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Cheap Flights from Washington Dulles (IAD) to Chicago Midway (MDW)

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      Travellers and cabin class, 1 Adult, Economy

      Compare Washington Dulles to Chicago Midway flight deals

      Find the cheapest month or even day of the year to fly to Chicago Midway

      Book the best Chicago Midway fare with no extra fees

      Flight deals from Washington Dulles to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from Washington Dulles Airport to Chicago Midway Airport? If you want to travel next month, return fares start from £155. Find the lowest prices on one-way and return tickets right here.
      Chicago.£70 per passenger.Departing Wed, 30 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Wed, 30 Sep, arriving in Chicago Midway.Price includes taxes and charges.From £70, select.
      Chicago.£78 per passenger.Departing Wed, 2 Dec.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Wed, 2 Dec, arriving in Chicago Midway.Price includes taxes and charges.From £78, select.
      Chicago.£82 per passenger.Departing Wed, 7 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Wed, 7 Oct, arriving in Chicago Midway.Price includes taxes and charges.From £82, select.
      Chicago.£82 per passenger.Departing Tue, 3 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Washington Dulles on Tue, 3 Nov, arriving in Chicago Midway.Price includes taxes and charges.From £82, select.
      Chicago.£118 per passenger.Departing Wed, 20 Jan.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Wed, 20 Jan, arriving in Chicago Midway.Price includes taxes and charges.From £118, select.
      Chicago.£125 per passenger.Departing Tue, 9 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Tue, 9 Mar, arriving in Chicago Midway.Price includes taxes and charges.From £125, select.
      Chicago.£125 per passenger.Departing Tue, 4 May.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Tue, 4 May, arriving in Chicago Midway.Price includes taxes and charges.From £125, select.
      Chicago.£125 per passenger.Departing Tue, 27 Jul.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Tue, 27 Jul, arriving in Chicago Midway.Price includes taxes and charges.From £125, select.
      Chicago.£132 per passenger.Departing Tue, 8 Jun.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Tue, 8 Jun, arriving in Chicago Midway.Price includes taxes and charges.From £132, select.
      Chicago.£132 per passenger.Departing Tue, 2 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Tue, 2 Feb, arriving in Chicago Midway.Price includes taxes and charges.From £132, select.
      Chicago.£132 per passenger.Departing Wed, 14 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Washington Dulles on Wed, 14 Apr, arriving in Chicago Midway.Price includes taxes and charges.From £132, select.

      Find the cheapest month to fly from Washington Dulles to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Washington Dulles to Chicago Midway flights are currently cheapest in September.
      Sep
      from £70
      Oct
      from £82
      Nov
      from £82
      Dec
      from £78
      Jan
      from £118
      Feb
      from £132
      Mar
      from £125
      Apr
      from £132
      May
      from £125
      Jun
      from £132
      Jul
      from £125
      Aug
      Find prices

      Washington Dulles to Chicago Midway: Alternative routes

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

      Chicago Midway

      9 miles from central Chicago
      Closest
      from £70
      Search flights

      Chicago O'Hare International

      16 miles from central Chicago
      from £70
      Search flights

      Chicago Rockford

      79 miles from central Chicago
      Cheapest
      from £69
      Search flights

      Washington D.C. to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found£70
      Cheapest month to flySeptember

      Finding cheap flights from Washington Dulles to Chicago Midway: Frequently asked questions

      The best price we found for a return flight from Washington Dulles to Chicago Midway is £133. 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.
      Currently, there are no airlines that fly direct from Washington Dulles to Chicago Midway. But we found flights with one or more stops from £133.
      As of September 2026, there are no flights flying from Washington Dulles to Chicago Midway.
      The cheapest month to fly from Washington Dulles to Chicago Midway is usually September.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Washington Dulles Airport to Chicago Midway Airport on Wednesday, 23 September 2026.
      No airlines currently offer direct flights between Washington Dulles Airport and Chicago Midway Airport. Most routes have one or more stops.
      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.

      Currently, Frontier Airlines offers the cheapest flight tickets to Chicago Midway.

      Travelling from Washington Dulles Airport (IAD) to Chicago Midway Airport (MDW): what you need to know

      • The timezone in Chicago is UTC-6, which is one hour behind Washington DC.

      • To ensure you get on your IAD to MDW flight, leave enough time for things like baggage drop and finding your gate. Arriving two hours before international departures and one hour before domestic flights is the general rule.

      • During popular months like July, it's best to get to the airport earlier than usual. Arrive two hours before a domestic departure and four hours ahead for international flights whenever you're travelling during peak periods in general.

      • If you'd like to explore another city along the way, simply uncheck 'Direct flights only' when searching for your ticket from Washington Dulles Airport to Chicago Midway Airport. Here are the top stopovers between IAD and MDW:

        • Detroit Wayne County Airport

        • Pittsburgh International Airport

        • Port Columbus Airport

      Handy information about Washington Dulles Airport (IAD)

      • The address for IAD is 1 Saarinen Circle.

      • When it comes to Washington Dulles Airport's on-time performance, 77% of flights arrive within the scheduled timeframe.

      • To get to Washington Dulles Airport from central Washington DC, it'll take around 45 minutes if you're travelling by car. Of course, this depends on traffic conditions. It's approximately 40 kms (25 miles) from the airport to the city centre.

      • Planning to take public transport? Expect a trip time of around 1 hour 10 minutes.

      • Searching for a convenient hotel close to IAD? If you're boarding an early flight from Washington Dulles Airport to Chicago Midway Airport, these accommodation options will put you moments from check-in:

      Arriving at Chicago Midway Airport (MDW)

      When to fly to Chicago Midway Airport (MDW)

      • July is the most popular month for flights from Washington Dulles Airport to Chicago Midway Airport. For smaller crowds, travel to Chicago in December.

      • Book your flight from Washington Dulles Airport to Chicago Midway Airport for July if you'd like to explore Chicago during its warmest month. Expect temperatures of between 16ºC and 28ºC.

      • January sees average temperatures of between -12ºC and 3ºC. Look for cheap tickets from IAD to MDW sometime then if you'd rather travel in cooler conditions.

      Explore more of the United States

      • Chicago has its own special appeal, but there are so many other parts of the United States waiting to be explored. Around 451 kms (280 miles) south-east of Chicago, a visit to Columbus will keep you on the go. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Around 257 kms (160 miles) south-east of Chicago, Indianapolis is another essential stop in the United States. Start your sightseeing at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.