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Cheap Flights from Washington D.C. to Chicago

Compare Washington D.C. to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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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? Find the lowest prices on one-way and return tickets right here.
Chicago.$98 per passenger.Departing Sat, 24 Aug, returning Sat, 31 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Sat, 24 Aug, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Sat, 31 Aug, arriving in Baltimore Washington International.Price includes taxes and charges.From $98, select.
Chicago.$117 per passenger.Departing Tue, 14 May, returning Tue, 21 May.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Baltimore Washington International on Tue, 14 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 21 May, arriving in Baltimore Washington International.Price includes taxes and charges.From $117, select.
Chicago.$132 per passenger.Departing Wed, 25 Sep, returning Sat, 28 Sep.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Wed, 25 Sep, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Sat, 28 Sep, arriving in Baltimore Washington International.Price includes taxes and charges.From $132, select.
Chicago.$134 per passenger.Departing Wed, 5 Jun, returning Sat, 15 Jun.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Wed, 5 Jun, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Sat, 15 Jun, arriving in Baltimore Washington International.Price includes taxes and charges.From $134, select.
Chicago.$174 per passenger.Departing Wed, 10 Jul, returning Sat, 13 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Wed, 10 Jul, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Sat, 13 Jul, arriving in Baltimore Washington International.Price includes taxes and charges.From $174, select.
Chicago.$191 per passenger.Departing Fri, 31 May, returning Mon, 3 Jun.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from Baltimore Washington International on Fri, 31 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 3 Jun, arriving in Baltimore Washington International.Price includes taxes and charges.From $191, select.
Chicago.$234 per passenger.Departing Fri, 17 May, returning Mon, 20 May.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Fri, 17 May, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 20 May, arriving in Baltimore Washington International.Price includes taxes and charges.From $234, select.
Chicago.$260 per passenger.Departing Fri, 31 May, returning Mon, 3 Jun.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Baltimore Washington International on Fri, 31 May, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departs from Chicago Midway on Mon, 3 Jun, arriving in Baltimore Washington International.Price includes taxes and charges.From $260, select.

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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 August.
May
from $117
Jun
from $135
Jul
from $174
Aug
from $98
Sep
from $132
Oct
from $310
Nov
from $310
Dec
Find prices
Jan
from $435
Feb
from $472
Mar
Find prices
Apr
Find prices

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 found$98
Cheapest month to flyAugust
Average flight time2 hrs, 10 mins
Most popular airlineSouthwest Airlines
Average flights per week892

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 $98. 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 9 minutes is the average flight time from Washington D.C. to Chicago.
Southwest Airlines, United and American Airlines fly direct from Washington D.C. to Chicago.
As of May 2024, there are 892 flights per week flying from Washington D.C. to Chicago.
The cheapest month to fly from Washington D.C. to Chicago is usually August.
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 $98.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Washington D.C. to Chicago on Saturday, 24 August 2024.
Yes – the average flight time is 2 hours and 9 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 the best cheap flights from Washington D.C. to Chicago with Skyscanner Flight Search

Whether you’re looking for a one-way or return flight, compare deals on plane tickets from Washington D.C. to Chicago with all major carriers, and find the cheapest fares, using Skyscanner’s Flight Search.

  • Simply hit ‘search’ – our Flight Search tool compares prices from all major online travel agents and airlines that offer flights from Washington D.C. to Chicago to help you find the best and cheapest tickets – with no hidden fees or extra costs

  • Flex your dates – use Skyscanner’s ‘whole month’ tool to find the cheapest time to fly from Washington D.C. to Chicago within your selected dates

  • Find direct flights – tick ‘direct flights only’ to only see direct plane tickets from Washington D.C. to Chicago, if available

  • Search for nearby airports - broaden your search and potentially find even better deals for nearby airports in Washington D.C. and Chicago by selecting "add nearby airports" in the Flight Search tool

  • Book a multi-city trip – planning on visiting more than one location on your journey? Select ‘multi-city’ when searching for flights to find the best deals for stop-overs

  • Choose your flight class – compare prices for economy, business, and first class plane tickets from Washington D.C. to Chicagoand get the best deals however you choose to fly

  • Use airline points – check whether your chosen airline has a points system, such as Airpoints, to unlock flight ticket discounts and make savings on future trips from Washington D.C. to Chicago - and other destinations

Get Price Alerts to keep track of airfare changes

Score the best prices on cheap flights from Washington D.C. to Chicago with Skyscanner’s Price Alerts. Use Flight Search to find flights for your route, then click the “Get Price Alerts” button on the top left of the results page to get a notification to your phone or e-mail whenever ticket prices go up or down. For mobile users, click the bell on the top right. You can also create Price Alerts using the free Skyscanner app.

Plan your trip to Chicago all in one place with hotels and car hire

Discover the best deals on hotels and car hire in Chicago to keep all your bookings in one place and make your journey as smooth as possible. Simply use Skyscanner’s search tool to compare prices from top hotel and car providers across the country, from global to local brands.

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Book flights from Washington D.C. to Chicago with peace of mind

Fly from Washington D.C. to Chicago with peace of mind using Skyscanner’s helpful tips and resources.

  • Find flexible tickets – use Flight Search to book flexible tickets from Washington D.C. to Chicago (with eligible airlines) to protect your money if your flights are changed or cancelled

  • Keep track of travel information– make sure you check the latest travel guidance before you fly to Chicago - including visa requirements, health alerts, and more - to avoid unexpected delays

  • Check your travel insurance – make sure you have the right travel insurance before your trip from Washington D.C. to Chicago to cover you for any unexpected events, such as cancellations, delays, and lost luggage

  • Add travel cost protection - avoid travel pitfalls and choose Travel Cost Protection with Skyscanner when booking flights from Washington D.C. to Chicago. It's available at the checkout for eligible destinations

Make greener choices with sustainable flights from Washington D.C. to Chicago

Did you know that with Skyscanner Flight Search, you can filter flights from Washington D.C. to Chicago to only see routes with lower-than-average carbon emissions? Simply select "Only show flights with lower CO2 emissions" under "Greener choices" in the filter menu, or look for the "Greener Choices" label at the top of flights listings.


Read more about Skyscanner's commitment to sustainable travel

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