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Cheap flights from Raleigh / Durham to Chicago Midway

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Raleigh / Durham 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 Raleigh / Durham to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from Raleigh / Durham Airport to Chicago Midway Airport? If you want to travel next month, return fares start from P11,571. Find the lowest prices on one-way and return tickets right here.
      Chicago.P5,323 per passenger.Departing Fri, 2 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Fri, 2 Oct, arriving in Chicago Midway.Price includes taxes and charges.From P5,323, select.
      Chicago.P5,841 per passenger.Departing Wed, 30 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Wed, 30 Sep, arriving in Chicago Midway.Price includes taxes and charges.From P5,841, select.
      Chicago.P6,902 per passenger.Departing Fri, 6 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Fri, 6 Nov, arriving in Chicago Midway.Price includes taxes and charges.From P6,902, select.
      Chicago.P7,188 per passenger.Departing Wed, 2 Dec.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Wed, 2 Dec, arriving in Chicago Midway.Price includes taxes and charges.From P7,188, select.
      Chicago.P8,224 per passenger.Departing Thu, 12 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Thu, 12 Nov, arriving in Chicago Midway.Price includes taxes and charges.From P8,224, select.
      Chicago.P8,225 per passenger.Departing Wed, 7 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Wed, 7 Oct, arriving in Chicago Midway.Price includes taxes and charges.From P8,225, select.
      Chicago.P8,225 per passenger.Departing Mon, 21 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Mon, 21 Dec, arriving in Chicago Midway.Price includes taxes and charges.From P8,225, select.
      Chicago.P8,228 per passenger.Departing Mon, 28 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Mon, 28 Sep, arriving in Chicago Midway.Price includes taxes and charges.From P8,228, select.
      Chicago.P8,231 per passenger.Departing Thu, 11 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Thu, 11 Feb, arriving in Chicago Midway.Price includes taxes and charges.From P8,231, select.
      Chicago.P10,684 per passenger.Departing Wed, 7 Jul.One-way flight with Delta.Outbound indirect flight with Delta, departs from Raleigh / Durham on Wed, 7 Jul, arriving in Chicago Midway.Price includes taxes and charges.From P10,684, select.
      Chicago.P10,692 per passenger.Departing Sun, 31 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Sun, 31 Jan, arriving in Chicago Midway.Price includes taxes and charges.From P10,692, select.
      Chicago.P11,108 per passenger.Departing Sun, 30 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Sun, 30 Aug, arriving in Chicago Midway.Price includes taxes and charges.From P11,108, select.
      Chicago.P11,928 per passenger.Departing Fri, 19 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Raleigh / Durham on Fri, 19 Mar, arriving in Chicago Midway.Price includes taxes and charges.From P11,928, select.
      Chicago.P12,558 per passenger.Departing Fri, 19 Mar.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Fri, 19 Mar, arriving in Chicago Midway.Price includes taxes and charges.From P12,558, select.
      Chicago.P15,393 per passenger.Departing Sun, 30 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Sun, 30 Aug, arriving in Chicago Midway.Price includes taxes and charges.From P15,393, select.

      Find the cheapest month to fly from Raleigh / Durham to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Raleigh / Durham to Chicago Midway flights are currently cheapest in October.
      Aug
      from P11,108
      Sep
      from P5,841
      Oct
      from P5,323
      Nov
      from P6,902
      Dec
      from P7,188
      Jan
      from P10,692
      Feb
      from P8,231
      Mar
      from P11,928
      Apr
      Find prices
      May
      Find prices
      Jun
      Find prices
      Jul
      from P10,684

      Direct flights from Raleigh / Durham to Chicago Midway

      Southwest Airlines

      Raleigh / Durham to Chicago Midway: Alternative routes

      Compare routes from Raleigh / Durham 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
      ClosestCheapest
      from P5,323
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      from P5,804
      Search flights

