Cheap flights from Raleigh to Chicago from $53
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 8/22. 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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Delta flights from Raleigh to Chicago Midway Airport
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Frontier flights from Raleigh to Chicago Midway Airport
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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 cheapest month to fly to Chicago Midway Airport?
The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Raleigh, with most prices found around $224. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Raleigh during the month October is also very affordable. Most momondo users find prices during this month for around $234.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Raleigh. The lowest ticket price found for a Friday departure recently was $317. 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 $402.
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 evening is the least expensive time of day to depart. momondo users have found prices as low as $275 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $376. 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 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 $287 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 $113 on momondo.
What cabin class options are available on Raleigh-Durham to Chicago Midway flights?
There are 1 cabin classes available to choose from on Raleigh-Durham to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Raleigh-Durham to Chicago Midway?
Frontier, Southwest, and Delta are the most popular carriers 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 57% 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 July 2025, 2 flights take off from Raleigh and land in Chicago Midway Airport each day. The most common flight departure time for this route is 3:00PM, with 42% of daily flights taking off in the afternoon.
How many flights depart from Raleigh to Chicago Midway Airport on average per week?
As of July 2025, 17 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 24% 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
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 4 as of July 2025.
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 Boeing 737 MAX 8, making up 18.11% of the total bookings. Other popular models include Boeing 737-800 with 15.04%, Embraer 175 with 11.80%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 11.54%.
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 66% of the total bookings. Other popular airlines include Frontier with 23%, Delta with 8%, and United Airlines with 3%.
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 $62 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 8.0 7,983 reviews | |||
| PriceFrom $170 | Free Cancellation | Rating 8.0 4,270 reviews | |||
| PriceFrom $197 | Free Cancellation | Rating 7.4 8,861 reviews |
Southwest Flights From Raleigh to Chicago Midway Airport
Southwest operates around 17 flights from Raleigh to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $314, but momondo users have found Southwest deals from Raleigh to Chicago Midway Airport from as low as $170 round-trip. Southwest has been scored 8.0/10 in 4,270 reviews.
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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.