Cheap Flights from Raleigh / Durham to Chicago Midway from $271

Compare Raleigh / Durham to Chicago Midway flight deals

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

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Flight deals from Raleigh / Durham Airport to Chicago Midway Airport

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 $271. Find the lowest prices on one-way and return tickets right here.

Chicago.$271 per passenger.Departing Wed, 29 Apr, returning Mon, 4 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Wed, 29 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 4 May, arriving in Raleigh / Durham.Price includes taxes and charges.From $271, select.

Chicago.$271 per passenger.Departing Fri, 1 May, returning Sun, 3 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Fri, 1 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 3 May, arriving in Raleigh / Durham.Price includes taxes and charges.From $271, select.

Chicago.$271 per passenger.Departing Mon, 13 Apr, returning Tue, 14 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Mon, 13 Apr, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 14 Apr, arriving in Raleigh / Durham.Price includes taxes and charges.From $271, select.

Chicago.$276 per passenger.Departing Sat, 2 May, returning Sat, 2 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Sat, 2 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 2 May, arriving in Raleigh / Durham.Price includes taxes and charges.From $276, select.

Chicago.$305 per passenger.Departing Sat, 11 Apr, returning Wed, 15 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Sat, 11 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 15 Apr, arriving in Raleigh / Durham.Price includes taxes and charges.From $305, select.

Chicago.$330 per passenger.Departing Mon, 30 Mar, returning Tue, 31 Mar.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Mon, 30 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 31 Mar, arriving in Raleigh / Durham.Price includes taxes and charges.From $330, select.

Chicago.$334 per passenger.Departing Wed, 29 Apr, returning Mon, 4 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Wed, 29 Apr, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 4 May, arriving in Raleigh / Durham.Price includes taxes and charges.From $334, select.

Chicago.$343 per passenger.Departing Sat, 30 May, returning Mon, 1 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Sat, 30 May, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 1 Jun, arriving in Raleigh / Durham.Price includes taxes and charges.From $343, select.

Chicago.$380 per passenger.Departing Mon, 30 Mar, returning Thu, 2 Apr.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Raleigh / Durham on Mon, 30 Mar, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Thu, 2 Apr, arriving in Raleigh / Durham.Price includes taxes and charges.From $380, select.

Chicago.$403 per passenger.Departing Mon, 1 Jun, returning Mon, 1 Jun.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Raleigh / Durham on Mon, 1 Jun, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 1 Jun, arriving in Raleigh / Durham.Price includes taxes and charges.From $403, select.

Chicago.$441 per passenger.Departing Sat, 30 May, returning Mon, 1 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Sat, 30 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 1 Jun, arriving in Raleigh / Durham.Price includes taxes and charges.From $441, select.

Chicago.$503 per passenger.Departing Fri, 17 Jul, returning Mon, 20 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Fri, 17 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 20 Jul, arriving in Raleigh / Durham.Price includes taxes and charges.From $503, select.

Chicago.$503 per passenger.Departing Tue, 23 Jun, returning Tue, 7 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Tue, 23 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 7 Jul, arriving in Raleigh / Durham.Price includes taxes and charges.From $503, select.

Chicago.$503 per passenger.Departing Thu, 10 Sep, returning Mon, 14 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Thu, 10 Sep, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 14 Sep, arriving in Raleigh / Durham.Price includes taxes and charges.From $503, select.

Chicago.$503 per passenger.Departing Wed, 24 Jun, returning Tue, 30 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Wed, 24 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 30 Jun, arriving in Raleigh / Durham.Price includes taxes and charges.From $503, select.

Chicago.$503 per passenger.Departing Fri, 31 Jul, returning Tue, 4 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Raleigh / Durham on Fri, 31 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 4 Aug, arriving in Raleigh / Durham.Price includes taxes and charges.From $503, 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 April.

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Direct flights from Raleigh / Durham to Chicago Midway

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.

Durham to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$271
Cheapest month to fly	April
Average flight time	1 hr, 58 mins
Most popular airline	Southwest Airlines
Average flights per week	21

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

How much are return flights from Raleigh / Durham to Chicago Midway?

The best price we found for a return flight from Raleigh / Durham to Chicago Midway is $271. 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 Raleigh / Durham to Chicago Midway?

1 hour and 58 minutes is the average flight time from Raleigh / Durham to Chicago Midway.

Which airlines fly direct from Raleigh / Durham to Chicago Midway?

Southwest Airlines flies direct from Raleigh / Durham to Chicago Midway.

How many flights are there a week from Raleigh / Durham to Chicago Midway?

As of March 2026, there are 21 flights per week flying from Raleigh / Durham to Chicago Midway.

When is the cheapest time to fly from Raleigh / Durham to Chicago Midway?

The cheapest month to fly from Raleigh / Durham to Chicago Midway is usually April.

