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237 € Cheap Flights from Richmond to Chicago Midway

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Richmond 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 Richmond to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from Richmond Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 241 €. Find the lowest prices on one-way and return tickets right here.
      Chicago.237 € per passenger.Departing Sat, 31 Oct, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Richmond on Sat, 31 Oct, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 7 Nov, arriving in Richmond.Price includes taxes and charges.From 237 €, select.
      Chicago.237 € per passenger.Departing Wed, 4 Nov, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Richmond on Wed, 4 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 7 Nov, arriving in Richmond.Price includes taxes and charges.From 237 €, select.
      Chicago.241 € per passenger.Departing Sat, 10 Oct, returning Tue, 13 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Richmond on Sat, 10 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 13 Oct, arriving in Richmond.Price includes taxes and charges.From 241 €, select.
      Chicago.241 € per passenger.Departing Thu, 3 Dec, returning Wed, 9 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Thu, 3 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 9 Dec, arriving in Richmond.Price includes taxes and charges.From 241 €, select.
      Chicago.241 € per passenger.Departing Sat, 31 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Sat, 31 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in Richmond.Price includes taxes and charges.From 241 €, select.
      Chicago.258 € per passenger.Departing Thu, 26 Nov, returning Tue, 1 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Richmond on Thu, 26 Nov, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 1 Dec, arriving in Richmond.Price includes taxes and charges.From 258 €, select.
      Chicago.275 € per passenger.Departing Mon, 5 Oct, returning Sat, 10 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Mon, 5 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 10 Oct, arriving in Richmond.Price includes taxes and charges.From 275 €, select.
      Chicago.276 € per passenger.Departing Wed, 30 Sep, returning Sat, 3 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Wed, 30 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 3 Oct, arriving in Richmond.Price includes taxes and charges.From 276 €, select.
      Chicago.276 € per passenger.Departing Wed, 18 Nov, returning Wed, 18 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Wed, 18 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 18 Nov, arriving in Richmond.Price includes taxes and charges.From 276 €, select.
      Chicago.327 € per passenger.Departing Mon, 28 Sep, returning Wed, 30 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Mon, 28 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 30 Sep, arriving in Richmond.Price includes taxes and charges.From 327 €, select.
      Chicago.343 € per passenger.Departing Wed, 30 Sep, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Richmond on Wed, 30 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 7 Nov, arriving in Richmond.Price includes taxes and charges.From 343 €, select.
      Chicago.344 € per passenger.Departing Sun, 14 Feb, returning Sat, 20 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Sun, 14 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 20 Feb, arriving in Richmond.Price includes taxes and charges.From 344 €, select.
      Chicago.360 € per passenger.Departing Thu, 6 May, returning Sun, 9 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Thu, 6 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 9 May, arriving in Richmond.Price includes taxes and charges.From 360 €, select.
      Chicago.378 € per passenger.Departing Fri, 1 Jan, returning Mon, 4 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Richmond on Fri, 1 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 4 Jan, arriving in Richmond.Price includes taxes and charges.From 378 €, select.
      Chicago.386 € per passenger.Departing Thu, 11 Mar, returning Tue, 16 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Richmond on Thu, 11 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 16 Mar, arriving in Richmond.Price includes taxes and charges.From 386 €, select.
      Chicago.387 € per passenger.Departing Tue, 29 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Richmond on Tue, 29 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 2 Jan, arriving in Richmond.Price includes taxes and charges.From 387 €, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Richmond to Chicago Midway found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Richmond to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Richmond to Chicago Midway flights are currently cheapest in November.
      Sep
      from 327 €
      Oct
      from 241 €
      Nov
      from 237 €
      Dec
      from 241 €
      Jan
      from 378 €
      Feb
      from 344 €
      Mar
      from 386 €
      Apr
      from 395 €
      May
      from 360 €
      Jun
      Find prices
      Jul
      Find prices
      Aug
      Find prices

      Direct flights from Richmond to Chicago Midway

      Southwest Airlines

      Richmond to Chicago Midway: Alternative routes

      Compare routes from Richmond 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 237 €
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from 224 €
      Search flights

      Chicago Rockford

      127km from central Chicago
      from 273 €
      Search flights

      Richmond to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found237 €
      Cheapest month to flyOctober
      Average flight time2 hrs, 5 mins
      Most popular airlineSouthwest Airlines
      Average flights per week9

      Finding cheap flights from Richmond to Chicago Midway: Frequently asked questions

      The best price we found for a return flight from Richmond to Chicago Midway is 237 €. 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 Richmond to Chicago Midway.
      Southwest Airlines flies direct from Richmond to Chicago Midway.
      As of September 2026, there are 9 flights per week flying from Richmond to Chicago Midway.
      The cheapest month to fly from Richmond to Chicago Midway is usually October.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Richmond Airport to Chicago Midway Airport on Saturday, 31 October 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.

