$72 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 2/21. 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

Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$160
Overall average: $346
Frontier
Sat 4/18Sun 4/19
DCA - ORD • 1 stop
Cheapest non-stop
$175
Typical prices: $244-$411
United Airlines
Sat 3/7Sat 3/14
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!
Flight Deals
Useful Info
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, Apr 18 - Sun, Apr 19
Frontier Logo
1:59 pm - 9:50 am
DCA
-
ORD
20h 51m
1 stop
Frontier Logo
10:55 am - 1:00 pm
ORD
-
DCA
25h 05m
1 stop
$160Frontier
Tue, Apr 7 - Tue, Apr 14
Frontier Logo
3:15 pm - 10:39 pm
IAD
-
ORD
8h 24m
1 stop
Frontier Logo
4:28 pm - 12:36 am
ORD
-
IAD
7h 08m
1 stop
$160Frontier
Sat, Apr 18 - Sat, Apr 25
Frontier Logo
10:51 am - 7:31 pm
IAD
-
MDW
9h 40m
1 stop
Frontier Logo
2:20 pm - 12:36 am
MDW
-
IAD
9h 16m
1 stop
$160Frontier
Tue, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
7:00 am - 12:40 am
IAD
-
ORD
18h 40m
2 stops
Multiple Airlines Logo
9:28 am - 11:56 pm
ORD
-
IAD
13h 28m
1 stop
$172Multiple Airlines
Sat, Mar 7 - Sat, Mar 14
United Airlines Logo
7:00 pm - 8:35 pm
DCA
-
ORD
2h 35mnonstop
United Airlines Logo
7:40 pm - 10:52 pm
ORD
-
DCA
2h 12mnonstop
$175United Airlines
Wed, Mar 4 - Sat, Mar 7
United Airlines Logo
3:30 pm - 4:51 pm
DCA
-
ORD
2h 21mnonstop
United Airlines Logo
7:00 am - 9:54 am
ORD
-
DCA
1h 54mnonstop
$177United Airlines
Sat, Feb 28 - Tue, Mar 3
American Airlines Logo
5:33 pm - 7:08 pm
DCA
-
ORD
2h 35mnonstop
American Airlines Logo
8:58 pm - 11:50 pm
ORD
-
DCA
1h 52mnonstop
$182American Airlines
Sat, Feb 28 - Wed, Apr 1
American Airlines Logo
3:21 pm - 4:45 pm
DCA
-
ORD
2h 24mnonstop
American Airlines Logo
11:50 am - 2:41 pm
ORD
-
DCA
1h 51mnonstop
$184American Airlines
Sat, Feb 28 - Wed, Apr 1
Southwest Logo
10:00 am - 11:10 am
DCA
-
MDW
2h 10mnonstop
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
DCA
1h 45mnonstop
$194Southwest
Tue, Apr 14 - Wed, Apr 15
Southwest Logo
7:00 pm - 8:05 pm
DCA
-
MDW
2h 05mnonstop
Southwest Logo
4:20 pm - 7:10 pm
MDW
-
DCA
1h 50mnonstop
$197Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$72
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 2% increase 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.
First Class flights to Chicagofrom $501
Business Class flights to Chicagofrom $507
Premium Economy Class flights to Chicagofrom $501
Economy Class flights to Chicagofrom $199