Cheap flights from Raleigh to Chicago from $129
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Raleigh to Chicago departing on 10/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Not ready to book? to track prices.Southwest flights from Raleigh to Chicago Midway Airport
Our best Southwest deals on Raleigh to Chicago Midway Airport flight tickets
Frontier flights from Raleigh to Chicago Midway Airport
Our best Frontier deals on Raleigh to Chicago Midway Airport flight tickets
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Fly from
Fly to
Route
Depart
Return
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Thu 10/22
1:16 pm-5:45 pm
1 stop5h 29m
Chicago Midway
Sun 10/25
6:24 am-12:21 pm
1 stop4h 57m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 11/24
5:25 am-12:00 pm
2 stops7h 35m
Chicago Midway
Tue 12/1
6:00 am-12:05 pm
1 stop5h 05m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Thu 2/11
5:35 am-8:30 am
1 stop3h 55m
Chicago Midway
Tue 2/16
12:55 pm-8:15 pm
2 stops6h 20m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Fri 11/20
8:46 pm-1:45 pm
1 stop17h 59m
Chicago Midway
Sun 11/22
9:09 am-12:27 am
1 stop14h 18m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Thu 12/3
11:30 am-7:30 pm
2 stops9h 00m
Chicago Midway
Mon 12/7
1:15 pm-4:05 pm
Nonstop1h 50m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Tue 10/20
4:20 pm-11:43 pm
1 stop8h 23m
Chicago Midway
Mon 10/26
6:15 am-12:21 pm
1 stop5h 06m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Wed 11/4
9:30 pm-5:47 pm
2 stops21h 17m
Chicago Midway
Fri 11/6
6:08 am-12:03 pm
1 stop4h 55m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 10/26
5:20 am-9:32 am
1 stop5h 12m
Chicago Midway
Thu 11/5
6:44 pm-11:41 pm
1 stop3h 57m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 10/26
5:20 am-9:32 am
1 stop5h 12m
Chicago Midway
Mon 11/2
6:04 am-11:40 am
1 stop4h 36m
RaleighChicago
RDU Raleigh-Durham - MDW Chicago Midway
RDUMDW
Raleigh-Durham
Mon 10/26
12:59 pm-6:00 pm
1 stop6h 01m
Chicago Midway
Mon 11/2
6:44 pm-11:41 pm
1 stop3h 57m
See travel insights to Chicago from
How to get the cheapest flight ticket from Raleigh to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Raleigh and Chicago Midway Airport?
Prices are currently typical for flights on this route.
Typical prices usually range from $235 to $385.The lowest price recently found on this route was $257.
What is the cheapest month to fly to Chicago Midway Airport?
The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Raleigh, with most prices found around $262. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Raleigh during the month October is also very affordable. Most momondo users find prices during this month for around $287.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Raleigh. The lowest ticket price found for a Wednesday departure recently was $373. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Raleigh because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $499.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Raleigh in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $352 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $433. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Raleigh-Durham to Chicago Midway flight route?
Fly from Raleigh-Durham to Chicago Midway for the best Raleigh-Durham - Chicago Midway flight prices
How far in advance should I book a flight from Raleigh to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Raleigh when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $397 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Raleigh for as low as $289 on momondo.
What cabin class options are available on Raleigh to Chicago Midway Airport flights?
There is only 1 cabin class available to choose from on Raleigh to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Raleigh to Chicago Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Raleigh to Chicago Midway Airport.
How have Raleigh to Chicago Midway Airport flight prices changed over time?
What is the cheapest airline that flies from Raleigh-Durham to Chicago Midway?
Southwest is the most popular carrier operating from Raleigh-Durham to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Raleigh according to our data. Southwest is the first choice among our users, with 77% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Raleigh to Chicago Midway Airport on average per day?
As of October 2026, 1 flights take off from Raleigh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 6:00AM, with 36% of daily flights taking off at noon.
How many flights depart from Raleigh to Chicago Midway Airport on average per week?
As of October 2026, 13 flights take off from Raleigh and land in Chicago Midway Airport each week. The most common flight departure day for this route is Mon, with 23% of weekly flights taking off on this day.
When to book flights from Raleigh to Chicago Midway Airport
Cheap Raleigh to Chicago Midway Airport (RDU to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Raleigh to Chicago Midway Airport
Frequently asked questions about flying from Raleigh to Chicago Midway Airport
How far is Raleigh-Durham to Chicago Midway by plane?
The distance between Raleigh-Durham and Chicago Midway is about 641.7 mi. Flights usually cover this in 1h 55m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Raleigh-Durham Airport to Chicago Midway Airport?
Prices for flights from Raleigh-Durham Airport to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Raleigh-Durham Airport to Chicago Midway Airport?
The number of operators available for flights from Raleigh-Durham Airport to Chicago Midway Airport is 3 as of October 2026.
How old do you have to be to fly from Raleigh-Durham Airport to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Raleigh-Durham Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Raleigh to Chicago Midway Airport?
Based on momondo bookings for flights between Raleigh and Chicago Midway Airport, the leading plane model is Airbus A319, making up 15.18% of the total bookings. Other popular models include Boeing 737-800 with 15.05%, Boeing 737 MAX 8 with 13.04%, and Embraer 175 with 10.18%.
What is the most popular airline from Raleigh to Chicago Midway Airport?
Based on momondo bookings for flights between Raleigh and Chicago Midway Airport, the leading airline is Southwest, making up 85% of the total bookings. Other popular airlines include Frontier with 11% and JetBlue with 4%.
Best airlines flying from Raleigh to Chicago Midway Airport
Compare and see reviews for airlines that fly from Raleigh to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $156 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $224 | Free Cancellation | Rating 7.1 3,048 reviews | |||
| PriceFrom $233 | Free Cancellation | Rating 7.9 4,224 reviews |
Southwest Flights From Raleigh to Chicago Midway Airport
Southwest operates around 13 flights from Raleigh to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $366, but momondo users have found Southwest deals from Raleigh to Chicago Midway Airport from as low as $233 round-trip. Southwest has been scored 7.9/10 in 4,224 reviews.
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Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Raleigh to Chicago?
It is quick and easy to find Raleigh to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Raleigh to Chicago with flexible booking policies on momondo?
All flight searches from Raleigh to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Raleigh to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Raleigh.
I’m not ready to book a flight from Raleigh to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Raleigh are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.