DCA - CHI

$99 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 7/25. 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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Everything you should know

Cheapest round-trip
$247
Typical prices: $178-$376
American Airlines
Sat 8/1Mon 8/3
DCA - ORD • Non-stop
Cheapest non-stop
$253
Typical prices: $239-$409
United Airlines
Wed 7/29Mon 8/3
DCA - ORD • 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
Top airlines
Cheapest • from $247 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 2h 14m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 7% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $179 (round-trip)
Shortest trip • 3h 44m (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 • 87% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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We hope you love your trip to Chicago!
Flight Deals
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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 1 - Mon, Aug 3
American Airlines Logo
8:06 pm - 9:42 pm
DCA
-
ORD
2h 36mnonstop
American Airlines Logo
5:07 am - 10:50 am
ORD
-
DCA
4h 43m
1 stop
$247American Airlines
Wed, Jul 29 - Thu, Jul 30
Southwest Logo
9:30 pm - 10:35 pm
DCA
-
MDW
2h 05mnonstop
Southwest Logo
5:00 am - 1:15 pm
MDW
-
DCA
7h 15m
1 stop
$247Southwest
Thu, Sep 3 - Tue, Sep 8
JetBlue Logo
2:25 pm - 7:55 pm
DCA
-
ORD
6h 30m
1 stop
JetBlue Logo
10:56 am - 5:56 pm
ORD
-
DCA
6h 00m
1 stop
$248JetBlue
Wed, Oct 14 - Thu, Oct 15
Delta Logo
6:00 am - 9:52 am
DCA
-
MDW
4h 52m
1 stop
Delta Logo
6:45 pm - 11:09 pm
MDW
-
DCA
3h 24m
1 stop
$248Delta
Thu, Aug 20 - Mon, Aug 24
JetBlue Logo
2:25 pm - 7:27 pm
DCA
-
ORD
6h 02m
1 stop
JetBlue Logo
11:01 am - 7:05 pm
ORD
-
DCA
7h 04m
1 stop
$249JetBlue
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
1:00 pm - 5:50 pm
DCA
-
MDW
5h 50m
2 stops
Southwest Logo
8:55 am - 11:50 am
MDW
-
DCA
1h 55mnonstop
$249Southwest
Fri, Sep 18 - Sun, Sep 20
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
$250Frontier
Fri, Aug 7 - Tue, Aug 11
American Airlines Logo
5:00 am - 9:00 am
DCA
-
ORD
5h 00m
1 stop
American Airlines Logo
5:55 pm - 8:59 pm
ORD
-
DCA
2h 04mnonstop
$253American Airlines
Tue, Aug 18 - Thu, Aug 20
Frontier Logo
7:00 am - 1:36 pm
DCA
-
ORD
7h 36m
1 stop
Frontier Logo
2:41 pm - 4:59 pm
ORD
-
DCA
25h 18m
1 stop
$254Frontier
Mon, Aug 3 - Tue, Aug 4
Delta Logo
6:00 am - 11:51 am
DCA
-
MDW
6h 51m
1 stop
Delta Logo
6:42 pm - 10:59 pm
MDW
-
DCA
3h 17m
1 stop
$257Delta
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 August.

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 $211 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, 7% 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 Monday 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 January, where tickets cost $29 (return) on average. On the other hand, the most expensive months are June and May, where the average cost of round-trip tickets is $790 and $783 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 $310 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 seasonJanuary
Cheapest flight$99
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 2% 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 $99 for a one-way ticket and $247 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 $347 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $360 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 $183 or less one-way and $322 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 3 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.
7.9
SouthwestOverall score based on 4246 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

No delays and arrived to destination 30 min early. Staff was super friendly.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

Awesome experience. No in-flight video or meal. Still do not like the boarding process.

On time, good crew, easy flight. Just like the old days!

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

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.

Never nice, United Express partners always do an amazing job.

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

Almost 2 hour delay in boarding with all standing ready to board at original time. No explanation given.

I was forced to gate check my carry on luggage. Somehow it did not arrive at my destination. I still have yet to receive my bag r days after arrival.

Boarding area is a mess. Lines not bounded and gate area too small. Food options (on this specific flight) were poor and you couldn’t pick part of it since it was like a mash of chicken and other unrecognisable stuff. Comfort of seats along with child noise made it difficult to get a good sleep. Last, the flight attendant that served my aisle was rude (others seemed fine) towards me and others.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

Overall a good experience, however Wifi was not working on the flight.

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Delays with no explanation. It could have been handled better.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Perfect flight. On time departure and early arrival. 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.