DCA - CHI

$75 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 3/26. 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.
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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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Cheap Flight Deals 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.

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Reagan-National to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
1:03 pm - 12:15 amDCA-ORD
12h 12m1 stop
6:45 am - 9:59 pmORD-DCA
14h 14m1 stop
$149Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 8
6:00 pm - 12:21 amDCA-MDW
7h 21m1 stop
6:45 am - 9:59 pmMDW-DCA
14h 14m1 stop
$149Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 8
2:54 pm - 4:15 pmDCA-ORD
2h 21mnonstop
11:29 am - 2:20 pmORD-DCA
1h 51mnonstop
$176American Airlines
Find Deal
Tue, Apr 1 - Mon, Apr 7
9:21 am - 10:38 amDCA-ORD
2h 17mnonstop
7:21 pm - 10:15 pmORD-DCA
1h 54mnonstop
$177American Airlines
Find Deal
Thu, Mar 20 - Thu, Mar 27
11:55 am - 1:00 pmDCA-MDW
2h 05mnonstop
9:40 am - 12:30 pmMDW-DCA
1h 50mnonstop
$177Southwest
Find Deal
Tue, Apr 1 - Tue, Apr 8
8:55 pm - 9:55 pmDCA-MDW
2h 00mnonstop
5:25 pm - 8:20 pmMDW-DCA
1h 55mnonstop
$178Southwest
Find Deal
Wed, May 21 - Sun, May 25
1:00 pm - 2:15 pmDCA-ORD
2h 15mnonstop
12:55 pm - 7:42 pmORD-DCA
5h 47m1 stop
$187United Airlines
Find Deal
Tue, Apr 1 - Tue, Apr 8
5:00 pm - 6:14 pmDCA-ORD
2h 14mnonstop
11:15 am - 2:11 pmORD-DCA
1h 56mnonstop
$191United Airlines
Find Deal
Mon, Mar 31 - Wed, Apr 2
5:55 pm - 10:43 pmDCA-ORD
5h 48m1 stop
2:55 pm - 8:34 pmORD-DCA
4h 39m1 stop
$194Delta
Find Deal
Tue, Apr 1 - Thu, Apr 3
8:00 am - 12:20 pmDCA-ORD
5h 20m1 stop
12:20 pm - 6:42 pmORD-DCA
5h 22m1 stop
$217Delta
Find Deal
Sat, Apr 19 - Tue, Apr 22

Expert advice for your flight from Reagan-National to Chicago

Our travel pros reveal their best tips for your Reagan-National to Chicago journey.
Airlines
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.

Southwest

Southwest offers two free checked bags, saving on baggage fees.


Southwest's EarlyBird Check-In improves boarding position, avoiding middle seats.

Read more about Southwestby Blane Bachelor
Airports
DCA

DCA's metro access makes it easy to reach from downtown D.C. in under 30 minutes, ideal for business travelers.

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
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
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
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

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.

Flights from Reagan-National to Chicago - Travel Insights & Trends

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Washington, D.C. Reagan-National Airport to Chicago.
Our data shows that the cheapest route for a return flight from Washington, D.C. Reagan-National Airport to Chicago cost $178 and was between Washington, D.C. Reagan-National Airport (DCA) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $178.

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, Wednesday 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 Sunday 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 $263 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $353 and $348 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 $295 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. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

$75
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 8% 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 $75 for a one-way ticket and $149 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 737-800 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?

    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 Delta?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and Delta. With an average price for the route of $273 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $318 and an overall rating of 8.0.

  • 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.

See more FAQs

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 $142 or less one-way and $238 or less round-trip.

Prefer to fly direct from Reagan Washington National Airport 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

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Friday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

See more direct flights

Direct returns

Chicago to Washington, D.C. Reagan-National

Monday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Friday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +9 more

ANA, Air New Zealand, +10 more

See more direct flights
See more direct flights

Top 5 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.
8.1
SouthwestOverall score based on 4333 reviews
8.2Boarding
7.6Entertainment
7.1Food
8.1Comfort
8.7Crew
Airline reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

8.0 ExcellentJames, Feb 2025SRQ - DEN
Read more Southwest reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

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

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

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

Standard. No different than a discount carrier on a short trip.

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

I blame kayak for my last trip to dca. Kayak cancelled my direct flight and put on a one stop flight and made lost whole day from my vacation and had not even refunded my ticket.

Per usual, flight status, staff courtesy and professionalism were excellent

I flew out of Reagan National. My flight was delayed, delayed, delayed, and then canceled ...THREE TIMES over TWO DAYS. Staff were seemingly not empowered to provide information on why the flights were screwed up. A real nightmare.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

I had two wonderful flights - very relaxing and got me there early!

Cancelled and rebooked twice in one day with a drop in seat class. Not good at all.

First, to be fair, the flight was on time and the trip through the air was relatively smooth. But the flight was full, and they were checking carryons. As this process went on, the crew got increasingly rude and overbearing. During the drink service, a young girl (maybe 9) who had gotten up to use the lavatory got stuck behind the cart. At some point, she started feeling fearful and overwhelmed. Passengers noticed this and asked the crew to let her return to her seat. They refused. Then she started crying, and they still refused to move the cart forward to let her sit. The poor girl was trying to be brave and compose herself. The crew handled the situation terribly and with zero grace or decency. That episode, to me, encapsulates AA’s attitude toward its passengers. Disgraceful. The plane itself was cramped and miserable, as usual. There was zero inflight media or entertainment, other than the lane and borderline inappropriate jokes the steward made during the safety briefing. Then, of course, it took the better part of an hour for the checked bags to show up at the carousel. AA is no better than the el cheapo airlines these days and a far, far cry from its former self.

Early arrival. Great landing. Pilot updates. Too cold in plane.

Better to put road truck seat in plain it so uncomfortable can not adjustable and fill metal don’t have cushions at all it’s very hard to travel for five hours

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

food not having to pay for it, reclining seat would be nice, more leg room, HEAT!!!!!!!

An absolutely fraudulent experience. Extremely unprofessional. Terrible in all ways possible. Rude staff, flight attendants, and deceptive "policies."

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

The airline used deceptive tactics to charge us more for our trip. Search Frontier Class Action Lawsuit to find out more or read the hundreds of reviews that have nearly identical stories.. don't fly this airline.. you've been warned.

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

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