Which upcoming date is cheapest to fly from Raleigh / Durham Airport to Chicago Midway Airport on?

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 Monday, 13 April 2026.

Can I get a direct flight from Raleigh / Durham Airport to Chicago Midway Airport?

Yes – the average flight time is 1 hour and 58 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.

Which is the cheapest airline to fly from Raleigh / Durham Airport to Chicago Midway with?

Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

Flying from Raleigh-Durham International Airport (RDU) to Chicago Midway International Airport (MDW): what you need to know

Hop on a direct flight from Raleigh-Durham International Airport to Chicago Midway International Airport and you'll be travelling for an average of 2 hours.
The timezone in Chicago is UTC-5, which is one hour behind Durham.
You can choose from 19 weekly Raleigh-Durham International Airport to Chicago Midway International Airport flights. The 05:30 departure with Southwest Airlines is the earliest available. Frontier Airlines operates the latest service of the day at 22:00.
To ensure you get on your RDU to MDW flight, leave enough time to check in and drop off your luggage. Turning up two hours before international departures and one hour before domestic flights is the standard rule.
Travelling during a peak time such as July? School holidays and other high seasons can mean longer lines at airport checkpoints. Play things extra safe and get there up to four hours ahead of an international flight and two hours before a domestic departure.
Frontier Airlines offers direct flights from Raleigh-Durham International Airport to Chicago Midway International Airport. Book with this popular airline, then get ready to check out the sights in Chicago — and maybe even more of United States if your schedule allows.
Frontier Airlines is the airline most travellers choose to fly with on this route.
Southwest Airlines is the most punctual carrier operating RDU to MDW flights. An impressive 80.47% of its departures on this route land on time.
Think about adding a stopover when booking your ticket from Raleigh-Durham International Airport to Chicago Midway International Airport. Simply uncheck 'Direct flights only' to break up your trip, or enjoy a detour to a new and interesting place. Check out these options between RDU and MDW:
- John Glenn Columbus International Airport
- Cincinnati/Northern Kentucky Airport
- Detroit Metropolitan Wayne County Airport

How to find the cheapest flights from Raleigh-Durham International Airport (RDU) to Chicago Midway International Airport (MDW)

$135 is the best price for a one-way Raleigh-Durham International Airport to Chicago Midway International Airport flight. Return flights start at $271. These prices can change depending on availability and demand.
Book six months before flying. After crunching the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from RDU to MDW.
May is the cheapest month for flights from Raleigh-Durham International Airport to Chicago Midway International Airport. If you're looking to fly during a different time of year, the 'Whole month' tool will give you the lowest airfares for every month.
Spend less time searching for cheap flights from RDU to MDW by setting up a Price Alert. You'll get an email or notification through the app when a lower fare pops up.
Tailor your flights using filters. Choose your ideal arrival and departure times, airlines and total journey duration. You can also sort results by 'Fastest,' 'Cheapest' or 'Best' flights from Raleigh-Durham International Airport to Chicago Midway International Airport.

Handy information about Raleigh-Durham International Airport (RDU)

80.09% of flights leaving Raleigh-Durham International Airport arrive at their destination on schedule. Given its strong performance rating, you're unlikely to experience delays when flying out of RDU.
Raleigh-Durham International Airport is around 23 kilometres from central Durham. If you're ride-sharing, catching a cab or driving from the centre, it'll take you 20 minutes or so to arrive, depending on the traffic.
The journey on public transport typically takes 1 hour 10 minutes.
Get your trip off to a relaxed start by staying near RDU. Whether you're catching an early flight from Raleigh-Durham International Airport to Chicago Midway International Airport or just don't want to be rushed, these stays are the answer:

Arriving at Chicago Midway International Airport (MDW)

The last thing you need is a long trip to your hotel if you're landing late on a Raleigh-Durham International Airport to Chicago Midway International Airport flight. Check in to one of these accommodation options near MDW instead:
Pick up a Chicago Midway International Airport rental car and explore Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are well-known companies to choose from here.
For the best deal, reserve your vehicle from Chicago Midway International Airport about four weeks before travelling.

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

You'll find MDW at 5700 South Cicero.
From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre driving.
If you're travelling on public transport, expect a journey time of around 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

It's time to choose your trip dates for your flight from Raleigh-Durham International Airport to Chicago Midway International Airport. July is the most popular month to head to Chicago. If you prefer a more low-key vibe, go in May.
The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Book your flights from Raleigh-Durham International Airport to Chicago Midway International Airport in this month if this is the type of weather you enjoy.
Search for cheap tickets from RDU to MDW in January if you like travelling in cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

Explore more of United States

Chicago is easy to fall in love with, but there are so many other parts of United States waiting to be explored. Around 451 kilometres south-east of Chicago, a visit to Columbus will fill your itinerary to the brim. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Indianapolis is another standout destination in United States and is around 257 kilometres south-east of Chicago. No journey is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.