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Cheap Flights from Washington D.C. to Chicago

Travellers and cabin class

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? Find the lowest prices on one-way and return tickets right here.
Chicago.CHF 33 per passenger.Departing Sun, 1 Jun.One-way flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Baltimore Washington International on Sun, 1 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From CHF 33, select.
Chicago.CHF 39 per passenger.Departing Mon, 4 Aug.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Mon, 4 Aug, arriving in Chicago Midway.Price includes taxes and charges.From CHF 39, select.
Chicago.CHF 41 per passenger.Departing Fri, 25 Jul.One-way flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Fri, 25 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From CHF 41, select.
Chicago.CHF 50 per passenger.Departing Wed, 5 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Wed, 5 Nov, arriving in Chicago Midway.Price includes taxes and charges.From CHF 50, select.
Chicago.CHF 50 per passenger.Departing Wed, 1 Oct.One-way flight with United.Outbound direct flight with United departs from Washington Ronald Reagan on Wed, 1 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From CHF 50, select.
Chicago.CHF 50 per passenger.Departing Sat, 27 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Sat, 27 Sep, arriving in Chicago Midway.Price includes taxes and charges.From CHF 50, select.
Chicago.CHF 58 per passenger.Departing Sun, 25 May.One-way flight with Spirit Airlines.Outbound direct flight with Spirit Airlines departs from Baltimore Washington International on Sun, 25 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From CHF 58, select.
Chicago.CHF 95 per passenger.Departing Tue, 2 Dec.One-way flight with United.Outbound direct flight with United departs from Washington Dulles on Tue, 2 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From CHF 95, 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 CHF 58
Jun
from CHF 33
Jul
from CHF 41
Aug
from CHF 39
Sep
from CHF 50
Oct
from CHF 50
Nov
from CHF 50
Dec
from CHF 95
Jan
from CHF 95
Feb
from CHF 103
Mar
from CHF 124
Apr
from CHF 95

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 foundCHF 33
Cheapest month to flyJune
Average flight time2 hrs, 12 mins
Most popular airlineSouthwest Airlines
Average flights per week3,612

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 CHF 67. 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 11 minutes is the average flight time from Washington D.C. to Chicago.
Southwest Airlines, United and Alaska Airlines fly direct from Washington D.C. to Chicago.
As of May 2025, there are 903 flights per week flying from Washington D.C. to Chicago.
The cheapest month to fly from Washington D.C. to Chicago is usually May 2025.
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 CHF 67.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Washington D.C. to Chicago on Wednesday, 16 July 2025.
Yes – the average flight time is 2 hours and 11 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 .

How to find cheap flights to Chicago from Washington D.C.

Looking for cheap tickets from Washington D.C. to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Washington D.C. to Chicago. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Chicago from Washington D.C. from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
  • Flex your dates to find the best Washington D.C.-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from Washington D.C..
  • Set up a Price Alert. You can easily track the fare of your cheap Washington D.C.-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between Washington D.C. and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from Washington D.C. and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for Washington D.C. to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

    • Combine your flight to Chicago from Washington D.C. with hotels and car hire

    Once you've secured your cheap flight ticket from Washington D.C. to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.


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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.