$87 Find Cheap Flights from Chicago to District of Columbia

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to District of Columbia departing on 8/22. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to District of Columbia, 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 Chicago to District of Columbia, as well as popular online travel agencies
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Cheap Flights from Chicago to District of Columbia

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Washington, D.C.
Baltimorenonstop$59
Washington, D.C.
Baltimorenonstop$59

Book Cheap Chicago to District of Columbia Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to District of Columbia 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 Chicago to District of Columbia

Sat, Sep 13 - Sat, Sep 20
Frontier Logo
10:51 am - 6:24 pmMDW-IAD
6h 33m1 stop
Frontier Logo
7:14 pm - 9:18 amIAD-MDW
15h 04m1 stop
$177Frontier
Find Deal
Sat, Sep 20 - Tue, Sep 30
Frontier Logo
10:51 am - 6:24 pmMDW-IAD
6h 33m1 stop
Frontier Logo
9:15 am - 3:58 pmIAD-MDW
7h 43m1 stop
$178Frontier
Find Deal
Wed, Sep 10 - Wed, Sep 10
American Airlines Logo
11:30 am - 2:24 pmORD-DCA
1h 54mnonstop
American Airlines Logo
3:28 pm - 7:05 pmDCA-ORD
4h 37m1 stop
$193American Airlines
Find Deal
Wed, Aug 20 - Thu, Aug 21
 Logo
11:36 am - 10:44 amORD-IAD
22h 08m2 stops
 Logo
4:56 pm - 9:21 amIAD-ORD
17h 25m2 stops
Sat, Sep 13 - Sun, Sep 14
 Logo
8:00 am - 6:24 pmORD-IAD
9h 24m1 stop
 Logo
9:03 am - 5:11 pmIAD-ORD
9h 08m1 stop
Wed, Aug 20 - Wed, Aug 20
American Airlines Logo
10:26 am - 3:55 pmORD-DCA
4h 29m1 stop
American Airlines Logo
6:00 pm - 7:26 pmDCA-ORD
2h 26mnonstop
$215American Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 2
United Airlines Logo
9:00 am - 11:59 amORD-DCA
1h 59mnonstop
United Airlines Logo
6:00 pm - 7:15 pmDCA-ORD
2h 15mnonstop
$217United Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
Southwest Logo
5:30 am - 8:20 amMDW-DCA
1h 50mnonstop
Southwest Logo
6:55 pm - 7:55 pmDCA-MDW
2h 00mnonstop
$217Southwest
Find Deal
Mon, Nov 3 - Wed, Nov 5
United Airlines Logo
12:45 pm - 3:38 pmORD-DCA
1h 53mnonstop
United Airlines Logo
5:00 pm - 6:23 pmDCA-ORD
2h 23mnonstop
$223United Airlines
Find Deal
Thu, Sep 11 - Sat, Sep 13
Southwest Logo
2:45 pm - 5:35 pmMDW-DCA
1h 50mnonstop
Southwest Logo
8:25 am - 9:25 amDCA-MDW
2h 00mnonstop
$223Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to District of Columbia flights

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

How much is a round-trip flight from Chicago to District of Columbia?

What is the cheapest Chicago to District of Columbia flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to District of Columbia.

The cheapest ticket to District of Columbia from Chicago found in the last 72 hours was to Baltimore, at $85 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Washington, D.C. Reagan-National Airport (DCA), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $153.

Can I save money by flying with a layover from Chicago to District of Columbia?

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 $374 on average.

What is the cheapest month to fly from Chicago to District of Columbia?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to District of Columbia, 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 Chicago to District of Columbia is August, when tickets cost $183 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $254 and $251 respectively.

What’s the cheapest day of the week to fly from Chicago to District of Columbia?

The average price of all round-trip flights from Chicago to District of Columbia clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to District of Columbia on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago to District of Columbia. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

How far in advance should I book a flight from Chicago to District of Columbia?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to District of Columbia, 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 Chicago to District of Columbia, you should book around 3 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.


Good to know

Low seasonFebruary
Cheapest flight$87
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Chicago Midway Airport to Washington Dulles Airport

FAQs - booking District of Columbia flights

  • How does KAYAK find such low prices on flights from Chicago to District of Columbia?

    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 Chicago to District of Columbia.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to District of Columbia?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to District of Columbia 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 Chicago to District of Columbia?

    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 from Chicago to District of Columbia with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to District of Columbia?

    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 from Chicago to District of Columbia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to District of Columbia?

    The cheapest time of day to fly to District of Columbia is generally in the morning, when round-trip flights cost $303 on average. Morning departures are around 37% cheaper than evening flights, on average. The most expensive time of day to fly to District of Columbia is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $650.

Reviews of the top 5 airlines serving from Chicago to District of Columbia

 
See real verified KAYAK customer reviews for airlines flying from Chicago to District of Columbia. 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 Chicago to District of Columbia? 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 4241 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

First time on Spirit. Definitely a streamline flight but I would fly Spirit again.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

We sat on the tarmac for an hour waiting for a gate to deplane.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Everything you need to know for your flight from Chicago to District of Columbia

Cabin class types available on flights to District of Columbia

Cabin classes available on flights to District of Columbia. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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