RDU - MDW

$114 Find Cheap Flights from Raleigh to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$239
Typical prices: $261-$394
Frontier
Mon 10/8Thu 10/11
RDU - MDW • 1 stop
Cheapest non-stop
$257
Typical prices: $277-$401
Southwest
Mon 11/5Wed 11/7
RDU - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 00m
Direct flights
+1
Direct flights
+1
When to book
7 weeks
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 47% compared to booking last minute.
Insights
Insights
When to travel
October
Cheapest • 26% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston George Bush Intcntl (IAH)
Cheapest • Avg $162 (round-trip)
Detroit Metropolitan Wayne County (DTW)
Shortest trip • 3h 49m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Raleigh to Midway (RDU-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Raleigh to Midway

Sun, Sep 27 - Thu, Oct 8
Frontier Logo
1:56 pm - 11:44 pmRDU  Raleigh-Durham-MDW Chicago Midway
10h 48m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:21 am - 12:28 pmMDW  Chicago Midway-RDU Raleigh-Durham
5h 07m1 stop Atlanta Hartsfield-Jackson
$239Frontier
Mon, Sep 28 - Wed, Oct 7
Frontier Logo
1:56 pm - 5:51 pmRDU  Raleigh-Durham-MDW Chicago Midway
4h 55m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 12:38 pmMDW  Chicago Midway-RDU Raleigh-Durham
5h 13m1 stop Atlanta Hartsfield-Jackson
$239Frontier
Mon, Sep 28 - Tue, Oct 6
Frontier Logo
1:56 pm - 11:44 pmRDU  Raleigh-Durham-MDW Chicago Midway
10h 48m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 12:38 pmMDW  Chicago Midway-RDU Raleigh-Durham
5h 13m1 stop Atlanta Hartsfield-Jackson
$239Frontier
Thu, Oct 1 - Mon, Oct 5
Frontier Logo
6:35 am - 5:46 pmRDU  Raleigh-Durham-MDW Chicago Midway
12h 11m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:50 am - 12:38 pmMDW  Chicago Midway-RDU Raleigh-Durham
4h 48m1 stop Atlanta Hartsfield-Jackson
$239Frontier
Sat, Oct 17 - Tue, Oct 20
Southwest Logo
5:05 pm - 6:00 pmRDU  Raleigh-Durham-MDW Chicago Midway
1h 55mnonstop
Southwest Logo
7:40 am - 12:50 pmMDW  Chicago Midway-RDU Raleigh-Durham
4h 10m1 stop Nashville Intl
$249Southwest
Sat, Oct 3 - Tue, Oct 6
Multiple Airlines Logo
9:46 pm - 5:46 pmRDU  Raleigh-Durham-MDW Chicago Midway
21h 00m2 stops Tampa Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:25 am - 12:38 pmMDW  Chicago Midway-RDU Raleigh-Durham
5h 13m1 stop Atlanta Hartsfield-Jackson
$255Multiple Airlines
Sat, Oct 3 - Wed, Oct 7
Southwest Logo
8:20 am - 9:20 amRDU  Raleigh-Durham-MDW Chicago Midway
2h 00mnonstop
Southwest Logo
7:55 am - 10:55 amMDW  Chicago Midway-RDU Raleigh-Durham
2h 00mnonstop
$257Southwest
Wed, Feb 3 - Sat, Feb 6
Southwest Logo
5:30 pm - 6:35 pmRDU  Raleigh-Durham-MDW Chicago Midway
2h 05mnonstop
Southwest Logo
3:45 pm - 6:30 pmMDW  Chicago Midway-RDU Raleigh-Durham
1h 45mnonstop
$257Southwest
Sat, Oct 10 - Sat, Oct 17
Delta Logo
5:20 am - 9:32 amRDU  Raleigh-Durham-MDW Chicago Midway
5h 12m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 4:01 pmMDW  Chicago Midway-RDU Raleigh-Durham
5h 32m1 stop Detroit Metropolitan Wayne County
$277Delta
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
9:46 pm - 5:51 pmRDU  Raleigh-Durham-MDW Chicago Midway
21h 05m2 stops Orlando Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:46 pm - 12:29 amMDW  Chicago Midway-RDU Raleigh-Durham
4h 43m1 stop Atlanta Hartsfield-Jackson
$277Multiple Airlines
Booking Insights

Price, demand and travel trends for Raleigh to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Raleigh to Chicago Midway Airport with more confidence.

How much is a round-trip flight from Raleigh to Chicago Midway Airport?

Round-trip flights from Raleigh to Chicago Midway Airport start at $239. Prices are below average for this route right now, with typical round-trip fares ranging from $261 to $394. The lowest price found in the past 5 days was $239 on Frontier.

