Cheap Flights from Washington D.C. to Chicago Midway

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Find the cheapest month or even day of the year to fly 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 Airport? If you want to travel next month, return fares start from R 2,879. Find the lowest prices on one-way and return tickets right here.

Chicago.R 1,386 per passenger.Departing Tue, 11 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Baltimore Washington International on Tue, 11 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 1,386, select.

Chicago.R 1,432 per passenger.Departing Tue, 20 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Baltimore Washington International on Tue, 20 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 1,432, select.

Chicago.R 1,439 per passenger.Departing Wed, 8 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Wed, 8 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 1,439, select.

Chicago.R 1,439 per passenger.Departing Tue, 4 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Tue, 4 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 1,439, select.

Chicago.R 1,440 per passenger.Departing Wed, 14 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Wed, 14 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 1,440, select.

Chicago.R 1,440 per passenger.Departing Tue, 8 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Tue, 8 Sep, arriving in Chicago Midway.Price includes taxes and charges.From R 1,440, select.

Chicago.R 1,479 per passenger.Departing Wed, 11 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Wed, 11 Nov, arriving in Chicago Midway.Price includes taxes and charges.From R 1,479, select.

Chicago.R 1,763 per passenger.Departing Tue, 30 Jun.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Ronald Reagan on Tue, 30 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 1,763, select.

Chicago.R 1,945 per passenger.Departing Mon, 14 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Baltimore Washington International on Mon, 14 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 1,945, select.

Chicago.R 1,952 per passenger.Departing Mon, 14 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Mon, 14 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 1,952, select.

Chicago.R 2,287 per passenger.Departing Tue, 30 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Tue, 30 Jun, arriving in Chicago Midway.Price includes taxes and charges.From R 2,287, select.

Chicago.R 2,289 per passenger.Departing Sat, 16 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Sat, 16 Jan, arriving in Chicago Midway.Price includes taxes and charges.From R 2,289, select.

Chicago.R 2,447 per passenger.Departing Sat, 24 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Baltimore Washington International on Sat, 24 Apr, arriving in Chicago Midway.Price includes taxes and charges.From R 2,447, select.

Chicago.R 2,448 per passenger.Departing Wed, 31 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Baltimore Washington International on Wed, 31 Mar, arriving in Chicago Midway.Price includes taxes and charges.From R 2,448, select.

Chicago.R 2,514 per passenger.Departing Fri, 26 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Baltimore Washington International on Fri, 26 Feb, arriving in Chicago Midway.Price includes taxes and charges.From R 2,514, select.

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 August.

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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 found	R 1,386
Cheapest month to fly	August
Average flight time	2 hrs, 4 mins
Most popular airline	Southwest Airlines
Average flights per week	87

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

How much are return flights from Washington D.C. to Chicago Midway?

The best price we found for a return flight from Washington D.C. to Chicago Midway is R 2,794. 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.

How long does it take to fly from Washington D.C. to Chicago Midway?

2 hours and 4 minutes is the average flight time from Washington D.C. to Chicago Midway.

Which airlines fly direct from Washington D.C. to Chicago Midway?

Southwest Airlines flies direct from Washington D.C. to Chicago Midway.

How many flights are there a week from Washington D.C. to Chicago Midway?

As of June 2026, there are 87 flights per week flying from Washington D.C. to Chicago Midway.

When is the cheapest time to fly from Washington D.C. to Chicago Midway?

The cheapest month to fly from Washington D.C. to Chicago Midway is usually September.

Which upcoming date is cheapest to fly from Washington D.C. to Chicago Midway Airport on?

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 Wednesday, 30 September 2026.

Can I get a direct flight from Washington D.C. to Chicago Midway Airport?

Yes – the average flight time is 2 hours and 4 minutes.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

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.

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

Start your trip planning by checking out the best place to catch your flight from Washington DC to Chicago Midway International Airport (MDW). Explore your options for setting off from Ronald Reagan Washington National Airport (DCA) or Baltimore Washington International Airport (BWI), the city's main airports.
Expect to be in the air for 2 hours 5 minutes. On average, that's the time it takes for a direct Washington DC to Chicago Midway International Airport flight.
The timezone in Chicago is UTC-6, which is one hour behind Washington DC. Chicago Midway International Airport is located in Chicago.
Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW) is the most popular route. There are 30 direct weekly departures to pick from. If you have things to do before heading off, hop on the last flight with Southwest Airlines at 9:40pm. Choose the first DCA to MDW departure with Southwest Airlines at 6am if you'd rather get a move on.
For stress-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you enough time to board your flight from Washington DC to MDW.
Travelling during a peak time like July? High seasons (like Christmas/New Year and spring break) can easily add another hour at check-in and security. Play things extra safe and arrive up to four hours before international flights and two hours before domestic departures.

Airports in Washington DC

Ronald Reagan Washington National Airport (DCA)

You can hop on a direct flight from Washington DC to Chicago Midway International Airport (MDW) departing from Ronald Reagan Washington National Airport (DCA).
When jetting out of DCA, you can catch a direct flight from Washington DC to Chicago Midway International Airport with Southwest Airlines.
Southwest Airlines is the most frequently chosen airline for flights from DCA to MDW.
The carrier with the most reliable on-time performance on this route is Southwest Airlines. Its services land without delay 75.33% of the time.
DCA is about 6 kilometres from central Washington DC. If you're catching a taxi, ride-sharing or driving from the centre, it'll take 10 minutes or so to get there, depending on traffic. If you're taking public transport, expect the travel time to be around 25 minutes.
Booked an early flight from Washington DC to Chicago Midway International Airport? Avoid the hassle of rushing to the terminal (and sneak in some extra precious sleep) by choosing one of these stays close to Ronald Reagan Washington National Airport:
When it comes to the on-time performance of Ronald Reagan Washington National Airport, 71% of flights meet their scheduled arrival time.
You'll find DCA at 1 Aviation Circle.

Washington Dulles International Airport (IAD)

You can arrive at IAD from central Washington DC in approximately 45 minutes by car, depending on traffic. The journey by public transport takes roughly 1 hour 10 minutes to cover the 40 kilometres or so.
Get a head start on your holiday with an additional night away from home. Before catching your Washington DC to MDW flight, unwind in one of these hotels close to Washington Dulles International Airport:
77% of all departures from Washington Dulles International Airport stick to their scheduled arrival time.
IAD is located at 1 Saarinen Circle.

Baltimore Washington International Airport (BWI)

Kick off your adventure at Baltimore Washington International Airport (BWI) and head straight to your destination without any stops. You can book direct flights from Washington DC to Chicago Midway International Airport out of here.
You can fly out of BWI with Southwest Airlines. This leading carrier offers direct Washington DC to MDW plane tickets.
Southwest Airlines is the airline most travellers choose for flights from BWI to MDW.
With 77.26% of services arriving as planned, Southwest Airlines is the best performing carrier for punctuality on this route.
BWI is around 48 kilometres from central Washington DC. The drive from the city centre to the terminal takes about 40 minutes. If you're planning to use public transport, you can expect a journey of around 50 minutes.
Make departure day worry-free — stay near Baltimore Washington International Airport and know you'll get to the terminal with time to spare. Get settled at one of these hotels the day before if you're catching an early Washington DC to Chicago Midway International Airport flight:
The on-time performance record of BWI is 77%. To put it simply, that's how often flights departing this airport arrive as planned.

About Chicago Midway International Airport (MDW)

Have a late flight from Washington DC to Chicago Midway International Airport? Don't let it steal your sleep. Check in to one of these hotels near MDW and give yourself a well-earned lights-out:
For the best deal, book your vehicle around four weeks in advance of your Washington DC to Chicago Midway International Airport flight.
MDW is located at 5700 South Cicero.

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

Chicago Midway International Airport is around 16 kilometres from central Chicago. It takes around 25 minutes or so to drive to the city.
If you're travelling by public transport, expect a journey time of about 30 minutes.

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

R 1,384 is the best price for a one-way ticket from Washington DC to Chicago Midway International Airport. Return flights start at R 2,794. These fares may change depending on demand and availability.
Get your hands on cheap flights from Washington DC to MDW by booking two months ahead. Based on our research, that's the ideal time frame for picking up a bargain.
The best month for scoring cheap Washington DC to Chicago Midway International Airport tickets is July. Use the 'Whole month' tool to compare prices, then select the dates that offer the biggest savings.
There's no need to check back in every day to find out if prices have dropped when you set up a Price Alert. We'll let you know the moment a lower fare pops up on plane tickets from Washington DC to MDW.
Find a cheap flight from Washington DC to Chicago Midway International Airport by using the search filters. Select your ideal times, airlines and number of stops, then sort the results by 'Cheapest' for the best deals.

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

Picture the kind of break you want when deciding the best time to fly. November is the quietest month to go to Chicago. July is when most people book flights from Washington DC to Chicago Midway International Airport (MDW), which may be ideal if you're chasing more action.
Before locking in your Washington DC to MDW plane ticket, consider the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).
January has temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from Washington DC to Chicago Midway International Airport around that time if you want to travel in cooler conditions.

More about Chicago

Start your Chicago trip right by choosing the ideal place to stay. Once you've booked your flight from Washington DC to Chicago Midway International Airport, check out our selection of hotels including:
You'll find plenty of things to do in Chicago when you're ready to sightsee. Start exploring at Millennium Park followed by Art Institute of Chicago and Willis Tower.

Explore more of the United States

Indianapolis is just one of the many cities in the United States waiting to be explored once you've seen the sights of Chicago. Around 257 kilometres away to the southeast, its best attractions include Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.
If you're eager to discover another major destination in the United States, consider Milwaukee, roughly 137 kilometres north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are among its highlights.