Cheap flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport from $79
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. Reagan-National Airport to Chicago Midway Airport departing on 5/2. 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. Reagan-National Airport to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Frontier flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport
Our best Frontier deals on Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight tickets
Southwest flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport
Our best Southwest deals on Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Washington, D.C. Reagan-National Airport 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 cheapest month to fly to Chicago Midway Airport?
The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Washington, D.C. Reagan-National Airport, with most prices found around $235. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Washington, D.C. Reagan-National Airport during the month January is also very affordable. Most momondo users find prices during this month for around $247.
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. Reagan-National Airport. 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. Reagan-National Airport 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. Reagan-National Airport 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. Reagan-National to Chicago Midway flight route?
Fly from Washington, D.C. Reagan-National to Chicago Midway for the best Washington, D.C. Reagan-National - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Washington, D.C. Reagan-National Airport when booking 14 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $315 when searching 14 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Washington, D.C. Reagan-National Airport for as low as $224 on momondo.
What cabin class options are available on Washington, D.C. Reagan-National to Chicago Midway flights?
There are 1 cabin classes available to choose from on Washington, D.C. Reagan-National to Chicago Midway 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. Reagan-National to Chicago Midway?
Frontier, Southwest, and Delta are the most popular carriers operating from Washington, D.C. Reagan-National 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. Reagan-National Airport according to our data. Southwest is the first choice among our users, with 88% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 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. Reagan-National Airport to Chicago Midway Airport on average per day?
3 flights are operational daily from Washington, D.C. Reagan-National Airport to Chicago Midway Airport as of April 2025. The most popular departure time for this route is 6:00AM, with 54% of flights per day taking off at noon.
How many flights depart from Washington, D.C. Reagan-National Airport to Chicago Midway Airport on average per week?
As of April 2025, 22 flights take off from Washington, D.C. Reagan-National Airport and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 32% of weekly flights taking off on this day.
When to book flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport
Cheap Washington, D.C. Reagan-National Airport to Chicago Midway Airport (DCA to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport
How far is Washington, D.C. Reagan-National to Chicago Midway by plane?
Washington, D.C. Reagan-National and Chicago Midway are 598.5 mi apart from one another. By plane, this route typically takes 1h 55m.
When did momondo last update prices for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
Prices for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
As of April 2025, there are 3 operators available to choose from for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport.
How old do you have to be to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
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 layovers. It is recommended that you verify with the airline you are booking with for travel from Washington, D.C. Reagan-National Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Washington, D.C. Reagan-National Airport and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 16.59% of the total bookings. Other popular models include Boeing 737-700 Passenger/BBJ1 (winglets) with 11.91%, Boeing 737-800 with 11.84%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 11.82%.
What is the most popular airline from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Washington, D.C. Reagan-National Airport to Chicago Midway Airport is Southwest (88% of total bookings). The next most popular airlines are Frontier (7%) and Delta (5%).
Best airlines flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport
Compare and see reviews for airlines that fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $120 | Free Cancellation | Rating 5.9 3,276 reviews | |||
| PriceFrom $177 | Free Cancellation | Rating 8.0 4,276 reviews | |||
| PriceFrom $177 | Free Cancellation | Rating 8.0 7,897 reviews |
Southwest Flights From Washington, D.C. Reagan-National Airport to Chicago Midway Airport
Southwest is one of the most popular airlines flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, operating 22 flights/week on average for this route. A good Southwest flight deal for Washington, D.C. Reagan-National Airport to Chicago Midway Airport starts from $177 round-trip, up to an average price of $312. Our users have rated Southwest at 8.0/10.
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?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Washington, D.C..
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?
If you are not ready to book a flight from Washington, D.C. to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.