Cheap Flights Washington D.C. – Chicago from CAD 120

Flight FAQs

• Which airlines offer the cheapest flights from Washington D.C. (WAS) to Chicago (CHI)?

  Based on Trip.com data, Frontier Airlines offers one-way fares as low as CAD 120 on Cheapest nonstop routes (e.g. IAD to MDW on Mon, May 25), while Frontier Airlines offers Cheapest nonstop round-trips from CAD 196 departing on Sat, May 16 and returning on Tue, May 19.

• Which airlines offer direct flights from Washington D.C. to Chicago?

  At the moment, you can catch a direct flight from Washington D.C. to Chicago with the following airlines, including: American Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

• How long is the flight from Washington D.C. (WAS) to Chicago (CHI)?

  It takes about 2 hours 14 minutes to fly from Washington D.C. (WAS) to Chicago (CHI).

• When is the best time to book flights from Washington D.C. to Chicago?

  By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Washington D.C. to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

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

  Based on Trip.com data in the past 4 weeks, there is 194 flight per week flying from Washington D.C. to Chicago. You can check the weekly schedule for popular airlines on this route below: American Airlines: S/M/T/W/T/F/S -- AA2903 (23:02)

• How can I find the best deals on flights from Washington D.C. to Chicago?

  To find best deals on flights from Washington D.C. to Chicago, you can use various tools on Trip.com:
  · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Mon, May 25, with one-way flights priced at just CAD 120.
  · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
  · Set up price alerts to easily monitor ticket prices without having to check every day.
  · Check Trip.com flight deals and promo codes frequently.
  · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
  · Get exclusive promo codes for Trip.com app users.

• When is the best time to book a flight from Washington D.C. to Chicago to get the best price?

  The cheapest months to fly from Washington D.C. to Chicago is November, when demand for travel is lower.

• Which upcoming date is the cheapest for flights from Washington D.C. to Chicago?

  After crunching the numbers on our May flight calendar, it's currently cheapest to fly from Washington D.C. to Chicago on May 19, 2026 with Frontier Airlines, with prices starting at CAD 68.

• Which airports can I fly through when travelling to Chicago from Washington D.C.?

  You can land at any one of the following hubs in Chicago, with Dulles International Airport to Chicago O'Hare International Airport (IAD-ORD) is by far the most common option on this route: Chicago Midway International Airport (MDW) Chicago O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).

• What is the time difference between Washington D.C. and Chicago?

  The time difference between Chicago and Washington D.C. is 1h.

• How can I change or cancel my flight ticket from Washington D.C. to Chicago?

  Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.