S$ 65 Cheap Flights from Washington D.C. to Chicago (WAS-CHI)

App

Help

SGD

Search Bookings

Cheap Flights from Washington D.C. to Chicago

Hotels in Chicago

Worldwide Coverage

Flights to over 5,000 cities

One-stop Service Guarantee

Price guaranteed upon confirmed payment, booking guaranteed once tickets issued

Secure Payment

Convenient & reliable booking and payment system

Cheap Flights from Washington D.C. to Chicago starting at S$ 65

Book one-way or return flights from Washington D.C. to Chicago from as little as S$ 65. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Washington D.C. to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Washington D.C. to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Cheapest Airlines flying from Washington D.C. to Chicago

View airlines operating flights from Washington D.C. to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines

From S$ 65

Southwest Airlines

From S$ 102

Delta Air Lines

From S$ 105

Sun Country Airlines

From S$ 110

United Airlines

From S$ 112

Jetblue Airways

From S$ 130

Frontier Airlines

From S$ 543

ANA airlines

Find more flights and airlines

Alternative Routes from Washington D.C. to Chicago

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Washington D.C. to Chicago.

Cheapest
DCA
06:48
2h 11m
Direct
ORD
07:59
Ronald Reagan Washington National Airport - O'Hare International Airport
Tue, May 28American Airlines
S$ 65
DCA
06:25
2h 0m
Direct
MDW
07:25
Ronald Reagan Washington National Airport - Midway International Airport
Tue, May 14Southwest Airlines
S$ 102
IAD
09:40
3h 57m
1 transfer
ORD
12:37
Dulles International Airport - O'Hare International Airport
Tue, May 14Delta Air Lines
S$ 107
IAD
09:40
3h 57m
1 transfer
ORD
12:37
Dulles International Airport - O'Hare International Airport
Tue, May 14Delta Air Lines
S$ 107
Find More Flights

Frequently Asked Questions

When to buy flight tickets from Washington D.C. (WAS) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Washington D.C. to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much is a flight from Washington D.C. (WAS) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around S$ 370.
How long is a flight from Washington D.C. (WAS) to Chicago (CHI)?
It takes about 2 hours 12 minutes to fly from Washington D.C. (WAS) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What time does the earliest flight from Washington D.C. to Chicago depart?
The earliest flight departs from Washington D.C. (DCA) at 06:00 and arrives in Chicago (ORD) at 07:11.
What time does the latest flight from Washington D.C. to Chicago depart?
The latest flight departs from Washington D.C. (DCA) at 20:00 and arrives in Chicago (ORD) at 21:13.
What are the most popular airlines that fly from Washington D.C. (WAS) to Chicago (CHI)?
Airlines with flights from Washington D.C. (WAS) to Chicago (CHI): Qatar Airways, American Airlines, United Airlines, Air New Zealand, Ana, Alaska Airlines, Royal Jordanian, Austrian Airlines and Japan Airlines.
What's the most popular airline for direct flights from Washington D.C. (WAS) to Chicago (CHI)?
Southwest Airlines operates 7 direct flights from Washington D.C. (WAS) to Chicago (CHI).
How many airports in Chicago?
There are 5 airports near Chicago: O'Hare International Airport, Chicago Du Page County Airport, Midway International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from Washington D.C. to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Washington D.C. to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information from Washington D.C. to Chicago

Cheapest direct flight price	S$ 64
Cheapest return ticket price	S$ 145
Cheapest month	April
Peak season for travel	August
Flight distance	957.18km
Average flight time	2 hours 12 minutes
Popular airline	Delta Air Lines