Cheap Flights from Washington D.C. to Chicago

Compare Washington D.C. to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from Washington D.C. to Chicago

Looking for a cheap last-minute deal or the best return flight from Washington D.C. to Chicago? If you want to travel next month, return fares start from $258. Find the lowest prices on one-way and return tickets right here.

Chicago.$228 per passenger.Departing Mon, 11 May, returning Thu, 14 May.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Mon, 11 May, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Thu, 14 May, arriving in Baltimore Washington International.Price includes taxes and charges.From $228, select.

Chicago.$258 per passenger.Departing Mon, 13 Apr, returning Thu, 16 Apr.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Mon, 13 Apr, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Thu, 16 Apr, arriving in Baltimore Washington International.Price includes taxes and charges.From $258, select.

Chicago.$272 per passenger.Departing Fri, 24 Apr, returning Fri, 1 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Fri, 24 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 1 May, arriving in Baltimore Washington International.Price includes taxes and charges.From $272, select.

Chicago.$278 per passenger.Departing Wed, 18 Mar, returning Tue, 31 Mar.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Baltimore Washington International on Wed, 18 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 31 Mar, arriving in Baltimore Washington International.Price includes taxes and charges.From $278, select.

Chicago.$282 per passenger.Departing Wed, 18 Mar, returning Wed, 1 Apr.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Baltimore Washington International on Wed, 18 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Wed, 1 Apr, arriving in Baltimore Washington International.Price includes taxes and charges.From $282, select.

Chicago.$306 per passenger.Departing Mon, 1 Jun, returning Fri, 5 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Baltimore Washington International on Mon, 1 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 5 Jun, arriving in Baltimore Washington International.Price includes taxes and charges.From $306, select.

Chicago.$306 per passenger.Departing Sun, 31 May, returning Thu, 4 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Baltimore Washington International on Sun, 31 May, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 4 Jun, arriving in Baltimore Washington International.Price includes taxes and charges.From $306, select.

Chicago.$353 per passenger.Departing Wed, 29 Apr, returning Tue, 5 May.Return flight with United.Outbound direct flight with United departs from Baltimore Washington International on Wed, 29 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 5 May, arriving in Baltimore Washington International.Price includes taxes and charges.From $353, select.

Chicago.$355 per passenger.Departing Tue, 31 Mar, returning Tue, 7 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Tue, 31 Mar, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 7 Apr, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $355, select.

Chicago.$385 per passenger.Departing Thu, 4 Jun, returning Tue, 9 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Thu, 4 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 9 Jun, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $385, select.

Chicago.$410 per passenger.Departing Mon, 4 May, returning Mon, 1 Jun.Return flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Mon, 4 May, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 1 Jun, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $410, select.

Chicago.$428 per passenger.Departing Mon, 23 Mar, returning Mon, 30 Mar.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Mon, 23 Mar, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 30 Mar, arriving in Baltimore Washington International.Price includes taxes and charges.From $428, select.

Chicago.$457 per passenger.Departing Sat, 27 Jun, returning Thu, 2 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Sat, 27 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 2 Jul, arriving in Baltimore Washington International.Price includes taxes and charges.From $457, select.

Chicago.$457 per passenger.Departing Thu, 9 Jul, returning Thu, 16 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Thu, 9 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 16 Jul, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $457, select.

Chicago.$461 per passenger.Departing Thu, 3 Sep, returning Mon, 7 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Baltimore Washington International on Thu, 3 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 7 Sep, arriving in Baltimore Washington International.Price includes taxes and charges.From $461, select.

Chicago.$474 per passenger.Departing Sat, 29 Aug, returning Thu, 3 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 29 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 3 Sep, arriving in Washington Ronald Reagan.Price includes taxes and charges.From $474, select.

Find the cheapest month to fly from Washington D.C. to Chicago

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

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Direct flights from Washington D.C. to Chicago

Alternative Washington D.C. to Chicago routes

Looking for the cheapest, fastest or easiest route from Washington D.C. 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	$228
Cheapest month to fly	May
Average flight time	2 hrs, 14 mins
Most popular airline	American Airlines
Average flights per week	1,017

Finding cheap flights from Washington D.C. 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 D.C. to Chicago?

