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Cheap flights from District of Columbia to Chicago from $76

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 10/31. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 4:56 pmIAD-ORD
11h 56m1 stop
Frontier Logo
6:30 pm - 12:11 amORD-IAD
28h 41m1 stop
$141Frontier
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Mon, Nov 3 - Thu, Nov 6
Frontier Logo
6:00 am - 11:05 pmIAD-MDW
18h 05m1 stop
Frontier Logo
6:00 am - 12:49 pmMDW-IAD
5h 49m1 stop
$141Frontier
Find Deal
Sat, Dec 6 - Mon, Dec 8
Multiple Airlines Logo
4:04 pm - 9:47 amIAD-ORD
18h 43m1 stop
Multiple Airlines Logo
5:11 am - 4:34 pmORD-IAD
10h 23m1 stop
$147Multiple Airlines
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Sun, Nov 2 - Thu, Nov 13
Multiple Airlines Logo
8:40 am - 8:27 pmIAD-ORD
12h 47m2 stops
Multiple Airlines Logo
6:00 am - 11:55 pmORD-IAD
16h 55m1 stop
$153Multiple Airlines
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Wed, Nov 5 - Sat, Nov 15
JetBlue Logo
4:55 pm - 8:52 pmDCA-ORD
4h 57m1 stop
JetBlue Logo
6:45 am - 2:36 pmORD-DCA
6h 51m1 stop
$203JetBlue
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Wed, Nov 5 - Wed, Nov 12
JetBlue Logo
6:15 am - 1:10 pmDCA-ORD
7h 55m1 stop
JetBlue Logo
2:05 pm - 10:47 pmORD-DCA
7h 42m1 stop
$208JetBlue
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Tue, Jan 27 - Sat, Jan 31
American Airlines Logo
11:55 am - 1:11 pmDCA-ORD
2h 16mnonstop
American Airlines Logo
9:45 am - 12:40 pmORD-DCA
1h 55mnonstop
$209American Airlines
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Mon, Nov 24 - Thu, Nov 27
Southwest Logo
6:00 am - 7:00 amDCA-MDW
2h 00mnonstop
Southwest Logo
7:20 am - 10:05 amMDW-DCA
1h 45mnonstop
$223Southwest
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Fri, Oct 31 - Sat, Nov 1
Southwest Logo
6:55 am - 1:15 pmDCA-MDW
7h 20m1 stop
Southwest Logo
7:20 am - 10:05 amMDW-DCA
1h 45mnonstop
$233Southwest
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Fri, Oct 31 - Sat, Nov 1
American Airlines Logo
1:44 pm - 5:44 pmDCA-ORD
5h 00m1 stop
American Airlines Logo
7:30 pm - 10:41 pmORD-DCA
2h 11mnonstop
$261American Airlines
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Sat, Nov 8 - Mon, Nov 10

JetBlue flights from District of Columbia to Chicago

Our best JetBlue deals on District of Columbia to Chicago flight tickets
JetBlue
Nov 5
DCA4:55 pmWashington, D.C. Reagan-National
4h 57m
1 stop
ORD8:52 pmChicago O'Hare Intl
Nov 12
ORD6:45 amChicago O'Hare Intl
6h 51m
1 stop
DCA2:36 pmWashington, D.C. Reagan-National
$203
Find similar
JetBlue
Jan 27
DCA6:15 amWashington, D.C. Reagan-National
7h 55m
1 stop
ORD1:10 pmChicago O'Hare Intl
Jan 31
ORD2:05 pmChicago O'Hare Intl
7h 42m
1 stop
DCA10:47 pmWashington, D.C. Reagan-National
$208
Find similar
JetBlue
Nov 5
DCA4:55 pmWashington, D.C. Reagan-National
4h 57m
1 stop
ORD8:52 pmChicago O'Hare Intl
Nov 10
ORD6:45 amChicago O'Hare Intl
6h 51m
1 stop
DCA2:36 pmWashington, D.C. Reagan-National
$212
Find similar

