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Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $80

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. Reagan-National Airport to Chicago departing on 11/1. 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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Find the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
2:00 pm - 12:12 amDCA-ORD
11h 12m1 stop
Frontier Logo
7:15 am - 9:59 pmORD-DCA
13h 44m1 stop
$160Frontier
Find Deal
Wed, Oct 29 - Sat, Nov 1
Frontier Logo
8:00 am - 12:12 amDCA-ORD
17h 12m1 stop
Frontier Logo
7:15 am - 4:59 pmORD-DCA
8h 44m1 stop
$162Frontier
Find Deal
Tue, Oct 28 - Sat, Nov 1
JetBlue Logo
4:55 pm - 8:52 pmDCA-ORD
4h 57m1 stop
JetBlue Logo
6:45 am - 2:50 pmORD-DCA
7h 05m1 stop
$203JetBlue
Find Deal
Tue, Nov 4 - Wed, Nov 5
JetBlue Logo
4:55 pm - 8:52 pmDCA-ORD
4h 57m1 stop
JetBlue Logo
6:45 am - 2:36 pmORD-DCA
6h 51m1 stop
$207JetBlue
Find Deal
Sat, Nov 8 - Mon, Nov 10
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
Find Deal
Mon, Nov 24 - Thu, Nov 27
Southwest Logo
6:55 am - 1:05 pmDCA-MDW
7h 10m1 stop
Southwest Logo
5:25 pm - 8:15 pmMDW-DCA
1h 50mnonstop
$233Southwest
Find Deal
Thu, Dec 25 - Wed, Jan 7
United Airlines Logo
12:00 pm - 1:11 pmDCA-ORD
2h 11mnonstop
United Airlines Logo
9:15 am - 2:35 pmORD-DCA
4h 20m1 stop
$233United Airlines
Find Deal
Fri, Oct 31 - Tue, Nov 4
Southwest Logo
8:45 pm - 9:55 pmDCA-MDW
2h 10mnonstop
Southwest Logo
9:15 am - 12:00 pmMDW-DCA
1h 45mnonstop
$236Southwest
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Thu, Nov 20 - Mon, Nov 24
United Airlines Logo
6:30 am - 7:45 amDCA-ORD
2h 15mnonstop
United Airlines Logo
10:00 am - 12:59 pmORD-DCA
1h 59mnonstop
$236United Airlines
Find Deal
Mon, Nov 24 - Tue, Dec 2
American Airlines Logo
6:00 am - 7:21 amDCA-ORD
2h 21mnonstop
American Airlines Logo
6:06 am - 8:59 amORD-DCA
1h 53mnonstop
$239American Airlines
Find Deal
Mon, Nov 24 - Wed, Nov 26

JetBlue flights from Washington, D.C. Reagan-National Airport to Chicago

Our best JetBlue deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets
JetBlue
Nov 4
DCA4:55 pmWashington, D.C. Reagan-National
4h 57m
1 stop
ORD8:52 pmChicago O'Hare Intl
Nov 5
ORD6:45 amChicago O'Hare Intl
7h 05m
1 stop
DCA2:50 pmWashington, D.C. Reagan-National
$203
Find similar
JetBlue
Nov 8
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
$207
Find similar
JetBlue
Nov 24
DCA5:43 pmWashington, D.C. Reagan-National
6h 07m
1 stop
ORD10:50 pmChicago O'Hare Intl
Nov 27
ORD8:20 amChicago O'Hare Intl
5h 39m
1 stop
DCA2:59 pmWashington, D.C. Reagan-National
$213
Find similar

Frontier flights from Washington, D.C. Reagan-National Airport to Chicago

Our best Frontier deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets
Frontier
Oct 29
DCA2:00 pmWashington, D.C. Reagan-National
11h 12m
1 stop
ORD12:12 amChicago O'Hare Intl
Nov 1
ORD7:15 amChicago O'Hare Intl
13h 44m
1 stop
DCA9:59 pmWashington, D.C. Reagan-National
$160
Find similar
Frontier
Oct 28
DCA8:00 amWashington, D.C. Reagan-National
17h 12m
1 stop
ORD12:12 amChicago O'Hare Intl
Nov 1
ORD7:15 amChicago O'Hare Intl
8h 44m
1 stop
DCA4:59 pmWashington, D.C. Reagan-National
$162
Find similar
Frontier
Nov 13
DCA6:00 pmWashington, D.C. Reagan-National
7h 15m
1 stop
ORD12:15 amChicago O'Hare Intl
Nov 17
ORD6:00 amChicago O'Hare Intl
14h 59m
1 stop
DCA9:59 pmWashington, D.C. Reagan-National
$166
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Washington, D.C. Reagan-National Airport 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 14, 2025.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 10/29

