What airlines fly to Chicago?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Washington, D.C. Reagan-National Airport according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Washington, D.C. Reagan-National to Chicago?

United Airlines, Southwest, and Delta are the most popular carriers operating from Washington, D.C. Reagan-National to Chicago

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

The number of operators available for flights from Washington, D.C. Reagan-National Airport to Chicago is 4 as of July 2025.

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.

$47 Cheap Flights from Washington, D.C. Reagan-National Airport to Chicago in 2025

Q: How many flights depart from Washington, D.C. Reagan-National Airport to Chicago on average per week?

As of July 2025, 305 flights take off from Washington, D.C. Reagan-National Airport and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.

Q: How many flights depart from Washington, D.C. Reagan-National Airport to Chicago on average per day?

As of July 2025, there are 43 flights per day flying from Washington, D.C. Reagan-National Airport to Chicago. The most common time of day flights depart is 5:00PM, with 52% of flights taking off in the afternoon.

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Find the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

1:00 pm - 2:16 pmDCA-ORD

2h 16mnonstop

9:00 am - 11:59 amORD-DCA

1h 59mnonstop

$93United Airlines

Find Deal

mar., ago. 5 - mar., ago. 12

3:15 pm - 4:25 pmDCA-MDW

2h 10mnonstop

12:15 pm - 3:10 pmMDW-DCA

1h 55mnonstop

$93Southwest

Find Deal

mié., ago. 6 - mié., ago. 13

3:05 pm - 4:05 pmDCA-MDW

2h 00mnonstop

1:05 pm - 6:30 pmMDW-DCA

4h 25m1 stop

$103Southwest

Find Deal

lun., ago. 18 - sáb., ago. 23

3:30 pm - 4:46 pmDCA-ORD

2h 16mnonstop

8:00 am - 10:56 amORD-DCA

1h 56mnonstop

$106United Airlines

Find Deal

jue., ago. 14 - dom., ago. 17

11:55 am - 12:50 pmDCA-MDW

1h 55mnonstop

5:25 am - 8:15 amMDW-DCA

1h 50mnonstop

$106Southwest

Find Deal

jue., sep. 11 - dom., sep. 14

10:09 pm - 11:25 pmDCA-ORD

2h 16mnonstop

8:41 pm - 11:50 pmORD-DCA

2h 09mnonstop

$108American Airlines

Find Deal

vie., ago. 15 - mar., ago. 19

11:55 am - 12:50 pmDCA-MDW

1h 55mnonstop

8:05 am - 2:55 pmMDW-DCA

5h 50m2 stops

$108Southwest

Find Deal

lun., ago. 18 - sáb., ago. 23

12:10 pm - 1:29 pmDCA-ORD

2h 19mnonstop

8:45 pm - 11:57 pmORD-DCA

2h 12mnonstop

$117American Airlines

Find Deal

mar., ago. 5 - mar., ago. 5

6:00 pm - 7:26 pmDCA-ORD

2h 26mnonstop

8:41 pm - 11:50 pmORD-DCA

2h 09mnonstop

$120American Airlines

Find Deal

vie., ago. 22 - vie., ago. 29

6:00 pm - 7:26 pmDCA-ORD

2h 26mnonstop

5:21 pm - 8:16 pmORD-DCA

1h 55mnonstop

$121American Airlines

Find Deal

vie., ago. 22 - vie., ago. 29

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

Our best American Airlines deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets

American Airlines

Aug 15

DCA10:09 pmWashington, D.C. Reagan-National

2h 16m

ORD11:25 pmChicago O'Hare Intl

Aug 19

ORD8:41 pmChicago O'Hare Intl

2h 09m

DCA11:50 pmWashington, D.C. Reagan-National

$108

Find similar

American Airlines

Aug 5

DCA12:10 pmWashington, D.C. Reagan-National

2h 19m

ORD1:29 pmChicago O'Hare Intl

Aug 5

ORD8:45 pmChicago O'Hare Intl

2h 12m

DCA11:57 pmWashington, D.C. Reagan-National

$117

Find similar

American Airlines

Aug 22

DCA6:00 pmWashington, D.C. Reagan-National

2h 26m

ORD7:26 pmChicago O'Hare Intl

Aug 29

ORD8:41 pmChicago O'Hare Intl

2h 09m

DCA11:50 pmWashington, D.C. Reagan-National

$120

Find similar

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

Our best United Airlines deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets

United Airlines

Aug 5

DCA1:00 pmWashington, D.C. Reagan-National

2h 16m

ORD2:16 pmChicago O'Hare Intl

Aug 12

ORD9:00 amChicago O'Hare Intl

1h 59m

DCA11:59 amWashington, D.C. Reagan-National

$93

Find similar

United Airlines

Aug 14

DCA3:30 pmWashington, D.C. Reagan-National

2h 16m

ORD4:46 pmChicago O'Hare Intl

Aug 17

ORD8:00 amChicago O'Hare Intl

1h 56m

DCA10:56 amWashington, D.C. Reagan-National

$106

Find similar

United Airlines

Aug 22

DCA2:00 pmWashington, D.C. Reagan-National

2h 13m

ORD3:13 pmChicago O'Hare Intl

Aug 24

ORD8:00 amChicago O'Hare Intl

1h 58m

DCA10:58 amWashington, D.C. Reagan-National

$119

Find similar

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

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Washington, D.C. Reagan-National Airport, with most prices found around $263. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during February average around $267.

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 $386. 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 $491.

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 $334. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $439.

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 $307 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 $249 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 July 2025, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 34% 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	$47
Fastest flight time	1h 55m
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 $47. The best round-trip flight deal from Washington, D.C. Reagan-National Airport to Chicago found on momondo in the last 72 hours is $93.

The fastest flight from Washington, D.C. Reagan-National Airport to Chicago takes 1h 55m

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)

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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 1h 55m 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?
The number of operators available for flights from Washington, D.C. Reagan-National Airport to Chicago is 4 as of July 2025.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Washington, D.C. Reagan-National Airport to Chicago is Airbus A319 (14.02% of total bookings). The next most popular plane models are Boeing 737-800 (13.71%), Airbus A320-100/200 (12.55%), and Boeing 737 MAX 8 (9.77%).
What is the most popular airline from Washington, D.C. Reagan-National Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Washington, D.C. Reagan-National Airport to Chicago is American Airlines (42% of total bookings). The next most popular airlines are United Airlines (30%), Southwest (26%), and Frontier (1%).

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
Frontier	PriceFrom $120	Free Cancellation	Rating 5.9 3,271 reviews	Search Frontier flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $177	Free Cancellation	Rating 8.0 4,249 reviews	Search Southwest flights
United Airlines	PriceFrom $190	Free Cancellation	Rating 7.4 8,846 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 33 times per week, with 4,249 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 $177 (round-trip), much lower than the average airfare cost of $300 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. Reagan-National Airport to Chicago
United Airlines (7.4/10 from 8,846 reviews) operates around 56 flights from Washington, D.C. Reagan-National Airport to Chicago in any given week. The average United Airlines airfare for this route is around $329, with deals from around $190 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.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Monticello

Chesterton

Porter

Griffith

Saint John

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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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Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $47

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

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

Our best United Airlines deals on Washington, D.C. Reagan-National Airport to Chicago flight tickets

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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?

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

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

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?

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 July 2025, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 34% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Washington, D.C. Reagan-National to Chicago?

United Airlines, Southwest, and Delta are the most popular carriers operating from Washington, D.C. Reagan-National to Chicago

What airlines fly to Chicago?

How many flights depart from Washington, D.C. Reagan-National Airport to Chicago on average per day?

As of July 2025, there are 43 flights per day flying from Washington, D.C. Reagan-National Airport to Chicago. The most common time of day flights depart is 5:00PM, with 52% of flights taking off in the afternoon.

How many flights depart from Washington, D.C. Reagan-National Airport to Chicago on average per week?

As of July 2025, 305 flights take off from Washington, D.C. Reagan-National Airport and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.

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

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

Fastest flight time

Direct flights

Airports in Chicago

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

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

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?

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

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

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

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

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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