American Airlines flights from District of Columbia to Chicago

Our best American Airlines deals on District of Columbia to Chicago flight tickets
American Airlines
Nov 24
DCA11:55 amWashington, D.C. Reagan-National
2h 16m
ORD1:11 pmChicago O'Hare Intl
Nov 27
ORD9:45 amChicago O'Hare Intl
1h 55m
DCA12:40 pmWashington, D.C. Reagan-National
$209
Find similar
American Airlines
Nov 8
DCA1:44 pmWashington, D.C. Reagan-National
5h 00m
1 stop
ORD5:44 pmChicago O'Hare Intl
Nov 10
ORD7:30 pmChicago O'Hare Intl
2h 11m
DCA10:41 pmWashington, D.C. Reagan-National
$261
Find similar
American Airlines
Nov 17
DCA6:50 amWashington, D.C. Reagan-National
2h 39m
ORD8:29 amChicago O'Hare Intl
Nov 22
ORD1:10 pmChicago O'Hare Intl
2h 00m
DCA4:10 pmWashington, D.C. Reagan-National
$266
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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 October 8, 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 - ORD

IADORD

Washington, D.C. Dulles Intl

Mon 11/3

6:00 am-4:56 pm

1 stop11h 56m

Chicago O'Hare Intl

Thu 11/6

6:30 pm-12:11 am

1 stop28h 41m

$141

Washington, D.C.Chicago

IAD - MDW

IADMDW

Washington, D.C. Dulles Intl

Sat 12/6

6:00 am-11:05 pm

1 stop18h 05m

Chicago Midway

Mon 12/8

6:00 am-12:49 pm

1 stop5h 49m

$141

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Sun 11/2

4:04 pm-9:47 am

1 stop18h 43m

Chicago O'Hare Intl

Thu 11/13

5:11 am-4:34 pm

1 stop10h 23m

$147

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Wed 11/5

8:40 am-8:27 pm

2 stops12h 47m

Chicago O'Hare Intl

Sat 11/15

6:00 am-11:55 pm

1 stop16h 55m

$153

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 11/5

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Wed 11/12

6:45 am-2:36 pm

1 stop6h 51m

$203

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 1/27

6:15 am-1:10 pm

1 stop7h 55m

Chicago O'Hare Intl

Sat 1/31

2:05 pm-10:47 pm

1 stop7h 42m

$208

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 11/24

11:55 am-1:11 pm

Nonstop2h 16m

Chicago O'Hare Intl

Thu 11/27

9:45 am-12:40 pm

Nonstop1h 55m

$209

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 10/31

6:00 am-7:00 am

Nonstop2h 00m

Chicago Midway

Sat 11/1

7:20 am-10:05 am

Nonstop1h 45m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 10/31

6:55 am-1:15 pm

1 stop7h 20m

Chicago Midway

Sat 11/1

7:20 am-10:05 am

Nonstop1h 45m

$233

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 11/8

1:44 pm-5:44 pm

1 stop5h 00m

Chicago O'Hare Intl

Mon 11/10

7:30 pm-10:41 pm

Nonstop2h 11m

$261

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 $227.

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 $383. 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 $338. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $435.

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

Fly from Baltimore/Washington to Chicago O'Hare Intl 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 $329 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 10% 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

$160

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 $160. The best round-trip flight deal from District of Columbia to Chicago found on momondo in the last 72 hours is $291.
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)
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  • 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
8,082 reviews
Search Spirit Airlines flights
FrontierPriceFrom $69Free CancellationRating
5.8
3,145 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
7,969 reviews
Search Delta flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,236 reviews
Search Southwest flights
United AirlinesPriceFrom $159Free CancellationRating
7.4
8,965 reviews
Search United Airlines flights
American AirlinesPriceFrom $160Free 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