Cheap flights from Washington Dulles to Chicago

Compare Washington Dulles to Chicago flight deals

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Flight deals from Washington Dulles to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Washington Dulles Airport to Chicago? If you want to travel next month, round-trip fares start from $157. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$158 per passenger.Departing Tue, Aug 18, returning Wed, Aug 26.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Washington Dulles on Tue, Aug 18, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Wed, Aug 26, arriving in Washington Dulles.Price includes taxes and charges.From $158, select.

Chicago.$170 per passenger.Departing Sat, Oct 3, returning Mon, Oct 5.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Washington Dulles on Sat, Oct 3, arriving in Chicago Rockford.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Mon, Oct 5, arriving in Washington Dulles.Price includes taxes and charges.From $170, select.

Chicago.$173 per passenger.Departing Sat, Aug 29, returning Tue, Sep 1.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Washington Dulles on Sat, Aug 29, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Tue, Sep 1, arriving in Washington Dulles.Price includes taxes and charges.From $173, select.

Chicago.$177 per passenger.Departing Tue, Aug 25, returning Wed, Sep 9.Round-trip flight with United.Outbound direct flight with United departing from Washington Dulles on Tue, Aug 25, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Wed, Sep 9, arriving in Washington Dulles.Price includes taxes and charges.From $177, select.

Chicago.$177 per passenger.Departing Tue, Aug 18, returning Wed, Aug 19.Round-trip flight with United.Outbound direct flight with United departing from Washington Dulles on Tue, Aug 18, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Wed, Aug 19, arriving in Washington Dulles.Price includes taxes and charges.From $177, select.

Chicago.$177 per passenger.Departing Tue, Nov 3, returning Tue, Nov 10.Round-trip flight with United.Outbound direct flight with United departing from Washington Dulles on Tue, Nov 3, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Tue, Nov 10, arriving in Washington Dulles.Price includes taxes and charges.From $177, select.

Chicago.$177 per passenger.Departing Sat, Oct 17, returning Wed, Oct 21.Round-trip flight with United.Outbound direct flight with United departing from Washington Dulles on Sat, Oct 17, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Wed, Oct 21, arriving in Washington Dulles.Price includes taxes and charges.From $177, select.

Chicago.$177 per passenger.Departing Wed, Sep 16, returning Wed, Sep 23.Round-trip flight with United.Outbound direct flight with United departing from Washington Dulles on Wed, Sep 16, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Wed, Sep 23, arriving in Washington Dulles.Price includes taxes and charges.From $177, select.

Chicago.$185 per passenger.Departing Wed, Sep 30, returning Mon, Oct 5.Round-trip flight with United.Outbound direct flight with United departing from Washington Dulles on Wed, Sep 30, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Mon, Oct 5, arriving in Washington Dulles.Price includes taxes and charges.From $185, select.

Chicago.$195 per passenger.Departing Wed, Jul 29, returning Tue, Aug 4.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Washington Dulles on Wed, Jul 29, arriving in Chicago Rockford.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Tue, Aug 4, arriving in Washington Dulles.Price includes taxes and charges.From $195, select.

Chicago.$196 per passenger.Departing Wed, Jul 22, returning Wed, Jul 29.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Washington Dulles on Wed, Jul 22, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Wed, Jul 29, arriving in Washington Dulles.Price includes taxes and charges.From $196, select.

Chicago.$196 per passenger.Departing Tue, Dec 1, returning Tue, Dec 8.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Washington Dulles on Tue, Dec 1, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Tue, Dec 8, arriving in Washington Dulles.Price includes taxes and charges.From $196, select.

Chicago.$197 per passenger.Departing Wed, Oct 21, returning Tue, Nov 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Washington Dulles on Wed, Oct 21, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Tue, Nov 3, arriving in Washington Dulles.Price includes taxes and charges.From $197, select.

Chicago.$211 per passenger.Departing Wed, Dec 9, returning Thu, Dec 10.Round-trip flight with United.Outbound direct flight with United departing from Washington Dulles on Wed, Dec 9, arriving in Chicago O'Hare International.Inbound direct flight with United departing from Chicago O'Hare International on Thu, Dec 10, arriving in Washington Dulles.Price includes taxes and charges.From $211, select.

Chicago.$235 per passenger.Departing Sat, Jul 25, returning Sat, Oct 10.Round-trip flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departing from Washington Dulles on Sat, Jul 25, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Sat, Oct 10, arriving in Washington Dulles.Price includes taxes and charges.From $235, select.

Chicago.$258 per passenger.Departing Sat, Nov 28, returning Thu, Dec 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Washington Dulles on Sat, Nov 28, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Thu, Dec 3, arriving in Washington Dulles.Price includes taxes and charges.From $258, select.

Find the cheapest month to fly from Washington Dulles to Chicago

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

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Direct flights from Washington Dulles to Chicago

Alternative Washington Dulles to Chicago routes

Looking for the cheapest, fastest or easiest route from Washington Dulles 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	$157
Cheapest month to fly	August
Average flight time	2 hrs, 18 mins
Most popular airline	United
Average flights per week	236

Finding cheap flights from Washington Dulles to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are round-trip flights from Washington Dulles to Chicago?

The best price we found for a round-trip flight from Washington Dulles to Chicago is $157. 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 Dulles to Chicago?

2 hours and 18 minutes is the average flight time from Washington Dulles to Chicago.

Which airlines fly direct from Washington Dulles to Chicago?

