C$121 Cheap Flights from Washington Ronald Reagan (DCA) to Chicago (CHIA)

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Flight deals from Washington Ronald Reagan 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 C$271. Find the lowest prices on one-way and return tickets right here.

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 September.

Which airlines fly 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 foundC$121
Cheapest month to flySeptember
Average flight time2 hrs, 14 mins
Most popular airlineAmerican Airlines
Average flights per week541

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Washington Ronald Reagan to Chicago is C$243. 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.
2 hours and 14 minutes is the average flight time from Washington Ronald Reagan to Chicago.
American Airlines, Southwest Airlines and British Airways fly direct from Washington Ronald Reagan to Chicago.
As of June 2026, there are 541 flights per week flying from Washington Ronald Reagan to Chicago.
The cheapest month to fly from Washington Ronald Reagan to Chicago is usually August.
If you're flying from Washington Ronald Reagan Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from C$243.
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 Tuesday, August 18, 2026.
Yes – the average flight time is 2 hours and 14 minutes.
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.
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.
In June, the average temperature is usually around 19°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.
Currently, Delta and Southwest Airlines offer the cheapest flight tickets to Chicago.

Flying 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 53 minutes.

  • The timezone in Chicago is UTC-5. The city is 1 hour behind Washington DC, where Ronald Reagan National Airport is located.

  • With 168 flights a week between the two airports, Ronald Reagan National Airport (DCA) to O'Hare International Airport (ORD) is the busiest route. American Airlines operates the earliest flight at 05:59. If you'd like to get more out of your day before leaving, the latest flight from DCA to ORD is with United at 20:40.

  • To ensure you get on your flight from DCA to Chicago, leave plenty of time to navigate the airport and find your gate. Arriving two hours ahead of international departures and an hour before domestic flights is the general rule.

  • If you're flying during a peak month like July, head to the airport even earlier. It's wise to arrive up to four hours before an international flight and two hours ahead of domestic departures. Security lines will be longer during high seasons like summer and spring break.

  • You can book a direct flight from Ronald Reagan National Airport to Chicago that lands at O'Hare International Airport (ORD).

  • Pick from a variety of airlines that operate direct flights from Ronald Reagan National Airport to Chicago. Head off on your trip with any of these:

  • You don't need your passport or a visa to travel within United States. You will need a valid identity document though, like a driver's licence or an ID card. Make sure they're on your packing list once you've booked your flight tickets from Ronald Reagan National Airport to Chicago.

  • Travelling from central Washington DC to DCA takes about 43 minutes by public transport. If you drive, ride-share or take a cab, you'll cover the 8 kilometres in 16 minutes or so, depending on traffic conditions.

  • Want a relaxed start to your travels? Stay near DCA. Whether you're boarding an early flight from Ronald Reagan National Airport to Chicago or just don't like being rushed, these hotels are perfect:

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

  • C$121 is the best price for a one-way ticket from Ronald Reagan National Airport to Chicago. Return flights start from C$243. These fares can change depending on demand and availability.

  • Book 9 months before you want to fly. After looking at the numbers on our calendar, this is how far you'll want to book ahead to secure cheap tickets from DCA to Chicago.

  • Plan your trip for May. That's the cheapest month for tickets from Ronald Reagan National Airport to Chicago. If you're flexible with your dates, use the 'Whole month' tool to find the cheapest price across every month.

  • Log into your online account or use the app to create a Price Alert. We'll notify you straight away if there's a cheaper deal on this route. It doesn't take long, and it'll save you from checking for cheap tickets from DCA to Chicago every day.

  • Play around with the filters to find your ideal trip. To see the 'Best,' 'Fastest' or 'Cheapest' flights from Ronald Reagan National Airport to Chicago, use the 'Sort by' tool. You can also filter by airline, departure and arrival times, and number of stops.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago is approximately 40 kilometres. It takes about 35 minutes to reach the centre driving.

  • Travelling to the centre on public transport will take you roughly 54 minutes.

  • If you're coming in on a late flight from Ronald Reagan National Airport to Chicago, few things beat the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and resting not long after at one of these accommodation options near ORD:

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the most popular month to catch a flight from Ronald Reagan National Airport to Chicago while February is the quietest. To work out the ideal time to go to Chicago, consider the pace you prefer to travel at.

  • When booking your flight from Ronald Reagan National Airport to Chicago, think about the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • Look for cheap flights from DCA to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the ideal place to stay. As soon as you've booked your flight from Ronald Reagan National Airport to Chicago, check out our selection of accommodation options including:

  • There are so many things to discover in this city it can be hard to work out where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are top attractions which should feature on any good Chicago itinerary.

Complete your Chicago trip with a car rental

  • Select one of our car rentals in Chicago and explore the city on your own terms. Easily compare options in one place to find the perfect ride once you've locked in your hotel and cheap flights from Ronald Reagan National Airport to Chicago.

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.