Question 1

What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?

Accepted Answer

Our cheapest airline available from Washington, D.C. to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as £121 on this airline. Additional options worth looking into are Southwest and JetBlue, starting at £122 and £141 round-trip. United Airlines is 38% cheaper than the average price of flights available within the next 90 days to this destination.

Question 2

What are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?

Accepted Answer

£62 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Frontier and Delta, with prices starting from £75 and £77, respectively.

Question 3

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

Accepted Answer

Booking 88 days in advance of your planned departure date is, on average, the best time to get cheap flights from Washington, D.C. to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

Question 4

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

Accepted Answer

Currently, January is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of £595). Flying from Washington, D.C. to Chicago in July is currently the most expensive (average of £843). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Question 5

What is the cheapest day to fly from Washington, D.C. to Chicago?

Accepted Answer

Travellers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Question 6

Weekly flight availability from Washington, D.C. to Chicago

Accepted Answer

The most flights from WAS to CHI are scheduled on a Tuesday (78 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 on average).

Question 7

E

Accepted Answer

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Question 8

E

Accepted Answer

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Question 9

What are the most popular routes from Washington, D.C. to Chicago?

Accepted Answer

While some choose either Washington, D.C. Reagan-National - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago O'Hare Intl, Baltimore/Washington - Chicago O'Hare Intl is the most popular route from Washington, D.C. to Chicago.

Question 10

What are the cheapest flights from Washington, D.C. to Chicago?

Accepted Answer

Looking at all options, your cheapest flight can be booked for £239. While the most popular route (Baltimore/Washington - Chicago O'Hare Intl) can be booked for £107 on average our data indicates £251 when flying from Washington, D.C. to Chicago.

Question 11

What are the most reliable airlines from Washington, D.C. to Chicago?

Accepted Answer

No one likes to see their flight delayed. When booking a flight from Washington, D.C. to Chicago consider choosing Sun Country Air (100%), Emirates (100%) or Austrian Airlines (88%) as they are the most reliable in getting you off to your destination on time.

Question 12

What is the cheapest day to fly round-trip from Washington, D.C. to Chicago?

Accepted Answer

Friday flights are found to be more expensive to fly from Washington, D.C. to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

Question 13

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

Accepted Answer

Travelers have found it’s best to book a flight 51 days in advance to save up to 90% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 51 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Washington, D.C. to Chicago 1-2 weeks in advance for as low as £212, or £375 for flights within the next 24 hours.

Question 14

What is the cheapest month to fly from Washington, D.C. to Chicago?

Accepted Answer

Our data shows that September tends to be the cheapest month to fly to Chicago from Washington, D.C.. Users have commonly found prices around £196 for the month, but tickets can be as low as £49. Due to multiple factors, prepare for potentially higher prices in March.

Question 15

What is the cheapest time of day to fly from WAS to CHI?

Accepted Answer

It’s optimal to fly from Washington, D.C. to Chicago in the afternoon. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the morning.

Question 16

Can I find deals for flights from Washington, D.C. to Chicago that include hotel bookings?

Accepted Answer

Yes. In addition to deals on Washington, D.C. to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

Question 17

How can I find direct flights from Washington, D.C. to Chicago?

Accepted Answer

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Washington, D.C. to Chicago.

Question 18

Can I find deals for business class flights from Washington, D.C. to Chicago?

Accepted Answer

Yes. Cheapflights offers flight deals from Washington, D.C. to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Question 19

How does Cheapflights help users find flights from Washington, D.C. to Chicago?

Accepted Answer

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Washington, D.C. to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Question 20

Why should you use Cheapflights to find cheap flight tickets from Washington, D.C. to Chicago?

Accepted Answer

Cheapflights helps you find that perfect flight to Chicago from Washington, D.C. by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Question 21

Can Cheapflights find flights from Washington, D.C. to Chicago with no change fees?

Accepted Answer

Need flexible booking options for your flight to Chicago from Washington, D.C.? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Question 22

Can Cheapflights notify me if prices for flights from Washington, D.C. to Chicago become cheaper?

Accepted Answer

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Washington, D.C. today and book when prices fit your budget.

Round-trip from	£121
One-way from	£62
Popular in	March
Cheapest in	September
Average price	£223
Good round-trip deal	£1,353 or less
Good one-way deal	£251 or less

Cheap flights from Washington, D.C. to Chicago from £62

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/5. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 88 days in advance, depart on a Tuesday or Monday and return on a Wednesday

Cheap flight deals from Washington, D.C. to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Washington, D.C. to Chicago

Cheapest flights from Washington, D.C. to ChicagoExplore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 March 2025.

Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 March 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Washington, D.C. to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington, D.C. with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. to Chicago

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

Use this chart to determine the optimal time to book a return flight from Washington, D.C. to Chicago. Price data was last updated on 21 March 2025.

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

What is the cheapest time of day to fly from WAS to CHI?

Find hourly flight availability from Washington, D.C. to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 25 March 2025.

Weekly flight availability from Washington, D.C. to Chicago

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Washington, D.C. to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?

What are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?

What are the most popular routes from Washington, D.C. to Chicago?

What are the most reliable airlines from Washington, D.C. to Chicago?

What are the cheapest flights from Washington, D.C. to Chicago?

Can I find deals for flights from Washington, D.C. to Chicago that include hotel bookings?

How can I find direct flights from Washington, D.C. to Chicago?

Can I find deals for business class flights from Washington, D.C. to Chicago?

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Other flights to Chicago

Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 25 March 2025.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Washington, D.C. to Chicago?

Why should you use Cheapflights to find cheap flight tickets from Washington, D.C. to Chicago?

Can Cheapflights find flights from Washington, D.C. to Chicago with no change fees?

Can Cheapflights notify me if prices for flights from Washington, D.C. to Chicago become cheaper?

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Washington, D.C. to Chicago
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 25 March 2025.