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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 round-trip flight from Washington, D.C. to Chicago? Find the lowest prices on one-way and round-trip tickets right here.
Chicago.AED 213 per passenger.Departing Wed, May 8, returning Wed, May 15.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Wed, May 8, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Wed, May 15, arriving in Baltimore Washington International.Price includes taxes and charges.From AED 213, select.
Chicago.AED 213 per passenger.Departing Wed, Jun 5, returning Sat, Jun 8.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Wed, Jun 5, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sat, Jun 8, arriving in Baltimore Washington International.Price includes taxes and charges.From AED 213, select.
Chicago.AED 213 per passenger.Departing Sat, Aug 24, returning Sat, Aug 31.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Sat, Aug 24, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sat, Aug 31, arriving in Baltimore Washington International.Price includes taxes and charges.From AED 213, select.
Chicago.AED 250 per passenger.Departing Sat, Aug 24, returning Sat, Sep 7.Round-trip flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departing from Baltimore Washington International on Sat, Aug 24, arriving in Chicago Midway.Inbound direct flight with Frontier Airlines departing from Chicago Midway on Sat, Sep 7, arriving in Baltimore Washington International.Price includes taxes and charges.From AED 250, 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 May.
Apr
Find prices
May
from AED 213
Jun
from AED 213
Jul
from AED 371
Aug
from AED 213
Sep
from AED 430
Oct
from AED 636
Nov
from AED 639
Dec
from AED 835
Jan
Find prices
Feb
from AED 908
Mar
from AED 824

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 foundAED 213
Cheapest month to flyMay
Average flight time2 hrs, 10 mins
Most popular airlineSouthwest Airlines
Average flights per week4,324

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 round-trip flight from Washington, D.C. to Chicago is AED 213. 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.
There are 776 flights per week flying from Washington, D.C. to Chicago, as of April 2024.
The cheapest month to fly from Washington, D.C. to Chicago is usually May.
If you're flying from Washington, D.C., the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the center of Chicago. We've found flights to this airport from AED 213.
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, May 8, 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 April, the average temperature is usually around 8°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.

The main airport in Chicago is Chicago O’Hare International Airport, while the city is also served by Chicago Midway Airport. There are five airlines operating flights from Washington to Chicago via Chicago O’Hare International Airport - American Airlines, American Eagle, Frontier Airlines, United Airlines and United Express, the shuttle service to United Airlines. Southwest Airlines operates a flight to Midway International Airport.

* This information is correct as of June 2017

Airport Information - Arriving

Chicago O’Hare International Airport is located 27km outside of Chicago and is linked to the city on the CTA Blue Line which takes between 40-50 minutes. You will find everything you would need at the airport whether it’s a café or a restaurant to enjoy a drink or a meal or shops to pick up what you need for your trip so you're sure to find some way to pass the time.

Chicago Midway Airport is the second airport in Chicago mainly operating domestic flights. The airport is a lot smaller than Chicago O’Hare International Airport but still offers an ample selection of amenities and facilities including a few shops and numerous places to eat and drink. The airport is located only 16km away from central Chicago and is connected to the city on the CTA Orange Line which takes 25 minutes.

Airport Information - Departing

Washington Dulles International Airport is the main airport serving Washington offering everything you would need for a pleasant stay. Set within a single terminal complex, the airport is home to a wide variety of shops, restaurants and cafes so you’re sure to find a way to pass the time while waiting for your flight. There are numerous bus services running to Washington Dulles International Airport from central Washington if you don’t want to drive yourself or take a taxi.

Ronald Reagan Washington National Airport is located only 5km from central Washington and is made up of three passenger terminals. You can find a variety of places to eat and drink at the airport whether it’s a café for a quick snack or a restaurant to sit down with a meal. As the airport is much closer to Washington compared to Washington Dulles International Airport you can make the journey in no time at all.

What to Expect in Chicago

In Chicago the weather is warm and pleasant over the summer but the winters in the city can be very cold and snowy so be sure to pack appropriately. As you will be on a domestic flight within the country you won’t be required to have a visa, but you still need to remember to bring all of your essential travel documents with you including your passport. Check out the top hotels in Chicago to make the most out of your visit.


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.