DCA - CHI

$78 Find Cheap Flights from Reagan Washington National Airport to Chicago

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 1/17. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
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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

Fri, Nov 14 - Mon, Nov 17
Frontier Logo
2:00 pm - 12:15 amDCA-ORD
11h 15m1 stop
Frontier Logo
6:00 am - 9:59 pmORD-DCA
14h 59m1 stop
$143Frontier
Find Deal
Wed, Nov 12 - Fri, Nov 14
Frontier Logo
8:15 am - 11:30 amDCA-MDW
28h 15m1 stop
Frontier Logo
12:30 pm - 9:59 pmMDW-DCA
8h 29m1 stop
$143Frontier
Find Deal
Wed, Nov 12 - Mon, Nov 17
JetBlue Logo
4:55 pm - 8:52 pmDCA-ORD
4h 57m1 stop
JetBlue Logo
6:45 am - 2:36 pmORD-DCA
6h 51m1 stop
$153JetBlue
Find Deal
Sat, Jan 10 - Thu, Jan 15
JetBlue Logo
6:15 am - 1:10 pmDCA-ORD
7h 55m1 stop
JetBlue Logo
2:05 pm - 10:47 pmORD-DCA
7h 42m1 stop
$154JetBlue
Find Deal
Mon, Nov 24 - Thu, Nov 27
American Airlines Logo
11:55 am - 1:11 pmDCA-ORD
2h 16mnonstop
American Airlines Logo
11:37 am - 2:24 pmORD-DCA
1h 47mnonstop
$219American Airlines
Find Deal
Sun, Feb 15 - Sun, Feb 15
American Airlines Logo
9:20 am - 10:41 amDCA-ORD
2h 21mnonstop
American Airlines Logo
4:00 pm - 6:59 pmORD-DCA
1h 59mnonstop
$220American Airlines
Find Deal
Wed, Dec 3 - Thu, Dec 4
Southwest Logo
6:00 am - 7:05 amDCA-MDW
2h 05mnonstop
Southwest Logo
3:30 pm - 6:15 pmMDW-DCA
1h 45mnonstop
$237Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 3
United Airlines Logo
7:30 am - 8:57 amDCA-ORD
2h 27mnonstop
United Airlines Logo
4:00 pm - 7:07 pmORD-DCA
2h 07mnonstop
$237United Airlines
Find Deal
Wed, Dec 17 - Sat, Jan 17
Southwest Logo
9:30 am - 10:35 amDCA-MDW
2h 05mnonstop
Southwest Logo
3:30 pm - 6:15 pmMDW-DCA
1h 45mnonstop
$238Southwest
Find Deal
Thu, Nov 27 - Wed, Dec 3
United Airlines Logo
7:30 am - 8:56 amDCA-ORD
2h 26mnonstop
United Airlines Logo
7:35 pm - 10:42 pmORD-DCA
2h 07mnonstop
$238United Airlines
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Southwest offers two free checked bags, saving fees.
DCA is conveniently accessible via the metro line.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $143 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
DCA-MDW
Cheapest • 11% average savings
DCA-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 53% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 10% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$143
Overall average: $331
Frontier
Fri 11/14Mon 11/17
DCA - ORD • 1 stop
Cheapest non-stop
$219
Typical prices: $289-$511
American Airlines
Mon 11/24Thu 11/27
DCA - ORD • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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.

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 $205 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, 11% 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, Friday 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 Thursday, 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 February, where tickets cost $267 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $355 and $331 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 $293 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 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Expert advice

Expert advice for your flight from Reagan-National to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Southwest

Southwest's Rapid Rewards program offers unlimited rewards seats and no blackout dates.


Southwest's free carry-on policy includes one carry-on and a personal item per passenger.

Read more about Southwestby Blane Bachelor
American Airlines

American's Main Cabin Extra offers early boarding and complimentary alcoholic drinks.


American's Basic Economy includes carry-on but no free checked bags or seat selection.

United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy seats.


United's Priority Boarding puts you in Zone 2, avoiding gate-checking carry-ons.

Airports
DCA

DCA is conveniently accessible via the metro line, reaching the terminal in under 30 minutes from downtown D.C.

Read more about DCAby Ramsey Qubein
ORD

Take the CTA Blue Line from ORD to downtown Chicago in about 45 minutes, avoiding traffic delays.

Read more about ORDby Stefanie Waldek
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and ORD

Stefanie Waldek

Stefanie Waldek

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.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on DCA

Ramsey Qubein

Ramsey Qubein

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.

Read more

Good to know

Low seasonFebruary
Cheapest flight$78
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 9% lower on average.
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 3 days, the lowest price for a flight from Washington, D.C. Reagan-National Airport to Chicago was $78 for a one-way ticket and $143 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, Alaska Airlines, and Delta 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 737-800 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Reagan Washington National Airport and Chicago, with Star Alliance 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 $289 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 $326 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 $175 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

Reviews of the top 4 airlines serving from Reagan-National to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Reagan-National to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

We fly American Airlines quite a bit. And we always fly business class when traveling internationally. We were a bit disappointed with the comfort of this particular plane as well as the entertainment options.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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.

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