      Flying from Richmond Airport (RIC) to Chicago Midway Airport (MDW): what you need to know

      • Around 2 hours is how long you can expect to be in the air on a direct flight from Richmond Airport to Chicago Midway Airport.

      • Chicago's timezone is UTC-6, which makes Chicago one hour behind Richmond.

      • You can choose from five weekly Richmond Airport to Chicago Midway Airport flights. The 05:25 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the last service of the day at 20:30.

      • To ensure you catch your RIC to MDW flight, leave enough time for things like baggage drop and finding your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the standard rule.

      • During popular months such as July, you'll want to get to the airport earlier than usual. Arrive two hours before domestic departures and four hours ahead of international flights whenever you're travelling during a high season in general.

      • Southwest Airlines has direct flights from Richmond Airport to Chicago Midway Airport. Book with this popular airline, then get ready to check out the sights in Chicago — and maybe even more of the United States if time allows.

      • Most passengers choose to travel with Southwest Airlines on this route.

      • The most punctual carrier offering RIC to MDW flights is Southwest Airlines. Its services land without delay 72.73% of the time.

      • Think about adding a stopover when booking your ticket from Richmond Airport to Chicago Midway Airport. Simply uncheck 'Direct flights only' to break up your journey, or even explore someplace new along the way. Here are some options between RIC and MDW:

        • Detroit Wayne County Airport

        • Philadelphia International Airport

        • Baltimore Washington International Airport

      How to find the cheapest flights from Richmond Airport (RIC) to Chicago Midway Airport (MDW)

      • The lowest price we've found for a one-way Richmond Airport to Chicago Midway Airport flight is 112 €. A round-trip ticket right now is 237 €. Depending on the availability when you book, these fares can change.

      • Score cheap tickets from RIC to MDW by booking at least two months ahead. According to our research, that's the sweet spot for bagging a bargain.

      • The cheapest month for flights from Richmond Airport to Chicago Midway Airport is July. Use the 'Whole month' tool to find the lowest airfares if you have flexible dates.

      • You don't need to check back in every day to find out if fares have gone down when you set up a Price Alert. We'll let you know as soon as there's a change in price on cheap flights from RIC to MDW.

      • Tailor your flights with filters. Pick your ideal departure and arrival times, total journey duration and airlines. You can also sort the results by 'Fastest,' 'Best' or 'Cheapest' flights from Richmond Airport to Chicago Midway Airport.

      Handy information about Richmond Airport (RIC)

      • RIC is located at 1 Richard E. Byrd Terminal Drive.

      • 74% of flights taking off from Richmond Airport make it to their destination on time.

      • Central Richmond to Richmond Airport is approximately 14 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're catching a taxi, ride-sharing or driving.

      • You can expect a trip time of around 50 minutes on public transport.

      • Need a convenient hotel close to RIC? If you're catching an early flight from Richmond Airport to Chicago Midway Airport, these accommodation options will put you moments from your departure lounge:

      Arriving at Chicago Midway Airport (MDW)

      • If you're arriving on a late Richmond Airport to Chicago Midway Airport flight, few things top the convenience of staying near the terminal. Collect your bags from the carousel and then be showered and relaxing not long after at one of these accommodation options near MDW:

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

      • For the best deal, reserve your ride from Chicago Midway Airport about four weeks ahead.

      When to fly to Chicago Midway Airport (MDW)

      • July is the most popular month for flights from Richmond Airport to Chicago Midway Airport. To steer clear of the crowds, go to Chicago in December.

      • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your flights from Richmond Airport to Chicago Midway Airport in this month if this is the type of weather you enjoy.

      • If you like cooler conditions, look for a cheap ticket from RIC to MDW in January. Temperatures average between -12ºC (10ºF) and 3ºC (37ºF) then.

      Explore more of the United States

      • You've done Chicago, now it's time to explore other parts of the United States. Journey around 451 kilometres south-east to Columbus to tick off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, there's plenty to keep you busy.

      • Around 257 kilometres 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.

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