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Cheap flights from District of Columbia to Chicago from $73

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from District of Columbia to Chicago departing on 2/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:58 pm - 8:46 amIAD-MDW
14h 48m1 stop
Frontier Logo
8:15 am - 6:16 pmMDW-IAD
9h 01m1 stop
$146Frontier
Find Deal
Mon, Dec 15 - Mon, Dec 22
Frontier Logo
5:42 pm - 10:17 pmIAD-MDW
5h 35m1 stop
Frontier Logo
4:31 pm - 9:08 amMDW-IAD
15h 37m1 stop
$152Frontier
Find Deal
Wed, Jan 7 - Fri, Jan 9
Frontier Logo
6:00 am - 11:31 amIAD-MDW
6h 31m1 stop
Frontier Logo
6:10 am - 3:27 pmMDW-IAD
8h 17m1 stop
$154Frontier
Find Deal
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
6:00 am - 11:31 amIAD-MDW
6h 31m1 stop
Frontier Logo
6:10 am - 3:27 pmMDW-IAD
8h 17m1 stop
$155Frontier
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
6:00 am - 5:00 pmIAD-ORD
12h 00m2 stops
Multiple Airlines Logo
5:50 am - 4:46 pmORD-IAD
9h 56m1 stop
$166Multiple Airlines
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Wed, Jan 7 - Fri, Jan 9
JetBlue Logo
1:00 pm - 5:43 pmDCA-ORD
5h 43m1 stop
JetBlue Logo
6:45 am - 1:20 pmORD-DCA
5h 35m1 stop
$172JetBlue
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Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
9:00 am - 8:01 pmIAD-ORD
12h 01m2 stops
Multiple Airlines Logo
11:44 am - 11:05 pmORD-IAD
10h 21m1 stop
$174Multiple Airlines
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Wed, Dec 10 - Mon, Dec 15
JetBlue Logo
1:00 pm - 5:43 pmDCA-ORD
5h 43m1 stop
JetBlue Logo
6:45 am - 1:20 pmORD-DCA
5h 35m1 stop
$179JetBlue
Find Deal
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
8:45 pm - 9:55 pmDCA-MDW
2h 10mnonstop
Southwest Logo
8:10 pm - 10:55 pmMDW-DCA
1h 45mnonstop
$237Southwest
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Wed, Dec 24 - Wed, Dec 31
Southwest Logo
9:30 am - 10:35 amDCA-MDW
2h 05mnonstop
Southwest Logo
8:35 pm - 11:20 pmMDW-DCA
1h 45mnonstop
$241Southwest
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Thu, Dec 25 - Tue, Jan 6

JetBlue flights from District of Columbia to Chicago

Our best JetBlue deals on District of Columbia to Chicago flight tickets
JetBlue
Jan 8
DCA1:00 pmWashington, D.C. Reagan-National
5h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jan 12
ORD6:45 amChicago O'Hare Intl
5h 35m
1 stop
DCA1:20 pmWashington, D.C. Reagan-National
$172
Find similar
JetBlue
Jan 8
DCA1:00 pmWashington, D.C. Reagan-National
5h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jan 12
ORD6:45 amChicago O'Hare Intl
5h 35m
1 stop
DCA1:20 pmWashington, D.C. Reagan-National
$179
Find similar
JetBlue
Jan 8
DCA10:00 amWashington, D.C. Reagan-National
8h 44m
1 stop
ORD5:44 pmChicago O'Hare Intl
Jan 15
ORD7:45 amChicago O'Hare Intl
5h 49m
1 stop
DCA2:34 pmWashington, D.C. Reagan-National
$184
Find similar

United Airlines flights from District of Columbia to Chicago

Our best United Airlines deals on District of Columbia to Chicago flight tickets
United Airlines
Dec 10
DCA12:00 pmWashington, D.C. Reagan-National
2h 12m
ORD1:12 pmChicago O'Hare Intl
Dec 13
ORD9:00 amChicago O'Hare Intl
1h 58m
DCA11:58 amWashington, D.C. Reagan-National
$231
Find similar
United Airlines
Dec 24
DCA6:00 pmWashington, D.C. Reagan-National
2h 17m
ORD7:17 pmChicago O'Hare Intl
Jan 1
ORD7:00 amChicago O'Hare Intl
1h 59m
DCA9:59 amWashington, D.C. Reagan-National
$237
Find similar
United Airlines
Dec 10
DCA9:05 amWashington, D.C. Reagan-National
5h 04m
1 stop
ORD1:09 pmChicago O'Hare Intl
Dec 13
ORD9:05 pmChicago O'Hare Intl
1h 54m
DCA11:59 pmWashington, D.C. Reagan-National
$241
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from District of Columbia to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 25, 2025.
Use the filters below to find and compare flights from District of Columbia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Mon 12/15