The best price we found for a return flight from Washington D.C. to Chicago is $228. 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 D.C. to Chicago?

2 hours and 14 minutes is the average flight time from Washington D.C. to Chicago.

Which airlines fly direct from Washington D.C. to Chicago?

American Airlines, United and Southwest Airlines fly direct from Washington D.C. to Chicago.

How many flights are there a week from Washington D.C. to Chicago?

As of March 2026, there are 1,017 flights per week flying from Washington D.C. to Chicago.

When is the cheapest time to fly from Washington D.C. to Chicago?

The cheapest month to fly from Washington D.C. to Chicago is usually May.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Washington D.C., 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 $228.

Which upcoming date is cheapest to fly from Washington D.C. to Chicago on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Washington D.C. to Chicago on Monday, 11 May 2026.

Can I get a direct flight from Washington D.C. to Chicago?

Yes – the average flight time is 2 hours and 14 minutes.

How can I get the best flight deal from Washington D.C. 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 March, the average temperature is usually around 3°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 D.C. to Chicago with?

The cheapest airline that flies to Chicago is Frontier Airlines .

Flying from Washington DC to Chicago: what you need to know

Start planning your trip by checking out the ideal departure point for your flight from Washington DC to Chicago. Explore your options for setting off from Ronald Reagan National Airport (DCA) or Washington Dulles International Airport (IAD), two of the city's main airports.
The major entry paths to Chicago are O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW).
The average time for a direct Washington DC to Chicago flight is 2 hours 10 minutes.
Chicago's timezone is UTC-5, which makes Chicago one hour behind Washington DC.
With 131 flights a week between the two airports, Ronald Reagan National Airport (DCA) to O'Hare International Airport (ORD) is the busiest route. Hop on the first flight from Washington DC to Chicago with American Airlines at 05:59. If you prefer to make the most of your day before taking off, the latest flight from DCA to ORD is with American Airlines at 22:09.
Allow plenty of time to catch your Washington DC to Chicago flight. As a rule of thumb, arrive at least two hours before international departures and an hour ahead for domestic flights.
During popular months like July, it's best to get to the airport earlier. Plan to arrive two hours before a domestic departure and four hours ahead of international flights whenever you're travelling during high season in general.

How to find the cheapest flights from Washington DC to Chicago

Currently, $103 is the best price we've seen for a one-way ticket from Washington DC to Chicago. The cheapest price for a return flight is $228. Keep in mind fares can change due to demand at the time of booking.
To secure cheap Washington DC to Chicago flights, reserve your trip two months before your planned departure.
Organise your trip for May. That's the best month for landing an incredible deal on plane tickets from Washington DC to Chicago. If you're open to different travel dates, use the 'Whole month' tool to find the cheapest price across every month.
Finding a cheap flight from Washington DC to Chicago is easy with Price Alerts. Simply set up one of these automatic alerts and we'll let you know when there's a better deal.
Tailor your travel plans using filters. Select your ideal arrival and departure times, total journey duration and airlines. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' Washington DC to Chicago flights.

Flying from Washington DC

Ronald Reagan National Airport (DCA)

You can book a direct flight from Washington DC to Chicago departing from Ronald Reagan National Airport (DCA). Board your plane at DCA and then hit the runway at O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).
Top airlines that offer direct Washington DC to Chicago plane tickets departing from DCA include:
Located around 6 kilometres from the centre of Washington DC, DCA can be reached in about 15 minutes by car (depending on traffic). The journey on public transport will take roughly 45 minutes.
Want a handy hotel near Ronald Reagan National Airport? If you're catching an early flight from Washington DC to Chicago, these accommodation options will have you moments from check-in:
When it comes to the on-time performance of Ronald Reagan National Airport, data shows 76.44% of flights arrive within the expected time frame.
The address for DCA is 1 Aviation Circle.

