reagan-National to Chicago departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$207
Typical prices: $262-$449
Southwest
Sat 8/29Sun 9/6
DCA - MDW • 2 stops
Cheapest non-stop
$216
Typical prices: $229-$308
Southwest
Thu 9/3Mon 9/7
DCA - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Basic Economy includes a carry-on, but no seat selection or checked bag.
United Economy Plus adds legroom, while Southwest offers a free carry-on.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 13m
Direct flights
Direct flights
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+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 4% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 3h 49m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 13% price drop
Most popular
Good to know
Good to know
+1
+1
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Flight Deals

Cheap Flights from Reagan-National to Chicago (DCA-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Reagan-National to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Reagan-National to Chicago

Sat, Aug 29 - Sun, Sep 6
Southwest Logo
6:00 am - 1:20 pm
DCA
-
MDW
8h 20m
2 stops
Southwest Logo
8:55 am - 3:55 pm
MDW
-
DCA
6h 00m
1 stop
$207Southwest
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
3:30 pm - 7:20 pm
DCA
-
MDW
4h 50m
1 stop
Southwest Logo
8:40 am - 3:50 pm
MDW
-
DCA
6h 10m
2 stops
$207Southwest
Fri, Sep 11 - Mon, Sep 14
American Airlines Logo
5:00 am - 8:52 am
DCA
-
ORD
4h 52m
1 stop
American Airlines Logo
5:54 pm - 9:00 pm
ORD
-
DCA
2h 06mnonstop
$216American Airlines
Mon, Nov 23 - Tue, Dec 1
American Airlines Logo
5:00 am - 8:59 am
DCA
-
ORD
4h 59m
1 stop
American Airlines Logo
5:51 pm - 8:59 pm
ORD
-
DCA
2h 08mnonstop
$216American Airlines
Thu, Sep 10 - Thu, Sep 17
JetBlue Logo
1:15 pm - 7:01 pm
DCA
-
ORD
6h 46m
1 stop
JetBlue Logo
9:38 am - 3:59 pm
ORD
-
DCA
5h 21m
1 stop
$221JetBlue
Wed, Oct 14 - Fri, Oct 16
JetBlue Logo
6:30 am - 11:47 am
DCA
-
ORD
6h 17m
1 stop
JetBlue Logo
9:38 am - 5:24 pm
ORD
-
DCA
6h 46m
1 stop
$230JetBlue
Sat, Sep 19 - Mon, Sep 21
Frontier Logo
7:00 am - 12:23 am
DCA
-
ORD
18h 23m
1 stop
Frontier Logo
6:30 am - 9:59 pm
ORD
-
DCA
14h 29m
1 stop
$240Frontier
Thu, Sep 10 - Tue, Sep 15
Frontier Logo
1:59 pm - 9:35 pm
DCA
-
ORD
8h 36m
1 stop
Frontier Logo
10:40 pm - 12:49 pm
ORD
-
DCA
13h 09m
1 stop
$240Frontier
Sat, Nov 14 - Sat, Nov 21
United Airlines Logo
8:00 pm - 9:05 pm
DCA
-
ORD
2h 05mnonstop
United Airlines Logo
6:30 am - 9:15 am
ORD
-
DCA
1h 45mnonstop
$242United Airlines
Fri, Aug 21 - Sat, Aug 22
United Airlines Logo
10:30 am - 11:46 am
DCA
-
ORD
2h 16mnonstop
United Airlines Logo
7:45 pm - 10:52 pm
ORD
-
DCA
2h 07mnonstop
$245United Airlines
Booking Insights

KAYAK's insights & trends for Reagan-National to Chicago flights

Get data-powered insights and trends into flights from Reagan-National to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Washington, D.C. Reagan-National Airport to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Washington, D.C. Reagan-National Airport to Chicago departing in September.

Flight prices are below average for this route right now.

Flights to Chicago from Washington, D.C. Reagan-National Airport usually cost between $272 and $406 in September.
The lowest price found in the past 5 days was $207 on Southwest (Sep 11-Sep 12).

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Washington, D.C. Reagan-National Airport to Chicago costs $177 on the route between Washington, D.C. Reagan-National Airport (DCA) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 4% cheaper than other Washington, D.C. Reagan-National Airport-Chicago routes. The most popular route is between Washington, D.C. Reagan-National Airport (DCA) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Reagan Washington National Airport to Chicago?

The average price of all round-trip flights from Washington, D.C. Reagan-National Airport to Chicago clicked on KAYAK for each day over the last 12 months.

For Reagan Washington National Airport to Chicago, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to Reagan Washington National Airport, the best deals are generally found on Saturday, with Monday being the most expensive.

What is the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Washington, D.C. Reagan-National Airport to Chicago is September, where tickets cost $310 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $402 and $400 respectively.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $308 on average.

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Washington, D.C. Reagan-National Airport to Chicago, you should book around 4 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Expert advice

Expert advice for your flight from Reagan-National to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Ramsey Qubein

Ramsey Qubein

Expert on DCA

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Good to know

Low season

January

Cheapest flight

$89
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Reagan Washington National Airport to Chicago O'Hare Airport

When to book flights from Reagan-National to Chicago

Are your dates flexible? Find out the best times to travel from Reagan-National to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Reagan Washington National Airport to Chicago flights

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

    In the last 5 days, the lowest price for a flight from Washington, D.C. Reagan-National Airport to Chicago was $89 for a one-way ticket and $207 for a round-trip.

  • Do I need a passport to fly between Reagan Washington National Airport and Chicago?

    A passport is not required to fly from Reagan Washington National Airport to Chicago.

  • Which airports will I be using when flying from Reagan Washington National Airport to Chicago?

    Reagan Washington National Airport is served by only 1 airport and there are 2 airports in Chicago. You will leave Reagan Washington National Airport from Washington, D.C. Reagan-National and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Reagan Washington National Airport to Chicago?

    American Airlines, and Alaska Airlines offer inflight Wi-Fi service on the Reagan Washington National Airport to Chicago flight route.

  • Which aircraft models fly most regularly from Reagan Washington National Airport to Chicago?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Reagan Washington National Airport to Chicago flight route.

  • Which airline alliances offer flights from Reagan Washington National Airport to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Reagan Washington National Airport and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Reagan Washington National Airport to Chicago?

    There are nonstop flights from Reagan Washington National Airport to Chicago on a daily basis.

  • Which is the best airline for flights from Washington, D.C. to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and United Airlines. With an average price for the route of $354 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $368 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Reagan Washington National Airport to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Reagan Washington National Airport to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Reagan Washington National Airport to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Reagan Washington National Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Reagan Washington National Airport to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Reagan Washington National Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Reagan Washington National Airport to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Reagan Washington National Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Washington, D.C. Reagan-National Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $203 or less one-way and $310 or less round-trip.

Prefer to fly direct from Reagan Washington National Airport to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Washington, D.C. Reagan-National to Chicago.
Find which airlines fly direct from Washington, D.C. Reagan-National Airport to Chicago, which days they fly and book direct flights.

Direct departures

Washington, D.C. Reagan-National to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Washington, D.C. Reagan-National

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Everything you need to know for your flight from Reagan-National to Chicago

Other airlines flying from Reagan-National to Chicago

Flights from the other most popular airlines that fly from Reagan-National to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.