2:00 pm-12:12 am

1 stop11h 12m

Chicago O'Hare Intl

Sat 11/1

7:15 am-9:59 pm

1 stop13h 44m

$160

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 10/28

8:00 am-12:12 am

1 stop17h 12m

Chicago O'Hare Intl

Sat 11/1

7:15 am-4:59 pm

1 stop8h 44m

$162

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 11/4

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Wed 11/5

6:45 am-2:50 pm

1 stop7h 05m

$203

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 11/8

4:55 pm-8:52 pm

1 stop4h 57m

Chicago O'Hare Intl

Mon 11/10

6:45 am-2:36 pm

1 stop6h 51m

$207

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

Thu 12/25

6:55 am-1:05 pm

1 stop7h 10m

Chicago Midway

Wed 1/7

5:25 pm-8:15 pm

Nonstop1h 50m

$233

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Fri 10/31

12:00 pm-1:11 pm

Nonstop2h 11m

Chicago O'Hare Intl

Tue 11/4

9:15 am-2:35 pm

1 stop4h 20m

$233

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 11/20

8:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Mon 11/24

9:15 am-12:00 pm

Nonstop1h 45m

$236

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 11/24

6:30 am-7:45 am

Nonstop2h 15m

Chicago O'Hare Intl

Tue 12/2

10:00 am-12:59 pm

Nonstop1h 59m

$236

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 11/24

6:00 am-7:21 am

Nonstop2h 21m

Chicago O'Hare Intl

Wed 11/26

6:06 am-8:59 am

Nonstop1h 53m

$239

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 Washington, D.C. Reagan-National Airport 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 February is, on average, the cheapest month to fly to Chicago from Washington, D.C. Reagan-National Airport, with most prices found around $267. If you’re not able to fly to Chicago in February, then May is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during May average around $273.

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 Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport to Chicago during this time can be as low as $337. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $436.

What is the cheapest Washington, D.C. Reagan-National to Chicago flight route?

Fly from Washington, D.C. Reagan-National to Chicago Midway for the best Washington, D.C. Reagan-National - 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 Washington, D.C. Reagan-National Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $309 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. Reagan-National Airport for as low as $250 on momondo.

What cabin class options are available on Washington, D.C. Reagan-National to Chicago flights?

There are 4 cabin classes available to choose from on Washington, D.C. Reagan-National to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Washington, D.C. Reagan-National Airport to Chicago flight prices changed over time?

As of October 2025, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 12% cheaper when compared to flights at the same time last year.

When to book flights from Washington, D.C. Reagan-National Airport to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. Reagan-National Airport to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Washington, D.C. Reagan-National Airport to Chicago (DCA to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. Reagan-National Airport to Chicago

Best Price Found

$161

Fastest flight time

2h 00m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Washington, D.C. Reagan-National Airport in the past 72 hours is $161. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $289.
The fastest flight from Washington, D.C. Reagan-National Airport to Chicago takes 2h 00m
Direct flights go from Washington, D.C. Reagan-National Airport to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Washington, D.C. Reagan-National to Chicago by plane?

    There are 594.5 mi between Washington, D.C. Reagan-National and Chicago. Typically, this will take 2h 00m by plane in normal conditions.

  • When did momondo last update prices for flights from Washington, D.C. Reagan-National Airport to Chicago?

    Prices for flights from Washington, D.C. Reagan-National Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Washington, D.C. Reagan-National Airport to Chicago?

  • How old do you have to be to fly from Washington, D.C. Reagan-National Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Reagan-National Airport to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Washington, D.C. Reagan-National Airport to Chicago?

  • What is the most popular airline from Washington, D.C. Reagan-National Airport to Chicago?

Best airlines flying from Washington, D.C. Reagan-National Airport to Chicago

Compare and see reviews for airlines that fly from Washington, D.C. Reagan-National Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $101Free CancellationRating
5.8
3,135 reviews
Search Frontier flights
American AirlinesPriceFrom $169Free CancellationRating
7.2
11,042 reviews
Search American Airlines flights
SouthwestPriceFrom $179Free CancellationRating
8.0
4,238 reviews
Search Southwest flights
United AirlinesPriceFrom $198Free CancellationRating
7.4
8,976 reviews
Search United Airlines flights

  • Southwest Flights From Washington, D.C. Reagan-National Airport to Chicago

    Southwest flies from Washington, D.C. Reagan-National Airport to Chicago around 34 times per week, with 4,238 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. Reagan-National Airport to Chicago in the last 72 hours was $179 (round-trip), much lower than the average airfare cost of $310 for Southwest flights on this route.

  • United Airlines Flights From Washington, D.C. Reagan-National Airport to Chicago

    United Airlines (7.4/10 from 8,976 reviews) operates around 65 flights from Washington, D.C. Reagan-National Airport to Chicago in any given week. The average United Airlines airfare for this route is around $332, with deals from around $198 rare but found on momondo. Referenced prices are for round-trip Washington, D.C. Reagan-National Airport to Chicago flight searches in the last 72 hours.

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 Washington, D.C. to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Washington, D.C. to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Washington, D.C. which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Washington, D.C. to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Washington, D.C.. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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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