Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Washington, D.C. to Chicago from R2 435

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Washington, D.C. to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
United Airlines Logo
22:18 - 23:32IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 14mdirect
United Airlines Logo
14:37 - 17:44ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 07mdirect
R4 853United Airlines
Thu, Oct 22 - Sat, Oct 24
United Airlines Logo
22:18 - 23:32IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 14mdirect
United Airlines Logo
8:50 - 11:52ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 02mdirect
R5 033United Airlines
Fri, Oct 23 - Wed, Oct 28
Delta Logo
15:00 - 19:05IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 05m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:38 - 23:21ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
9h 43m1 stop Minneapolis St Paul
R5 049Delta
Thu, Nov 12 - Sat, Nov 14
United Airlines Logo
13:10 - 14:26IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 16mdirect
United Airlines Logo
18:06 - 21:11ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 05mdirect
R5 066United Airlines
Fri, Oct 16 - Sat, Oct 17
United Airlines Logo
8:15 - 9:37IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 22mdirect
United Airlines Logo
18:15 - 21:18ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 03mdirect
R5 098United Airlines
Tue, Dec 1 - Tue, Dec 1
United Airlines Logo
22:15 - 23:29IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 14mdirect
United Airlines Logo
8:52 - 11:53ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 01mdirect
R5 115United Airlines
Thu, Dec 3 - Mon, Dec 7
Delta Logo
12:20 - 16:26IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 06m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:10 - 11:50ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
4h 40m1 stop New York John F Kennedy Intl
R5 180Delta
Sat, Oct 24 - Mon, Oct 26
United Airlines Logo
13:15 - 14:38IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 23mdirect
United Airlines Logo
8:52 - 11:53ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
2h 01mdirect
R5 196United Airlines
Tue, Nov 24 - Tue, Dec 1
United Airlines Logo
22:18 - 23:32IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
2h 14mdirect
United Airlines Logo
21:41 - 0:30ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
1h 49mdirect
R5 213United Airlines
Fri, Oct 23 - Fri, Oct 30
Delta Logo
12:27 - 16:58IAD  Washington, D.C. Dulles Intl-ORD Chicago O'Hare Intl
5h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:20 - 23:26ORD  Chicago O'Hare Intl-IAD Washington, D.C. Dulles Intl
16h 06m1 stop Minneapolis St Paul
R5 229Delta
Fri, Oct 30 - Sat, Oct 31

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

United Airlines flights from Washington, D.C. to Chicago

Our best United Airlines deals on Washington, D.C. to Chicago flight tickets
United Airlines
Oct 22
IAD22:18Washington, D.C. Dulles Intl
2h 14m
ORD23:32Chicago O'Hare Intl
Oct 24
ORD14:37Chicago O'Hare Intl
2h 07m
IAD17:44Washington, D.C. Dulles Intl
R4 853
United Airlines
Oct 23
IAD22:18Washington, D.C. Dulles Intl
2h 14m
ORD23:32Chicago O'Hare Intl
Oct 28
ORD8:50Chicago O'Hare Intl
2h 02m
IAD11:52Washington, D.C. Dulles Intl
R5 033
United Airlines
Oct 16
IAD13:10Washington, D.C. Dulles Intl
2h 16m
ORD14:26Chicago O'Hare Intl
Oct 17
ORD18:06Chicago O'Hare Intl
2h 05m
IAD21:11Washington, D.C. Dulles Intl
R5 066

Delta flights from Washington, D.C. to Chicago

Our best Delta deals on Washington, D.C. to Chicago flight tickets
Delta
Nov 12
IAD15:00Washington, D.C. Dulles Intl
5h 05m
1 stop
ORD19:05Chicago O'Hare Intl
Nov 14
ORD12:38Chicago O'Hare Intl
9h 43m
1 stop
IAD23:21Washington, D.C. Dulles Intl
R5 049
Delta
Oct 24
IAD12:20Washington, D.C. Dulles Intl
5h 06m
1 stop
ORD16:26Chicago O'Hare Intl
Oct 26
ORD6:10Chicago O'Hare Intl
4h 40m
1 stop
IAD11:50Washington, D.C. Dulles Intl
R5 180
Delta
Oct 30
IAD12:27Washington, D.C. Dulles Intl
5h 31m
1 stop
ORD16:58Chicago O'Hare Intl
Oct 31
ORD6:20Chicago O'Hare Intl
16h 06m
1 stop
IAD23:26Washington, D.C. Dulles Intl
R5 229

