Cheap flights from Washington, D.C. to Chicago from $38
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Washington, D.C. to Chicago departing on 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize 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.Find the cheapest flights from Washington, D.C. to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
American Airlines flights from Washington, D.C. to Chicago
Our best American Airlines deals on Washington, D.C. to Chicago flight tickets
Spirit Airlines flights from Washington, D.C. to Chicago
Our best Spirit Airlines deals on Washington, D.C. to Chicago flight tickets
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?
What is the cheapest month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $209. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Washington, D.C. to Chicago during January average around $229.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $402. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. to Chicago for around $495.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $337. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $456.
What is the cheapest Washington, D.C. to Chicago flight route?
Fly from Baltimore/Washington to Chicago Midway for the best Washington, D.C. - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Washington, D.C. when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $335 when searching 6 weeks out.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 $266 on momondo.
What cabin class options are available on Washington, D.C. to Chicago flights?
There are 4 cabin classes 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.
What is the cheapest airline that flies from Washington, D.C. to Chicago?
Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Washington, D.C. to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Washington, D.C. according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Washington, D.C. to Chicago on average per day?
As of April 2025, there are 58 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 47% of flights taking off at noon.
How many flights depart from Washington, D.C. to Chicago on average per week?
As of April 2025, 412 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Tue, with 27% of weekly flights taking off on this day.
When to book flights from Washington, D.C. to Chicago
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
Is flying the fastest way to get from Washington, D.C. to Chicago?
The quickest way is to book a flight from Washington, D.C. to Chicago, which can be as quick as 1h 55m onboard Southwest. You can also get a train from Washington, D.C. to Chicago, or a bus from Washington, D.C. to Chicago which can take you longer to arrive at your destination.
Is flying the cheapest way to get from Washington, D.C. to Chicago?
The cheapest way is to get a flight from Washington, D.C. to Chicago, which can be as cheap as $78. A train from Washington, D.C. to Chicago is more expensive than a flight, with prices starting at $261. A bus from Washington, D.C. to Chicago is also an option, with an average price of $120.
How far is Washington, D.C. to Chicago by plane?
The straight-line distance from Washington, D.C. to Chicago is 593.1 mi. 1h 55m is a normal flight duration for this route.
When did momondo last update prices for flights from Washington, D.C. to Chicago?
Prices for flights from Washington, D.C. to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Washington, D.C. to Chicago?
There are 6 operators available for flights from Washington, D.C. to Chicago as of April 2025.
How old do you have to be to fly from Washington, D.C. to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Washington, D.C. to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Washington, D.C. to Chicago is Airbus A319, representing 11.33% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 10.93%, Boeing 737-800 at 10.91%, and Airbus A320-100/200 at 10.88%.
What is the most popular airline from Washington, D.C. to Chicago?
momondo data reveals that the most frequently booked airline on the route from Washington, D.C. to Chicago is United Airlines, representing 33% of all bookings. The subsequent popular airlines are American Airlines at 26%, Frontier at 22%, and Southwest at 17%.
Best airlines flying from Washington, D.C. to Chicago
Compare and see reviews for airlines that fly from Washington, D.C. to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $56 | Free Cancellation | Rating 6.3 7,956 reviews | |||
| PriceFrom $58 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $98 | Free Cancellation | Rating 8.0 7,929 reviews | |||
| PriceFrom $142 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $154 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $167 | Free Cancellation | Rating 8.0 4,295 reviews |
Southwest Flights From Washington, D.C. to Chicago
Southwest flies from Washington, D.C. to Chicago around 32 times per week, with 4,295 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Washington, D.C. to Chicago in the last 72 hours was $167 (round-trip), much lower than the average airfare cost of $300 for Southwest flights on this route.
United Airlines Flights From Washington, D.C. to Chicago
The best United Airlines deal for Washington, D.C. to Chicago flight tickets found on momondo in the last 72 hours was $154, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $329 round-trip. United Airlines operates 43 flights out of Washington, D.C. into Chicago in an average week, so prices vary by time and availability. 8,696 United Airlines reviews by users on momondo have scored the airline at 7.4/10.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy 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?
Flights from Washington, D.C. to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Washington, D.C. to Chicago?
Once you have performed a search for Washington, D.C. to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Washington, D.C. are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.