Cheap Flights from Washington Ronald Reagan to Chicago

Compare Washington Ronald Reagan to Chicago flight deals

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Flight deals from Washington Ronald Reagan Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Washington Ronald Reagan Airport to Chicago? If you want to travel next month, return fares start from $339. Find the lowest prices on one-way and return tickets right here.

Chicago.$267 per passenger.Departing Thu, 16 Apr, returning Mon, 20 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Ronald Reagan on Thu, 16 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 20 Apr, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $267, select.

Chicago.$269 per passenger.Departing Wed, 29 Apr, returning Mon, 4 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Ronald Reagan on Wed, 29 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 4 May, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $269, select.

Chicago.$326 per passenger.Departing Tue, 24 Feb, returning Tue, 3 Mar.Return flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Tue, 24 Feb, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 3 Mar, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $326, select.

Chicago.$327 per passenger.Departing Tue, 10 Mar, returning Tue, 17 Mar.Return flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Tue, 10 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 17 Mar, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $327, select.

Chicago.$327 per passenger.Departing Tue, 31 Mar, returning Tue, 7 Apr.Return flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Tue, 31 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 7 Apr, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $327, select.

Chicago.$339 per passenger.Departing Sat, 9 May, returning Sat, 16 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 9 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 16 May, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $339, select.

Chicago.$339 per passenger.Departing Sat, 7 Feb, returning Thu, 12 Feb.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Ronald Reagan on Sat, 7 Feb, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 12 Feb, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $339, select.

Chicago.$354 per passenger.Departing Wed, 25 Feb, returning Sat, 28 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Wed, 25 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 28 Feb, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $354, select.

Chicago.$385 per passenger.Departing Mon, 13 Apr, returning Wed, 15 Apr.Return flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Mon, 13 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 15 Apr, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $385, select.

Chicago.$406 per passenger.Departing Mon, 27 Apr, returning Mon, 4 May.Return flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Mon, 27 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 4 May, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $406, select.

Find the cheapest month to fly from Washington Ronald Reagan to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Washington Ronald Reagan to Chicago flights are currently cheapest in April.

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Direct flights from Washington Ronald Reagan to Chicago

Alternative Washington Ronald Reagan to Chicago routes

Looking for the cheapest, fastest or easiest route from Washington Ronald Reagan to Chicago? You could fly into the following airports instead.

Washington D.C. to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$267
Cheapest month to fly	April
Average flight time	2 hrs, 15 mins
Most popular airline	British Airways
Average flights per week	1,320

Finding cheap flights from Washington Ronald Reagan to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Washington Ronald Reagan to Chicago?

The best price we found for a return flight from Washington Ronald Reagan to Chicago is $267. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Washington Ronald Reagan to Chicago?

2 hours and 15 minutes is the average flight time from Washington Ronald Reagan to Chicago.

Which airlines fly direct from Washington Ronald Reagan to Chicago?

British Airways, American Airlines and Southwest Airlines fly direct from Washington Ronald Reagan to Chicago.

How many flights are there a week from Washington Ronald Reagan to Chicago?

As of January 2026, there are 660 flights per week flying from Washington Ronald Reagan to Chicago.

When is the cheapest time to fly from Washington Ronald Reagan to Chicago?

The cheapest month to fly from Washington Ronald Reagan to Chicago is usually April.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Washington Ronald Reagan Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $267.

Which upcoming date is cheapest to fly from Washington Ronald Reagan Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Washington Ronald Reagan Airport to Chicago on Thursday, 16 April 2026.

Can I get a direct flight from Washington Ronald Reagan Airport to Chicago?

Yes – the average flight time is 2 hours and 15 minutes.

How can I get the best flight deal from Washington Ronald Reagan Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In January, the average temperature is usually around -4°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Washington Ronald Reagan Airport to Chicago with?

Currently, Frontier Airlines and United offer the cheapest flight tickets to Chicago.

Travelling from Ronald Reagan National Airport (DCA) to Chicago: what you need to know