      Chicago Rockford

      127km from central Chicago
      from P7,324
      Search flights

      Durham to Chicago: Flight information

      The things to know before you go.
      Cheapest flight foundP5,323
      Cheapest month to flyOctober
      Average flight time2 hrs
      Most popular airlineSouthwest Airlines
      Average flights per week19

      Finding cheap flights from Raleigh / Durham to Chicago Midway: Frequently asked questions

      The best price we found for a return flight from Raleigh / Durham to Chicago Midway is P11,571. 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 is the average flight time from Raleigh / Durham to Chicago Midway.
      Southwest Airlines flies direct from Raleigh / Durham to Chicago Midway.
      As of August 2026, there are 19 flights per week flying from Raleigh / Durham to Chicago Midway.
      The cheapest month to fly from Raleigh / Durham to Chicago Midway is usually September.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Raleigh / Durham Airport to Chicago Midway Airport on Saturday, 12 September 2026.
      Yes – the average flight time is 2 hours.
      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 and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

      Travelling from Raleigh / Durham Airport (RDU) to Chicago Midway Airport (MDW): what you need to know

      • The average length of a direct flight from Raleigh / Durham Airport to Chicago Midway Airport is 1 hour 55 minutes.

      • Chicago is one hour behind Durham and is in the UTC-6 timezone.

      • You can choose from 11 weekly Raleigh / Durham Airport to Chicago Midway Airport flights. The 05:30 departure with Southwest Airlines is the earliest available. Southwest Airlines operates the last service of the day at 21:00.

      • Get to the airport on time so you don't miss your RDU to MDW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid a last-minute sprint to the gate.

      • Travelling during a peak time like July? Public holidays and other popular seasons can result in longer queues at airport checkpoints. Play things extra safe and arrive up to four hours before international flights and two hours before domestic departures.

      • Southwest Airlines is your ticket to exploring Chicago (and perhaps some other exciting parts of the United States!). Check out the direct flights from Raleigh / Durham Airport to Chicago Midway Airport offered by this popular carrier.

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

      • Southwest Airlines ranks as the leading on-time carrier for RDU to MDW flights, with 82.28% of its services arriving on schedule.

      • Consider adding a stopover when booking your ticket from Raleigh / Durham Airport to Chicago Midway Airport. Just uncheck 'Direct flights only' to break up your trip, or visit a new city along the way. Check out these options between RDU and MDW:

        • Detroit Wayne County Airport

        • Port Columbus Airport

        • Cincinnati Northern Kentucky Airport

      Handy information about Raleigh / Durham Airport (RDU)

      Arriving at Chicago Midway Airport (MDW)

      • If you're coming in on a late Raleigh / Durham Airport to Chicago Midway Airport flight, few things beat the convenience of staying close to the terminal. Grab your luggage from the carousel and then be resting not long after at one of these hotels near MDW:

      • Travel at your own pace with a Chicago Midway Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and discover more of Chicago and beyond.

      • Secure the lowest price by reserving your vehicle from Chicago Midway Airport about four weeks ahead of your trip.

      Getting from Chicago Midway Airport (MDW) to central Chicago

      • You'll find MDW at 5700 South Cicero.

      • From Chicago Midway Airport, Chicago is approximately 16 kilometers away. It takes around 25 minutes to get to the centre driving.

      • Getting there on public transport typically takes 30 minutes.

      When to fly to Chicago Midway Airport (MDW)

      • It's time to work out your dates for your flight from Raleigh / Durham Airport to Chicago Midway Airport. July is the busiest month to visit Chicago. If you like a quieter vibe, go in December.

      • Lock in your flight from Raleigh / Durham Airport to Chicago Midway Airport for July if you'd like to visit Chicago during its warmest month. You can expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

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

      Explore more of the United States

      • Columbus is just one of the many cities in the United States waiting to be discovered once you've seen the sights of Chicago. Around 451 kilometers away to the south-east, well-known attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • If there's time to check out another great destination in the United States, head for Indianapolis, roughly 257 kilometers south-east of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among its highlights.

      Plan the rest of your trip from Durham to Chicago

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