Cheap flights from Washington, D.C. to Chicago from $39
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 6/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Frontier flights from Washington, D.C. to Chicago Midway Airport
Our best Frontier deals on Washington, D.C. to Chicago Midway Airport flight tickets
Delta flights from Washington, D.C. to Chicago Midway Airport
Our best Delta deals on Washington, D.C. to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Washington, D.C. to Chicago Midway Airport
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 Midway Airport?
What is the cheapest month to fly to Chicago Midway Airport?
The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C., with most prices found around $181. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Washington, D.C. during the month September is also very affordable. Most momondo users find prices during this month for around $186.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Washington, D.C.. The lowest ticket price found for a Thursday departure recently was $336. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Washington, D.C. because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $412.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Washington, D.C. in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $338 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $359. 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 Midway flight route?
Fly from Baltimore/Washington to Chicago Midway for the best Washington, D.C. - Chicago Midway flight prices
What cabin class options are available on Washington, D.C. to Chicago Midway flights?
There are 1 cabin classes available to choose from on Washington, D.C. to Chicago Midway 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 Midway Airport flight prices changed over time?
As of May 2025, prices for Washington, D.C. to Chicago Midway Airport flights are approximately 52% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Washington, D.C. to Chicago Midway?
Frontier, Southwest, and Allegiant Air are the most popular carriers operating from Washington, D.C. to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Washington, D.C. according to our data. Southwest is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Washington, D.C. to Chicago Midway Airport on average per day?
10 flights are operational daily from Washington, D.C. to Chicago Midway Airport as of May 2025. The most popular departure time for this route is 5:00PM, with 44% of flights per day taking off at noon.
How many flights depart from Washington, D.C. to Chicago Midway Airport on average per week?
As of May 2025, there are 73 flights per week flying from Washington, D.C. to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.
When to book flights from Washington, D.C. to Chicago Midway Airport
Cheap Washington, D.C. to Chicago Midway Airport (WAS to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. to Chicago Midway Airport
How far is Washington, D.C. to Chicago Midway by plane?
Washington, D.C. and Chicago Midway are 597.2 mi apart from one another. In terms of flight time, this usually takes a little over 1h 55m.
When did momondo last update prices for flights from Washington, D.C. to Chicago Midway Airport?
Prices for flights from Washington, D.C. to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Washington, D.C. to Chicago Midway Airport?
As of May 2025, there are 4 operators available to choose from for flights from Washington, D.C. to Chicago Midway Airport.
How old do you have to be to fly from Washington, D.C. to Chicago Midway Airport?
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 Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport 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 license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. 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 Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Washington, D.C. to Chicago Midway Airport is Boeing 737 MAX 8 (14.74% of total bookings). The next most popular plane models are Boeing 737-800 Passenger/BBJ2 (winglets) (12.32%), Boeing 737-700 Passenger/BBJ1 (winglets) (11.46%), and Airbus A319 (10.65%).
What is the most popular airline from Washington, D.C. to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Washington, D.C. to Chicago Midway Airport is Southwest (50% of total bookings). The next most popular airlines are Frontier (37%), Delta (5%), and American Airlines (4%).
Best airlines flying from Washington, D.C. to Chicago Midway Airport
Compare and see reviews for airlines that fly from Washington, D.C. to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $58 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $98 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $161 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $177 | Free Cancellation | Rating 8.0 4,294 reviews |
Southwest Flights From Washington, D.C. to Chicago Midway Airport
The lowest priced Southwest flight from Washington, D.C. to Chicago Midway Airport from the last 72 hours was $177. Generally, Southwest has 32 flights on this route every week with an average price of $307. Southwest is rated 8.0/10 by our users.
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Why should I use momondo to find a flight deal from Washington, D.C. to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Washington, D.C. to Chicago. Millions of users trust and use momondo every year so you are in good hands.
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?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Washington, D.C..
I’m not ready to book a flight from Washington, D.C. to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Washington, D.C.. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.