momondo Fare Finder

 
Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest return flight

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 22/10

22:18-23:32

Nonstop2h 14m

Chicago O'Hare Intl

Sat 24/10

14:37-17:44

Nonstop2h 07m

R4 853

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Fri 23/10

22:18-23:32

Nonstop2h 14m

Chicago O'Hare Intl

Wed 28/10

8:50-11:52

Nonstop2h 02m

R5 033

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 12/11

15:00-19:05

1 stop5h 05m

Chicago O'Hare Intl

Sat 14/11

12:38-23:21

1 stop9h 43m

R5 049

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Fri 16/10

13:10-14:26

Nonstop2h 16m

Chicago O'Hare Intl

Sat 17/10

18:06-21:11

Nonstop2h 05m

R5 066

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 1/12

8:15-9:37

Nonstop2h 22m

Chicago O'Hare Intl

Tue 1/12

18:15-21:18

Nonstop2h 03m

R5 098

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Thu 3/12

22:15-23:29

Nonstop2h 14m

Chicago O'Hare Intl

Mon 7/12

8:52-11:53

Nonstop2h 01m

R5 115

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Sat 24/10

12:20-16:26

1 stop5h 06m

Chicago O'Hare Intl

Mon 26/10

6:10-11:50

1 stop4h 40m

R5 180

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Tue 24/11

13:15-14:38

Nonstop2h 23m

Chicago O'Hare Intl

Tue 1/12

8:52-11:53

Nonstop2h 01m

R5 196
Fastest return journey

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Fri 23/10

22:18-23:32

Nonstop2h 14m

Chicago O'Hare Intl

Fri 30/10

21:41-0:30

Nonstop1h 49m

R5 213

Washington, D.C.Chicago

IAD Washington, D.C. Dulles Intl - ORD Chicago O'Hare Intl

IADORD

Washington, D.C. Dulles Intl

Fri 30/10

12:27-16:58

1 stop5h 31m

Chicago O'Hare Intl

Sat 31/10

6:20-23:26

1 stop16h 06m

R5 229

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Washington, D.C. to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Washington, D.C. and Chicago?

Prices are currently typical for flights on this route.

Typical prices usually range from R3 170 to R5 736.
The lowest price recently found on this route was R4 853.

What is the cheapest month to fly to Chicago?

The month of January is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around R4 788. If you are unable to visit Chicago during the month of January, then departing from Washington, D.C. during the month February is also very affordable. Most momondo users find prices during this month for around R4 886.

What is the cheapest day to depart on your flight to Chicago?

On average, the least expensive day to fly to Chicago from Washington, D.C. is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as R6 252. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Thursday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Thursday is R9 357.

What is the cheapest time of day to depart on your flight to Chicago?

Our data shows that the cheapest Washington, D.C. to Chicago flights are usually those with departure times in the morning. Our users have found flights to Chicago in the morning for as low as R6 252. Try not to purchase tickets in the afternoon because they tend to be around R8 275. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Washington, D.C. to Chicago flight route?

Fly from Washington, D.C. Reagan-National to Chicago Midway for the best Washington, D.C. - Chicago flight prices

How far in advance should I book a flight from Washington, D.C. to Chicago?

You are more likely to see cheaper flights to Chicago from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around R6 609 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. for as low as R4 935 on momondo.

What cabin class options are available on Washington, D.C. to Chicago flights?

There is only 1 cabin class available to choose from on Washington, D.C. to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Washington, D.C. to Chicago flight prices changed over time?

As of September 2026, prices for Washington, D.C. to Chicago flights are approximately 15% cheaper when compared to flights at the same time last year.

When to book flights from Washington, D.C. to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Washington, D.C. to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Washington, D.C. to Chicago (WAS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago

Best price found

R2 435

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Washington, D.C. in the past 72 hours is R2 435. The best return flight deal from Washington, D.C. to Chicago found on momondo in the last 72 hours is R4 853.
Direct flights go from Washington, D.C. to Chicago every day.
There are 3 airports in Chicago. From Washington, D.C. there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Washington, D.C. to Chicago

  • How far is Washington, D.C. to Chicago by plane?

    Washington, D.C. and Chicago are 954,5 km apart from one another.

  • When did momondo last update prices for flights from Washington, D.C. to Chicago?

    Prices for flights from Washington, D.C. to Chicago are updated daily.

  • How old do you have to be to fly from Washington, D.C. to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Washington, D.C. to Chicago?

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond

Why use momondo?

Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?

It is quick and easy to find Washington, D.C. to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Washington, D.C. to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Washington, D.C. with this policy.

How can momondo help me find flights from Washington, D.C. to Chicago?

momondo helps you find the best flight between Washington, D.C. and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Washington, D.C. to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago trip

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 26/10
Mon 2/11
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport
Chicago O'Hare Intl Airport