6:58 pm-8:46 am

1 stop14h 48m

Chicago Midway

Mon 12/22

8:15 am-6:16 pm

1 stop9h 01m

$146

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Wed 1/7

5:42 pm-10:17 pm

1 stop5h 35m

Chicago Midway

Fri 1/9

4:31 pm-9:08 am

1 stop15h 37m

$152

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

Mon 1/12

6:10 am-3:27 pm

1 stop8h 17m

$154

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Thu 1/8

6:00 am-11:31 am

1 stop6h 31m

Chicago Midway

Mon 1/12

6:10 am-3:27 pm

1 stop8h 17m

$155

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 1/7

6:00 am-5:00 pm

2 stops12h 00m

Chicago O'Hare Intl

Fri 1/9

5:50 am-4:46 pm

1 stop9h 56m

$166

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 1/8

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

Mon 1/12

6:45 am-1:20 pm

1 stop5h 35m

$172

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 12/10

9:00 am-8:01 pm

2 stops12h 01m

Chicago O'Hare Intl

Mon 12/15

11:44 am-11:05 pm

1 stop10h 21m

$174

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 1/8

1:00 pm-5:43 pm

1 stop5h 43m

Chicago O'Hare Intl

Mon 1/12

6:45 am-1:20 pm

1 stop5h 35m

$179

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/24

8:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Wed 12/31

8:10 pm-10:55 pm

Nonstop1h 45m

$237

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 12/25

9:30 am-10:35 am

Nonstop2h 05m

Chicago Midway

Tue 1/6

8:35 pm-11:20 pm

Nonstop1h 45m

$241

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from District of Columbia to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from District of Columbia, with most prices found around $203. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from District of Columbia to Chicago during February average around $224.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $381. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from District of Columbia to Chicago for around $501.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from District of Columbia to Chicago during this time can be as low as $343. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $433.

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

Fly from Baltimore/Washington to Chicago Midway for the best District of Columbia - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from District of Columbia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $331 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from District of Columbia for as low as $216 on momondo.

What cabin class options are available on District of Columbia to Chicago flights?

There are 4 cabin classes available to choose from on District of Columbia to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on District of Columbia to Chicago flights?

You could potentially save up to 29% on your flight if you consider stops on a District of Columbia to Chicago flight.

Cheap District of Columbia to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from District of Columbia to Chicago

Best Price Found

$166

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from District of Columbia in the past 72 hours is $166. The best round-trip flight deal from District of Columbia to Chicago found on momondo in the last 72 hours is $296.
The fastest flight from District of Columbia to Chicago takes 2h 00m
Direct flights go from District of Columbia to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • When did momondo last update prices for flights from District of Columbia to Chicago?

    Prices for flights from District of Columbia to Chicago are updated daily.

  • How many operators does momondo search for flights from District of Columbia to Chicago?

  • How old do you have to be to fly from District of Columbia to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from District of Columbia to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from District of Columbia to Chicago?

Best airlines flying from District of Columbia to Chicago

Compare and see reviews for airlines that fly from District of Columbia to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $52Free CancellationRating
6.3
8,157 reviews
Search Spirit Airlines flights
FrontierPriceFrom $69Free CancellationRating
5.8
3,097 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
7,998 reviews
Search Delta flights
SouthwestPriceFrom $156Free CancellationRating
8.0
4,252 reviews
Search Southwest flights
United AirlinesPriceFrom $158Free CancellationRating
7.4
9,044 reviews
Search United Airlines flights
American AirlinesPriceFrom $166Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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

Why use momondo?

Why should I use momondo to find a flight deal from District of Columbia to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from District of Columbia to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from District of Columbia to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from District of Columbia with this policy.

How can momondo help me find flights from District of Columbia to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from District of Columbia to Chicago.

I’m not ready to book a flight from District of Columbia to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for District of Columbia to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport