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C$87 Cheap Flights from Washington D.C. (WASA) to Chicago (CHIA)

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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 C$178. Find the lowest prices on one-way and return tickets right here.
Chicago.C$87 per passenger.Departing Tue., Jun. 30.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Tue., Jun. 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$87, select.
Chicago.C$87 per passenger.Departing Tue., Aug. 11.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Baltimore Washington International on Tue., Aug. 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$87, select.
Chicago.C$90 per passenger.Departing Wed., May 27.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Wed., May 27, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$90, select.
Chicago.C$94 per passenger.Departing Sat., Jul. 4.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Baltimore Washington International on Sat., Jul. 4, arriving in Chicago Midway.Price includes taxes and charges.From C$94, select.
Chicago.C$120 per passenger.Departing Wed., Jul. 1.One-way flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Wed., Jul. 1, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$120, select.
Chicago.C$120 per passenger.Departing Wed., May 27.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Wed., May 27, arriving in Chicago Midway.Price includes taxes and charges.From C$120, select.
Chicago.C$120 per passenger.Departing Tue., Jun. 2.One-way flight with United.Outbound direct flight with United departs from Baltimore Washington International on Tue., Jun. 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$120, select.
Chicago.C$120 per passenger.Departing Tue., Sep. 15.One-way flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Tue., Sep. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$120, select.
Chicago.C$120 per passenger.Departing Tue., Aug. 11.One-way flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Tue., Aug. 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$120, select.
Chicago.C$150 per passenger.Departing Thu., Oct. 1.One-way flight with Allegiant Air.Outbound indirect flight with Allegiant Air, departs from Washington Dulles on Thu., Oct. 1, arriving in Chicago Rockford.Price includes taxes and charges.From C$150, select.
Chicago.C$172 per passenger.Departing Fri., Oct. 16.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Fri., Oct. 16, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$172, select.
Chicago.C$194 per passenger.Departing Sat., Dec. 12.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Sat., Dec. 12, arriving in Chicago Midway.Price includes taxes and charges.From C$194, select.
Chicago.C$195 per passenger.Departing Mon., Nov. 30.One-way flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Mon., Nov. 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$195, select.
Chicago.C$196 per passenger.Departing Sat., Jan. 2.One-way flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Sat., Jan. 2, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$196, select.
Chicago.C$209 per passenger.Departing Sat., Feb. 13.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Ronald Reagan on Sat., Feb. 13, arriving in Chicago Midway.Price includes taxes and charges.From C$209, select.
Chicago.C$210 per passenger.Departing Mon., Mar. 15.One-way flight with United.Outbound direct flight with United departs from Baltimore Washington International on Mon., Mar. 15, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$210, 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 June.
May
from C$90
Jun.
from C$87
Jul.
from C$94
Aug.
from C$87
Sep.
from C$120
Oct.
from C$150
Nov.
from C$195
Dec.
from C$194
Jan.
from C$196
Feb.
from C$209
Mar.
from C$210
Apr.
Find prices

Which airlines fly 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.

Chicago Midway

14km from central Chicago
Closest
from C$88
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from C$87
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from C$102
Search flights

Washington D.C. to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$87
Cheapest month to flyJune
Average flight time2 hrs, 14 mins
Most popular airlineAmerican Airlines
Average flights per week1,089

Finding cheap flights from Washington D.C. 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 D.C. to Chicago is C$178. 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 13 minutes is the average flight time from Washington D.C. to Chicago.
American Airlines, Southwest Airlines and United fly direct from Washington D.C. to Chicago.
As of May 2026, there are 8,820 flights per week flying from Washington D.C. to Chicago.
The cheapest month to fly from Washington D.C. to Chicago is usually June.
If you're flying from Washington D.C., 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$178.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Washington D.C. to Chicago on Tuesday, June 2, 2026.
Yes – the average flight time is 2 hours and 13 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 May, the average temperature is usually around 13°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.
The cheapest airline that flies to Chicago is Frontier Airlines. And the cheapest airline that flies to Chicago O'Hare International Airport is Southwest Airlines.

Travelling 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 the options for taking off from Ronald Reagan National Airport (DCA) or Washington Dulles International Airport (IAD), two of the city's main airports.

  • O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the major arrival points in Chicago.

  • The average duration of a direct flight from Washington DC to Chicago is 2 hours 8 minutes. Chicago's timezone is UTC-5, making Chicago 1 hour behind Washington DC.

  • With 168 flights a week between the two airports, Ronald Reagan National Airport (DCA) to O'Hare International Airport (ORD) is the most popular route. Board the earliest 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 departure from DCA to ORD is with United Airlines at 20:40.

  • For a stress-free journey, turn up at the airport two hours ahead of international flights and an hour before domestic departures. This will give you plenty of time to board your flight from Washington DC to Chicago.

  • Delays at security and check-in are likely if you're jetting off during high season, so allow even more breathing space. A good rule for peak periods? Arrive up to four hours early for international flights and two hours for domestic departures.

  • Once you've found cheap flights from Washington DC to Chicago, get your documents in order. A passport or visa isn't required since you're travelling within United States. As long as you have some other valid form of identification, such as an ID card or driver's licence, you're good to go.

Flying from Washington DC

Ronald Reagan National Airport (DCA)

  • You can book a direct flight from Washington DC to Chicago taking off from Ronald Reagan National Airport (DCA). Start your journey at DCA and touch down at O'Hare International Airport (ORD).

  • When jetting out of DCA, you can catch a direct flight from Washington DC to Chicago with United Airlines.

  • We make it a cinch to book a flight from Washington DC to Chicago with a stopover. To see your options leaving from Ronald Reagan National Airport, deselect 'Direct flights only.' Next, select a flight that has a stop long enough to tour your chosen city. Some popular stopovers include:

    • Sarasota Bradenton International Airport (SRQ)

    • Los Angeles International Airport (LAX)

    • Nashville International Airport (BNA)

  • Located around 8 kilometres from the centre of Washington DC, DCA can be reached in approximately 16 minutes by car, depending on traffic. The journey by public transport takes roughly 43 minutes.

  • Want a stress-free start to your travels? Stay near Ronald Reagan National Airport. Whether you're taking an early flight from Washington DC to Chicago or just don't want to be rushed, these hotels have you covered:

Washington Dulles International Airport (IAD)

  • You can take a nonstop flight from Washington DC to Chicago jetting out of Washington Dulles International Airport (IAD). Kick off your travels at IAD and disembark at O'Hare International Airport (ORD).

  • United Airlines has direct flights from Washington DC to Chicago out of IAD. Book your favourite window (or aisle) seat and get to your destination without any detours.

  • Split up your flight from Washington DC to Chicago with a stop so you can stretch your legs or cross another place off your list. Some great stopovers between Ronald Reagan National Airport and Chicago include:

    • Sarasota Bradenton International Airport (SRQ)

    • Los Angeles International Airport (LAX)

    • Nashville International Airport (BNA)

  • On public transport, you can travel from central Washington DC to IAD in about 3 hours and 26 minutes. The airport is roughly 56 kilometres away, and getting there by car takes approximately 51 minutes.

  • Want to enjoy an extra night away before your flight from Washington DC to Chicago? Unwind in a hotel near Washington Dulles International Airport before your break officially begins. Stay at one of these accommodation options:

Arriving in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

How to find the cheapest flights from Washington DC to Chicago

  • At the moment, C$87 is the lowest price we've seen for a one-way ticket from Washington DC to Chicago. The cheapest price for a return flight is C$178. Bear in mind fares may change due to availability at the time of booking.

  • To score cheap flights from Washington DC to Chicago, reserve your journey 9 months before the departure date.

  • The cheapest month for tickets from Washington DC to Chicago is May. Compare prices using the 'Whole month' tool to find the cheapest travel date.

  • Getting a cheap ticket from Washington DC to Chicago is easy with Price Alerts. Simply create one of these automatic alerts and we'll get in touch when there's a better deal.

  • Use filters to tailor your flights from Washington DC to Chicago. Select your preferred departure and arrival times, airlines and number of stops. Alternatively, sort your results by 'Cheapest' to see the best deals.

Best time to go to Chicago

  • August is the most popular month for flights from Washington DC to Chicago. To travel when it's less crowded, go to Chicago in February.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Book your flights from Washington DC to Chicago in this month if this is the kind of weather you like.

  • Search for cheap flights from Washington DC to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

  • When it comes to looking for somewhere to rest your head, you'll find the best stays in Chicago right here. Explore these options once you've locked in your flight from Washington DC to Chicago:

  • There are so many things to see and do in this city it can be hard to know where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are major attractions which should be on any well-planned Chicago itinerary.

Complete your Chicago trip with a car rental

  • Browse our lineup of car rentals once you've booked your hotel and cheap flight from Washington DC to Chicago. Whether you want a compact ride, spacious sedan or something with all the extras, you can compare companies in one go to find the best deal.

Plan the rest of your trip from Washington D.C. to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.