How long is the flight from Washington, D.C. Reagan-National Airport to Chicago?

Departing from Washington, D.C. Reagan-National Airport to Chicago will take you 2h 05m. Airlines will cover a distance of 599 mi. This flight may include one or multiple stops.

What are the cheapest airlines flying from Washington, D.C. Reagan-National Airport to Chicago round-trip?

Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $101. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $169 and $179, respectively. Frontier is 65% cheaper than the average price of flights available within the next 90 days to this destination.

How far ahead should I book a flight from Washington, D.C. Reagan-National Airport to Chicago?

The best time to book flights from Washington, D.C. Reagan-National Airport to Chicago is 88 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago?

Currently, July is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $99). Flying from Washington, D.C. Reagan-National Airport to Chicago in December is currently the most expensive (average of $197). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from Washington, D.C. Reagan-National Airport to Chicago?

Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Washington, D.C. Reagan-National Airport to Chicago?

The most popular flight routes from Washington, D.C. Reagan-National Airport to Chicago are Washington, D.C. Reagan-National - Chicago O'Hare Intl, Washington, D.C. Reagan-National - Chicago Midway and Washington, D.C. Reagan-National - Chicago Greater Rockford.

What are the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago?

While on average a flight from Washington, D.C. Reagan-National Airport to Chicago is generally $908, our data shows the cheapest flight currently is $125. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $110 for that flight.

What are the most reliable airlines from Washington, D.C. Reagan-National Airport to Chicago?

Before booking your flight to Chicago from Washington, D.C. Reagan-National Airport, check out the most reliable airlines to get you to your destination on time: Envoy Air (100%), Cathay Pacific (90%), Royal Jordanian( 84%).

What are the most popular airlines that fly from Washington, D.C. Reagan-National Airport to Chicago?

Consider American Airlines, United Airlines or Southwest when booking your flight. These represent the most popular airlines when flying from Washington, D.C. Reagan-National Airport to Chicago.

What is the cheapest time of day to fly from DCA to CHI?

It’s typically best to fly out from Washington, D.C. Reagan-National Airport to Chicago in the evening. Doing so could potentially save you 16% on the flight price compared to flying at noon, which is usually more expensive.

Most accurate provider : When it comes to deals on Washington, D.C. Reagan-National Airport-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Washington, D.C. Reagan-National Airport-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Washington, D.C. Reagan-National Airport-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Washington, D.C. Reagan-National Airport-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C. Reagan-National Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Can I find deals for flights from Reagan-National to Chicago that include hotel bookings?

Yes. In addition to deals on Reagan-National to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Reagan-National to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Reagan-National to Chicago.

Can I find deals for business class flights from Reagan-National to Chicago?

Yes. Cheapflights offers flight deals from Reagan-National to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$78+ Flights from Washington, D.C. Reagan-National Airport to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$143 (CheapOair)
One-way from	$78 (Trip.com)
Popular in	December
Cheapest in	February
Average price	$299
Good round-trip deal	$297 or less
Good one-way deal	$158 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars

DCA

Reserve parking online at DCA to ensure availability, especially during busy times. Parking Garage 1 serves Terminal 1, and Garage 2 serves Terminal 2.

ORD

Take the “L” train from ORD to avoid traffic and reach downtown Chicago efficiently.

MDW

Use the Orange Line train for a quick, affordable trip from MDW to downtown Chicago in under 30 minutes.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$101	Average$182	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$169	Average$298	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$179	Average$309	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$200	Average$328	FlexibilityNo cancel fee	On-time69%

$78+ Cheap flights from Reagan-National (DCA) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/9. Fares are subject to change and may not be available on all flights or dates of travel.

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Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago are usually found in February or May, booked 88 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Reagan-National to Chicago

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Cheapest flights from Reagan-National to ChicagoExplore the most affordable flight options available from Reagan-National to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

Explore the most affordable flight options available from Reagan-National to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

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Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Reagan-National to Chicago in October.

Best time to book a flight from Reagan-National to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Reagan-National with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. Reagan-National Airport to Chicago

How far ahead should I book a flight from Washington, D.C. Reagan-National Airport to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Reagan-National to Chicago. Price data was last updated on October 24, 2025.

What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago?

What is the cheapest time of day to fly from DCA to CHI?

Find hourly flight availability from Reagan-National to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 30, 2025.

What is the cheapest day to fly from Washington, D.C. Reagan-National Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Reagan-National to Chicago. Price data was last updated on October 26, 2025.

The best insider tips for Washington, D.C. Reagan-National Airport to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago trip

Airports

DCA

ORD

MDW

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Related info for your journey

Find useful and relevant information for your journey from Reagan-National to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

How long is the flight from Washington, D.C. Reagan-National Airport to Chicago?

What are the cheapest airlines flying from Washington, D.C. Reagan-National Airport to Chicago round-trip?

What are the most popular routes from Washington, D.C. Reagan-National Airport to Chicago?

What are the most reliable airlines from Washington, D.C. Reagan-National Airport to Chicago?

What are the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago?

Can I find deals for flights from Reagan-National to Chicago that include hotel bookings?

How can I find direct flights from Reagan-National to Chicago?

Can I find deals for business class flights from Reagan-National to Chicago?

What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago?

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Cheapest flights from Reagan-National to Chicago
Explore the most affordable flight options available from Reagan-National to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.