What's the cheapest day of the week to fly from Raleigh to Chicago Midway Airport?

Wednesday is the cheapest day of the week to fly from Raleigh to Chicago Midway Airport, it is 9% cheaper than the average day. Sunday is the most expensive day with flight prices 13% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Raleigh to Chicago Midway Airport?

  • October is the cheapest month to fly from Raleigh to Chicago Midway Airport at $235 round-trip.
  • July ($371) and June ($365) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 57% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Raleigh to Chicago Midway Airport the cheapest?

Flights from Raleigh to Chicago Midway Airport are cheapest 7 weeks before departure. Booking in this window typically costs about 47% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals
Expert advice

Expert advice for your flight from Raleigh to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Jessica Macdonald

Jessica Macdonald

Expert on RDU

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more

Key details for Raleigh to Chicago Midway Airport flights

Low season

January

Cheapest flight

$114
Best time to beat the crowds with an average 18% drop in price.
Flight from Raleigh to Chicago Midway Airport

When to book flights from Raleigh to Midway

Are your dates flexible? Find out the best times to travel from Raleigh to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Raleigh to Chicago Midway Airport flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Raleigh to Chicago Midway Airport flights?

    Among airlines operating Raleigh to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Raleigh to Chicago Midway Airport?

    Only Southwest operates flights between Raleigh and Chicago Midway Airport.

  • Which airports can I use when flying from Raleigh to Chicago Midway Airport?

    Flights from Raleigh to Chicago Midway Airport usually depart from Raleigh-Durham (RDU) and arrive at Chicago Midway (MDW).

  • Which airlines include bags at no extra cost on Raleigh to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Raleigh to Chicago Midway Airport?

    Only Economy Class is available on flights from Raleigh to Chicago Midway Airport.

  • How much can I save by taking a layover when flying from Raleigh to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $162 round-trip via Houston George Bush Intcntl (IAH), compared to $330 for nonstop.

  • What is the standard checked-bag allowance on flights from Raleigh to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Raleigh to Chicago Midway Airport?

    The Airbus A319 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737-800 variants.

  • Which airports do connecting flights from Raleigh to Chicago Midway Airport pass through?

    One-stop flights from Raleigh to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 92% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 7% of one-stop connections
    • Houston George Bush Intcntl (IAH) - 2% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Raleigh to Chicago Midway Airport?

    Yes. Being flexible with your travel dates can save you up to 20% on the Raleigh to Chicago Midway Airport route. Wednesday is the cheapest departure day at $291 round-trip on average, while Sunday is the most expensive at $361, a difference of $70. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Raleigh to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Raleigh to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • What are the earliest and latest flights from Raleigh to Chicago Midway Airport?

    These are the earliest and latest flight times available from Raleigh to Chicago Midway Airport:

    • Earliest: departs at 6:55 am and lands at 8:55 am
    • Latest: departs at 8:55 pm and lands at 10:55 pm.

    The flight takes about 2h 00m.

  • How expensive are last-minute Raleigh to Chicago Midway Airport flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 54% above the route average of $318. Book 7 weeks before departure for the lowest fares.

  • How long is a flight from Raleigh to Chicago Midway Airport?

    A nonstop flight from Raleigh to Chicago Midway Airport takes 2h 00m, covering 631 miles.

  • Do I need a passport to fly from Raleigh to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Raleigh to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $239 to $1,500. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Raleigh to Chicago Midway Airport looking right now?

    One-way fares from Raleigh to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $120, which is 30% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Raleigh to Chicago Midway Airport?

    Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 3h 49m, compared with 7h 31m via Atlanta Hartsfield-Jackson (ATL) and 24h 14m via Houston George Bush Intcntl (IAH).

  • What is the time difference between Raleigh and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Raleigh (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • How much should I expect to pay for a Raleigh to Chicago Midway Airport flight?

    Round-trip flights from Raleigh to Chicago Midway Airport range from $261 to $394, with an average of $318 over the past 12 months. Anything below $261 counts as a good deal.

  • Which airlines offer Wi-Fi on Raleigh to Chicago Midway Airport flights?

    JetBlue is the only airline on the Raleigh to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Raleigh to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $291 - about $70 less than Sunday (19% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 7 weeks before you fly. On this route, that window historically saves about 47% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Raleigh to Chicago Midway Airport trip for October. Fares historically average $235 round-trip in that month - typically $136 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Houston George Bush Intcntl Airport (IAH) can be cheaper than flying direct. The cheapest layover option averages $162 round-trip on this route - about $168 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

Prefer to fly direct from Raleigh to Chicago Midway Airport?

 
Find which airlines fly direct from Raleigh-Durham Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Raleigh-Durham to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Raleigh-Durham

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Raleigh to Midway

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago