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151 € Cheap Flights from Washington Ronald Reagan to Chicago Midway

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Washington Ronald Reagan 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 Ronald Reagan to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from Washington Ronald Reagan Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 151 €. Find the lowest prices on one-way and return tickets right here.
      Chicago.151 € per passenger.Departing Mon, 2 Nov, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Mon, 2 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Sat, 3 Oct, returning Sat, 12 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 3 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 12 Dec, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Wed, 7 Oct, returning Wed, 14 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Wed, 7 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 14 Oct, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Mon, 8 Feb, returning Tue, 9 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Mon, 8 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 9 Feb, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Tue, 29 Sep, returning Thu, 1 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Tue, 29 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 1 Oct, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Thu, 28 Jan, returning Wed, 3 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Thu, 28 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 3 Feb, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Sat, 19 Sep, returning Sat, 12 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 19 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 12 Dec, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Mon, 14 Sep, returning Thu, 17 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Mon, 14 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 17 Sep, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Tue, 27 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Tue, 27 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.151 € per passenger.Departing Thu, 3 Dec, returning Sat, 5 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Thu, 3 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 5 Dec, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 151 €, select.
      Chicago.152 € per passenger.Departing Mon, 23 Nov, returning Tue, 1 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Mon, 23 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Dec, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 152 €, select.
      Chicago.152 € per passenger.Departing Sat, 9 Jan, returning Tue, 12 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Sat, 9 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 12 Jan, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 152 €, select.
      Chicago.193 € per passenger.Departing Mon, 21 Dec, returning Wed, 6 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Washington Ronald Reagan on Mon, 21 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 6 Jan, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 193 €, select.
      Chicago.245 € per passenger.Departing Tue, 22 Dec, returning Fri, 12 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Tue, 22 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 12 Feb, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 245 €, select.
      Chicago.268 € per passenger.Departing Thu, 31 Dec, returning Sun, 3 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Thu, 31 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 3 Jan, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 268 €, select.
      Chicago.278 € per passenger.Departing Mon, 31 Aug, returning Mon, 21 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Washington Ronald Reagan on Mon, 31 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 21 Sep, arriving in Washington Ronald Reagan.Price includes taxes and charges.From 278 €, select.

      Find the cheapest month to fly from Washington Ronald Reagan to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Washington Ronald Reagan to Chicago Midway flights are currently cheapest in September.
      Aug
      from 405 €
      Sep
      from 151 €
      Oct
      from 151 €
      Nov
      from 151 €
      Dec
      from 151 €
      Jan
      from 152 €
      Feb
      from 151 €
      Mar
      from 285 €
      Apr
      from 280 €
      May
      from 401 €
      Jun
      from 428 €
      Jul
      from 442 €

      Direct flights from Washington Ronald Reagan to Chicago Midway

      Southwest Airlines

      Washington Ronald Reagan to Chicago Midway: Alternative routes

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

      Chicago Midway

      14km from central Chicago
      Closest
      from 151 €
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from 135 €
      Search flights

      Chicago Rockford

      127km from central Chicago
      from 278 €
      Search flights

      Washington D.C. to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found151 €
      Cheapest month to flySeptember
      Average flight time2 hrs, 5 mins
      Most popular airlineSouthwest Airlines
      Average flights per week38

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

      The best price we found for a return flight from Washington Ronald Reagan to Chicago Midway is 151 €. 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 Ronald Reagan to Chicago Midway.
      Southwest Airlines flies direct from Washington Ronald Reagan to Chicago Midway.
      As of August 2026, there are 38 flights per week flying from Washington Ronald Reagan to Chicago Midway.
      The cheapest month to fly from Washington Ronald Reagan 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 Ronald Reagan Airport to Chicago Midway Airport on Tuesday, 29 September 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.

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

      Travelling from Washington Ronald Reagan Airport (DCA) to Chicago Midway Airport (MDW): what you need to know

      • Around 2 hours is how long you'll be travelling on a direct flight from Washington Ronald Reagan Airport to Chicago Midway Airport.

      • Chicago is one hour behind Washington DC and follows the UTC-6 timezone.

      • You can choose from 24 weekly Washington Ronald Reagan Airport to Chicago Midway Airport flights. The 06:00 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the latest service of the day at 21:40.

      • Your DCA to MDW flight won't wait if you're late, so get to the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

      • Travelling during a peak time such as August? Public holidays and other popular periods can lead to longer queues and delays at check-in and security. Play things extra safe and get there up to four hours ahead of international flights and two hours before a domestic departure.

      • Southwest Airlines is your gateway to exploring Chicago (and perhaps some other exciting parts of the United States!). Check out the direct flights from Washington Ronald Reagan Airport to Chicago Midway Airport offered by this airline.

      • The airline that tops the list for bookings on this route is Southwest Airlines.

      • With 75.33% of services landing as planned, Southwest Airlines is the most punctual carrier operating DCA to MDW flights.

      • If you want to explore another city along the way, simply deselect 'Direct flights only' when searching for your ticket from Washington Ronald Reagan Airport to Chicago Midway Airport. These are the most popular stopovers between DCA and MDW:

        • Detroit Wayne County Airport

        • Port Columbus Airport

        • Cleveland Hopkins International Airport

      How to find the cheapest flights from Washington Ronald Reagan Airport (DCA) to Chicago Midway Airport (MDW)

      • Currently, 76 € is the lowest price we've seen for a one-way Washington Ronald Reagan Airport to Chicago Midway Airport flight. The best price for a return plane ticket is 151 €. Remember that fares may change due to demand when booking.

      • Book two months before travelling. After looking at the numbers on our calendar, this is how far you should book ahead to find cheap tickets from DCA to MDW.

      • July is the cheapest month for flights from Washington Ronald Reagan Airport to Chicago Midway Airport. If you're looking to travel during a different time of year, the 'Whole month' tool will give you the lowest airfares across every month.

      • Finding cheap flights from DCA to MDW couldn't be easier with Price Alerts. All you need to do is create one of these automatic alerts and we'll get in touch as soon as there's a better deal.

      • Choose your preferred arrival and departure times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to see the best deals on flights from Washington Ronald Reagan Airport to Chicago Midway Airport.

      Handy information about Washington Ronald Reagan Airport (DCA)

      • DCA is located at 1 Aviation Circle.

      • When it comes to the on-time performance of Washington Ronald Reagan Airport, data shows 71% of flights arrive within the scheduled timeframe.

      • To reach Washington Ronald Reagan Airport from central Washington DC, it takes about 10 minutes if you're going by car. This depends on traffic, however. It's approximately 6 kilometres from the airport to the city centre.

      • Planning to catch public transport? Expect a journey time of around 25 minutes.

      • Have an early flight from Washington Ronald Reagan Airport to Chicago Midway Airport? Avoid the last-minute rush to the airport (and get some extra shut-eye) by picking one of these stays near DCA:

      Arriving at Chicago Midway Airport (MDW)

      • The last thing you want is a lengthy trip to your hotel if you're getting in late on a Washington Ronald Reagan Airport to Chicago Midway Airport flight. Check in to one of these accommodation options near MDW instead:

      • Grab a Chicago Midway Airport rental car and discover Chicago and beyond with your own wheels. Dollar, Hertz and Budget are leading providers to choose from here.

      • For the lowest price, reserve your ride from Chicago Midway Airport around four weeks in advance.

      When to fly to Chicago Midway Airport (MDW)

      • It's time to work out your dates for your flight from Washington Ronald Reagan Airport to Chicago Midway Airport. July is the busiest month to head to Chicago. If you want a more laid-back vibe, go in December.

      • Book your flight from Washington Ronald Reagan Airport to Chicago Midway Airport for July if you'd like to visit Chicago during its warmest month. Expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

      • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from DCA to MDW around that time if you like cooler conditions.

      Explore more of the United States

      • Columbus is just one of the many places in the United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the south-east, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Around 257 kilometres south-east of Chicago, Indianapolis is another favourite stop in the United States. Get a taste of what this destination has to offer at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

      Plan the rest of your trip from Washington D.C. to Chicago

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