United, Air Canada and Air New Zealand fly direct from Washington Dulles to Chicago.

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

There are 236 flights per week flying from Washington Dulles to Chicago, as of July 2026.

When is the cheapest time to fly from Washington Dulles to Chicago?

The cheapest month to fly from Washington Dulles to Chicago is usually August.

What's the cheapest airport to fly to in Chicago?

If you're flying from Washington Dulles Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the center of Chicago. We've found flights to this airport from $157.

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Washington Dulles Airport to Chicago on Tuesday, August 18, 2026.

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

Yes – the average flight time is 2 hours and 18 minutes.

How can I get the best flight deal from Washington Dulles 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 July, the average temperature is usually around 22°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 with from Washington Dulles Airport to Chicago?

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

Flying from Washington Dulles International Airport (IAD) to Chicago: what you need to know

Book a direct flight from Washington Dulles International Airport to Chicago and you'll be traveling for an average of 1 hour 55 minutes.
Chicago is one hour behind Washington DC, where Washington Dulles International Airport is located. Chicago observes the UTC-6 timezone.
With 38 flights a week between the two airports, Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD) is the most popular route. United Airlines operates the earliest flight at 06:10. If you'd like to get more out of your day before jetting off, the latest departure from IAD to ORD is with United Airlines at 22:20.
To avoid missing your IAD to Chicago flight, leave plenty of time to check in and find your gate. Arriving two hours before international departures and one hour before domestic flights is the general travel rule.
During popular months such as June, it's a good idea to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead of an international flight when you fly during peak periods in general.
Direct Washington Dulles International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll complete your journey.
Book your favorite seat with United Airlines. This popular airline operates direct flights from Washington Dulles International Airport to Chicago.
Located around 40 kilometers from the center of Washington DC, IAD can be reached in about 45 minutes by car. The journey on public transport takes roughly 1 hour 10 minutes.
Searching for a hotel near IAD? If you're catching an early flight from Washington Dulles International Airport to Chicago, these accommodation options will put you moments from your departure lounge:
When it comes to the on-time performance of Washington Dulles International Airport, 77% of flights stick to their scheduled arrival time.
IAD is located at 1 Saarinen Circle.

How to find the cheapest flights from Washington Dulles International Airport (IAD) to Chicago

$77 is the cheapest price we've seen for a one-way Washington Dulles International Airport to Chicago flight. A return plane ticket right now is $157. Depending on when you book and the availability, these fares may change.
Book five months before your departure date. Pricing trends suggest that this is the ideal window for finding cheap flights from IAD to Chicago.
October is the best month for picking up an incredible deal on Washington Dulles International Airport to Chicago tickets. If you want to travel during a different time of year, the 'Whole month' tool will show you the lowest prices for each month.
There's no need to check back in every day to find out if fares have dropped when you set up a Price Alert. We'll let you know the moment there's an even bigger deal on cheap flights from IAD to Chicago.
Snag an affordable flight from Washington Dulles International Airport to Chicago with the help of our filters. Choose your ideal duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometers. It takes about 30 minutes to reach the center driving.
Getting there on public transport takes around 45 minutes.
The last thing you want is a long journey to your hotel if you're getting in late on a flight from Washington Dulles International Airport to Chicago. Reserve one of these accommodation options near ORD instead:
Lock in the best deal by reserving your ride from Chicago O'Hare International Airport around four weeks in advance of your flight from IAD to Chicago.
The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Once your flight from Washington Dulles International Airport to Chicago has hit the tarmac, you can reach the city center in about 25 minutes by car. Central Chicago is roughly 16 kilometers from Chicago Midway International Airport (MDW).
If you travel by public transport, the journey will take you 30 minutes or so.
You'll find some comfortable places ready to welcome you near MDW. Settle in and get cozy after your IAD to Chicago flight at any of these perfectly located options:
Snap up a deal by booking your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.
Chicago Midway International Airport is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Make tracks for the city center after your flight from Washington Dulles International Airport to Chicago has landed. Central Chicago is around 145 kilometers from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to reach by car.
If you're using public transport, expect a journey of around 2 hours.
Stay at a hotel close to RFD and go from landing to lounging in your room in a flash. Whether you have a late IAD to Chicago flight or just want to keep your travel plans simple, these accommodation options are all about convenience:
Booking a couple of weeks in advance of your flight from Washington Dulles International Airport to Chicago is a smart way to go. As well as better deals, you'll get a better selection of vehicle makes and models at RFD.
Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

July is the most popular month for flights from Washington Dulles International Airport to Chicago. To avoid the crowds, visit Chicago in January.
Lock in a Washington Dulles International Airport to Chicago plane ticket with a departure in July if you're eager to experience the city during its warmest month. Expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).
For cooler conditions, look for a cheap ticket from IAD to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Start your Chicago trip off on the right foot by choosing the perfect place to stay. As soon as you've booked your flight from Washington Dulles International Airport to Chicago, explore our selection of hotels including:
Art Institute of Chicago and Millennium Park are just two of the leading attractions to add to your Chicago must-do list. Continue your sightseeing adventures at Willis Tower.

Explore more of the United States

Chicago has plenty going for it, but there are so many other corners of the United States you should also see. Around 451 kilometers southeast of Chicago, a visit to Columbus will fill your itinerary to the brim. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theater.
If you're ready to explore another great destination in the United States, head for Indianapolis, roughly 257 kilometers southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are key reasons to visit.