The average time for a direct flight from Ronald Reagan National Airport to Chicago is 1 hour 55 minutes.
Chicago is one hour behind Washington DC, where Ronald Reagan National Airport is located. Chicago follows the UTC-5 timezone.
Ronald Reagan National Airport (DCA) to O'Hare International Airport (ORD) is the most popular route, with 131 departures a week to pick from. If you prefer a later start to the day, the last flight from DCA to ORD is with American Airlines at 22:09. Choose the first departure with American Airlines at 05:59 if you want to fly out earlier.
For a smooth journey, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This leaves you with plenty of time to board your DCA to Chicago flight.
If you're heading away during a bank holiday or another peak period, give yourself more time. A good rule is two hours ahead of domestic flights and up to four hours before international departures. Check-in and security lines will be longer.
Begin your trip at DCA and fly nonstop to O'Hare International Airport (ORD). That will be your arrival point when searching for Ronald Reagan National Airport to Chicago tickets.
Well-known carriers that offer direct flights from Ronald Reagan National Airport to Chicago include:
DCA is around 6 kilometres from central Washington DC. If you're catching a cab, ride-sharing or driving from the centre, it'll take 15 minutes or so to get there, depending on traffic. If you're using public transport, expect the trip time to be around 45 minutes.
Want a relaxed start to your journey? Stay near DCA. Whether you're catching an early flight from Ronald Reagan National Airport to Chicago or don't want departure day to feel hectic, these hotels have you covered:
When it comes to Ronald Reagan National Airport's on-time performance, 76.44% of flights stick to their scheduled arrival time.
You'll find DCA at 1 Aviation Circle.

How to find the cheapest flights from Ronald Reagan National Airport (DCA) to Chicago

$123 is currently the lowest price for a one-way Ronald Reagan National Airport to Chicago flight. Return flight tickets start from $267. These prices may change based on availability.
Book one month before you want to fly. Pricing trends suggest that this is the ideal window for finding cheap flights from DCA to Chicago.
The best month for finding cheap Ronald Reagan National Airport to Chicago tickets is May. Use the 'Whole month' tool to compare prices, then choose the dates offering the lowest fares.
Locking in a cheap flight from DCA to Chicago is a breeze with Price Alerts. Simply set up one of these automatic notifications and we'll get in touch when a cheaper option becomes available.
Select your ideal arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Ronald Reagan National Airport to Chicago by 'Fastest,' 'Best' or 'Cheapest.'

Airports in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're opting for a ride-share or a cab, the drive will take roughly 35 minutes.
If you're travelling by public transport, expect a journey time of around 55 minutes.
The last thing you want is a long journey to your hotel if you're getting in late on a flight from Ronald Reagan National Airport to Chicago. Check in to one of these accommodation options near ORD instead:
Travel at your own speed with an O'Hare International Airport rental car. Pick up your wheels from Routes Car Rentals, Dollar or Budget and chase adventure across Chicago and beyond.
To get the lowest price, reserve your vehicle from O'Hare International Airport around four weeks ahead of your flight from DCA to Chicago.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

After your flight from Ronald Reagan National Airport to Chicago has hit the runway, you can make your way to the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).
You can expect the journey to take roughly 45 minutes on public transport.
Hang the 'Do not disturb' sign on your door and relax at a hotel near MDW. Here are a few options where you can tuck yourself in after your DCA to Chicago flight:
The quickest way to reach your destination is with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and make a speedy getaway.
Snap up a deal by reserving your ride from MDW four weeks in advance. You'll also have access to a greater range of vehicles.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Make your way to the city centre after your flight from Ronald Reagan National Airport to Chicago has touched down. Central Chicago is about 137 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by cab or ride-share.
Public transport can get you there in roughly 4 hours 15 minutes.
Book a hotel close to RFD and get from baggage claim to bedtime in a flash. Whether you're coming in on a late DCA to Chicago flight or just want an easier arrival, these accommodation options will have you settling in quickly:
Whether you want a mini for solo travel or a spacious SUV to fit the family, you'll find the ideal Chicago Rockford International Airport rental car for you. Check out the range of wheels available here from companies such as Budget, Alamo and National.
Booking at least a few weeks in advance of your flight from Ronald Reagan National Airport to Chicago is a good move. As well as better prices, you'll likely have a better variety of makes and models to choose from at RFD.
Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

Travel to Chicago in peak season if you like a busy atmosphere, but remember that hotel prices are typically higher. Alternatively, book your flights from Ronald Reagan National Airport to Chicago in the off-season when prices are cheaper and it's not as busy.
Book a Ronald Reagan National Airport to Chicago flight ticket with a departure in July if you're eager to experience the city during its warmest month. Expect temperatures to range from 15ºC to 29ºC.
If you'd rather travel in cooler conditions, search for a cheap ticket from DCA to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

When it comes to looking for somewhere to lay your head, you'll find the top stays in Chicago right here. Check out these hotels as soon as you've booked your flight from Ronald Reagan National Airport to Chicago:
Art Institute of Chicago and Millennium Park are just the start of the leading attractions to add to your Chicago travel itinerary. Continue your sightseeing adventures at LandShark Beer Garden at Navy Pier.

Explore more of United States

Chicago has plenty to offer, but there are so many other corners of United States you should also see. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep you busy. Start with leading sights like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without experiencing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.