Washington Dulles International Airport (IAD)

You can take a direct flight from Washington DC to Chicago leaving from Washington Dulles International Airport (IAD). Start your trip at IAD and touch down at O'Hare International Airport (ORD).
United Airlines offers direct Washington DC to Chicago plane tickets from IAD. Book your favourite aisle (or window) seat and reach your destination in a single hop.
IAD is around 40 kilometres from central Washington DC. It'll take you 50 minutes or so to get to the airport driving from the city centre. Public transport takes roughly 1 hour 10 minutes.
Kick off your holiday early with an extra night away from home. Before your flight from Washington DC to Chicago, unwind in one of these hotels near Washington Dulles International Airport:
74% of flights leaving Washington Dulles International Airport stick to their scheduled arrival time.
You'll find IAD at 1 Saarinen Circle.

Baltimore/Wash International Thurgood Marshall Airport (BWI)

Baltimore/Wash International Thurgood Marshall Airport (BWI) offers direct flights from Washington DC to Chicago. You can fly straight to O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) without the hassle of layovers.
Numerous airlines offer direct Washington DC to Chicago plane tickets from BWI. Jet off with one of these popular carriers:
The journey time to BWI from the centre of Washington DC is around 1 hour 30 minutes by public transport. If you prefer to travel by car, it'll take you about 50 minutes to cover the 40 kilometres or so.
Wake up, take it easy and still make your Washington DC to Chicago flight with plenty of time to spare. These accommodation options near Baltimore/Wash International Thurgood Marshall Airport make departure day effortless if you're flying out early:
The on-time performance record of BWI is 77.13%. To put it simply, that's how frequently flights that depart this airport arrive at their destination as planned.

Arriving in Chicago

O'Hare International Airport (ORD)

The distance from O'Hare International Airport (ORD) to central Chicago is approximately 26 kilometres. It'll take you about 35 minutes to get to the centre driving.
It usually takes 55 minutes to get there on public transport.
Reserve a hotel near ORD if you're coming in on a late flight from Washington DC to Chicago. Choose one of these accommodation options and avoid the hassle of a long transfer:
Grab an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are popular outlets you can book with here.
For the lowest price, book your ride from O'Hare International Airport about four weeks in advance of your Washington DC to Chicago flight.
The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) is around 14 kilometres from central Chicago. After your flight from Washington DC to Chicago, it'll take you approximately 20 minutes to reach the heart of the city in a ride-share or cab.
If you hop on public transport, the ride to the centre will take you 45 minutes or so.
Place the 'Do not disturb' sign on your door and relax at a hotel close to MDW. Here are a few options where you can settle in after your flight from Washington DC to Chicago:
Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car simple. These providers are located around or in the terminal and will have you on the road before long.
Score the best price by booking your ride from MDW four weeks ahead of time. You can also expect to have a bigger selection of vehicles.
You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Head to the city centre after your flight from Washington DC to Chicago has landed. Central Chicago is about 129 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to reach by car.
Public transport will take you there in roughly 4 hours 15 minutes.
Whether you'd like a zippy mini for a solo trip or a roomy SUV to move the whole family, you'll find the right Chicago Rockford International Airport rental car for your needs. Explore the types of wheels available from providers such as Budget, Alamo and National.
Rental agencies sometimes offer deals on early bookings, so book your ride from RFD ahead of your flight from Washington DC to Chicago. A little prep today saves cash tomorrow.
The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from Washington DC to Chicago, while August is the busiest. Figure out the best time to go to Chicago based on whether you want a lively atmosphere or a more laid-back vibe.
Lock in a Washington DC to Chicago ticket departing in July if you want to explore the city during its warmest month. You can expect temperatures in Chicago to range from 15ºC to 29ºC.
January sees average temperatures of between -12ºC and 3ºC. Look for cheap flights from Washington DC to Chicago around that time if you want to travel when it's cooler.

More about Chicago

When it comes to looking for somewhere to lay your head, you'll find the best stays in Chicago right here. Explore these options after you've booked your flight from Washington DC to Chicago:
Millennium Park and Art Institute of Chicago are just two of the major attractions to put on your Chicago itinerary. Continue your sightseeing adventures at LandShark Beer Garden at Navy Pier.

Explore more of United States

Columbus is just one of the many places in United States waiting to be explored once you've seen the sights of Chicago. Around 451 kilometres to the south-east, top sights here include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Experience major highlights starting with The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.