$107 Find Cheap Flights from District of Columbia 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 to Chicago departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from District of Columbia to Chicago

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

Sat, May 9 - Sat, May 16
United Airlines Logo
4:55 pm - 6:15 pm
DCA
-
ORD
2h 20mnonstop
United Airlines Logo
7:45 pm - 10:47 pm
ORD
-
DCA
2h 02mnonstop
$219United Airlines
Sat, May 2 - Mon, May 4
United Airlines Logo
5:15 pm - 6:33 pm
IAD
-
ORD
2h 18mnonstop
United Airlines Logo
9:35 pm - 12:33 am
ORD
-
IAD
1h 58mnonstop
$219United Airlines
Sat, May 2 - Tue, May 5
Southwest Logo
12:15 pm - 2:45 pm
DCA
-
MDW
3h 30m
1 stop
Southwest Logo
3:00 pm - 11:00 pm
MDW
-
DCA
7h 00m
2 stops
$219Southwest
Thu, May 7 - Mon, May 11
American Airlines Logo
1:46 pm - 3:10 pm
DCA
-
ORD
2h 24mnonstop
American Airlines Logo
9:01 pm - 11:57 pm
ORD
-
DCA
1h 56mnonstop
$220American Airlines
Sat, May 2 - Mon, May 4
Frontier Logo
10:51 am - 6:37 pm
IAD
-
MDW
8h 46m
1 stop
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$220Frontier
Tue, May 19 - Tue, May 26
Frontier Logo
6:37 pm - 11:13 pm
IAD
-
ORD
29h 36m
1 stop
Frontier Logo
8:05 am - 6:42 pm
ORD
-
IAD
9h 37m
1 stop
$221Frontier
Thu, May 7 - Tue, May 12
American Airlines Logo
5:00 am - 8:30 am
DCA
-
ORD
4h 30m
1 stop
American Airlines Logo
6:08 am - 9:05 am
ORD
-
DCA
1h 57mnonstop
$222American Airlines
Wed, Apr 29 - Mon, May 4
Southwest Logo
1:00 pm - 6:25 pm
DCA
-
ORD
6h 25m
1 stop
Southwest Logo
2:40 pm - 11:00 pm
ORD
-
DCA
7h 20m
2 stops
$223Southwest
Mon, May 4 - Thu, May 7
Multiple Airlines Logo
7:43 pm - 7:55 am
IAD
-
ORD
13h 12m
1 stop
Multiple Airlines Logo
7:33 pm - 3:14 pm
ORD
-
IAD
18h 41m
2 stops
$223Multiple Airlines
Fri, May 15 - Tue, May 19
Multiple Airlines Logo
2:52 pm - 11:13 pm
IAD
-
ORD
9h 21m
2 stops
Multiple Airlines Logo
6:55 am - 4:21 pm
ORD
-
IAD
8h 26m
1 stop
$229Multiple Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$107
Best time to beat the crowds with an average 10% drop in price.
Flight from Washington Dulles Airport to Chicago Midway Airport

FAQs for booking flights from District of Columbia to Chicago

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

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from District of Columbia 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 District of Columbia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

Everything you need to know for your flight to Chicago

Cabin class types available on flights to District of Columbia

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