Cheap Flights from Washington D.C. to Chicago Midway

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Flight deals from Washington D.C. to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Washington D.C. to Chicago Midway? Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Washington D.C. to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Washington D.C. to Chicago Midway flights are currently cheapest in April.

Direct flights from Washington D.C. to Chicago Midway

Washington D.C. to Chicago Midway: Alternative routes

Compare routes from Washington D.C. to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Washington D.C. to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs16,509
Cheapest month to flyApril
Average flight time2 hrs, 5 mins
Most popular airlineSouthwest Airlines
Average flights per week148

Finding cheap flights from Washington D.C. to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Washington D.C. to Chicago Midway is Rs32,986. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 5 minutes is the average flight time from Washington D.C. to Chicago Midway.
Southwest Airlines flies direct from Washington D.C. to Chicago Midway.
As of March 2026, there are 74 flights per week flying from Washington D.C. to Chicago Midway.
The cheapest month to fly from Washington D.C. to Chicago Midway is usually April.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Washington D.C. to Chicago Midway Airport on Saturday, 18 April 2026.
Yes – the average flight time is 2 hours and 5 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Flying from Washington DC to Chicago Midway International Airport (MDW): What you need to know

  • Kick off your journey at one of Washington DC's main airports, Ronald Reagan National Airport (DCA) or Washington Dulles International Airport (IAD). Explore your options for booking a flight from Washington DC to Chicago Midway International Airport (MDW) departing from either of these.

  • 2 hours is the average travel time for a direct Washington DC to Chicago Midway International Airport flight.

  • Chicago is one hour behind Washington DC. Chicago Midway International Airport is located in Chicago, which follows the UTC-5 timezone.

  • Ronald Reagan National Airport (DCA) to Chicago Midway International Airport (MDW) is the most popular route. There are 24 direct flights a week to pick from. If you have things to do before leaving, take the last flight with Southwest Airlines at 9:40pm. Go for the first DCA to MDW departure with Southwest Airlines at 6am if you'd rather get a move on.

  • Leave plenty of time to get on your flight from Washington DC to MDW. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Planning to travel during a peak period like a bank holiday? Expect longer queues at check-in and security. To play it safe, arrive up to four hours before international flights and two hours before domestic departures.

Airports in Washington DC

Ronald Reagan National Airport (DCA)

  • You can find a direct flight from Washington DC to Chicago Midway International Airport (MDW) leaving from Ronald Reagan National Airport (DCA).

  • Southwest Airlines is a leading airline that offers direct flights from Washington DC to Chicago Midway International Airport taking off from DCA.

  • Southwest Airlines is the airline most travellers choose for flights from DCA to MDW.

  • With 78.68% of its services landing as planned, Southwest Airlines is the most punctual carrier on this route.

  • The journey from central Washington DC to DCA takes around 45 minutes on public transport. If you ride-share, drive or grab a cab, you'll cover the 8 kilometres in 15 minutes or so, depending on traffic.

  • Looking for a comfortable hotel near Ronald Reagan National Airport? If you're catching an early flight from Washington DC to Chicago Midway International Airport, these accommodation options will have you sleeping just around the corner from the terminal:

  • When it comes to Ronald Reagan National Airport's on-time performance, data shows 76.44% of flights arrive within the expected time frame.

  • The address for DCA is 1 Aviation Circle.

Washington Dulles International Airport (IAD)

Baltimore/Wash International Thurgood Marshall Airport (BWI)

  • Start your trip at Baltimore/Wash International Thurgood Marshall Airport (BWI) and fly straight to your destination without layovers. You can book direct flights from Washington DC to Chicago Midway International Airport from here.

  • Get ready for takeoff with Southwest Airlines. It offers direct Washington DC to MDW flight tickets from BWI.

  • Southwest Airlines is the most frequently booked airline offering flights from BWI to MDW.

  • The most reliable carrier for punctuality on this route is Southwest Airlines. Its services land as scheduled 79.26% of the time.

  • BWI is roughly 48 kilometres from central Washington DC. Driving from the city centre to the airport takes about 50 minutes. If you're planning to take public transport, you can expect a journey of around 1 hour 30 minutes.

  • Make catching an early Washington DC to Chicago Midway International Airport flight one of the easiest parts of your trip. Stay at one of these hotels close to Baltimore/Wash International Thurgood Marshall Airport and head to your check-in counter with plenty of time to spare:

  • Flights departing from BWI touch down at their destination within the scheduled time frame 77.13% of the time.

About Chicago Midway International Airport (MDW)

  • If you have a late flight from Washington DC to Chicago Midway International Airport, nothing tops the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and snoozing soon after at one of these hotels near MDW:

  • Grab a Chicago Midway International Airport rental car and explore Chicago and beyond with your own wheels. Dollar, Hertz and Budget are popular providers you can book with here.

  • To secure the lowest price, book your vehicle around four weeks in advance of your Washington DC to Chicago Midway International Airport flight.

  • You'll find MDW at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • The centre of Chicago is around 14 kilometres from Chicago Midway International Airport. Journey times by car hire or cab will vary based on time of day, so do a little research before you go.

  • It takes roughly 45 minutes if you're travelling by public transport.

How to find the cheapest flights from Washington DC to Chicago Midway International Airport (MDW)

  • The lowest price we've found for a one-way ticket from Washington DC to Chicago Midway International Airport is Rs16,509. For a return flight on this route, the best price is Rs32,986. Depending on when you want to go and the availability, these fares may change.

  • Score cheap flights from Washington DC to MDW by booking two months ahead. According to our research, that's the ideal time frame for bagging a bargain.

  • Schedule your trip for July. That's the best month for landing a great bargain on Washington DC to Chicago Midway International Airport tickets. If your travel dates are flexible, use the 'Whole month' tool to find the lowest price across each month.

  • Save time searching for cheap flight tickets from Washington DC to MDW by setting up a Price Alert. We'll send you an email or notification on the app when a lower fare becomes available.

  • Filters make it easier to save some cash on your flight from Washington DC to Chicago Midway International Airport. Choose the airlines, flight times and number of stops that match your plans. Then sort the results by 'Cheapest' to bring up the lowest fares right away.

The best time to fly from Washington DC to Chicago Midway International Airport (MDW)

  • It's time to work out your travel dates for your flight from Washington DC to Chicago Midway International Airport (MDW). July is the busiest month to travel to Chicago. If you like your getaways a little more chill, go in May.

  • Before locking in your Washington DC to MDW flight ticket, consider the kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • January has temperatures of between -12ºC and 3ºC. Search for cheap tickets from Washington DC to Chicago Midway International Airport around that time if you want to travel when it's cooler.

More about Chicago

  • After booking your flight from Washington DC to Chicago Midway International Airport, find a hotel that offers the right mix of comfort and location. Make one of these options your base for exploring Chicago:

  • There are so many things to discover in this city, it can be hard to figure out where to begin. Millennium Park, Lollapalooza and Art Institute of Chicago are leading attractions which should be on every Chicago itinerary.

Explore more of the United States

  • You've seen Chicago, now it's time to explore other parts of the United States. Journey about 257 kilometres south-east to Indianapolis to check off its leading attractions. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, there's plenty to keep you busy.

  • Around 137 kilometres north of Chicago, Milwaukee is another essential stop in the United States. No visit is complete without checking out Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.