Cheap flights from Orlando to Chicago from $58
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Orlando to Chicago departing on 8/1. 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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Frontier flights from Orlando to Chicago Midway Airport
Our best Frontier deals on Orlando to Chicago Midway Airport flight tickets
Delta flights from Orlando to Chicago Midway Airport
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How to get the cheapest flight ticket from Orlando 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando, with most prices found around $94. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Orlando during the month February is also very affordable. Most momondo users find prices during this month for around $165.
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 Orlando. The lowest ticket price found for a Friday departure recently was $161. 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, Tuesday is the most expensive day to depart from Orlando because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $272.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Orlando at noon is the least expensive time of day to depart. momondo users have found prices as low as $175 when looking at flights departing at noon. Try not to purchase tickets in the evening because they tend to be around $225. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Orlando to Chicago Midway flight route?
Fly from Orlando to Chicago Midway for the best Orlando - 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 Orlando when booking 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $194 when searching 23 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Orlando for as low as $81 on momondo.
What cabin class options are available on Orlando to Chicago Midway flights?
There are 1 cabin classes available to choose from on Orlando 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 Orlando to Chicago Midway?
Frontier, Southwest, and Delta are the most popular carriers operating from Orlando to Chicago Midway
What airlines fly to Chicago Midway Airport?
Frontier, Southwest and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Orlando according to our data. Frontier is the first choice among our users, with 71% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 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 Orlando to Chicago Midway Airport on average per day?
As of April 2025, 6 flights take off from Orlando and land in Chicago Midway Airport each day. The most common flight departure time for this route is 2:00PM, with 40% of daily flights taking off in the afternoon.
How many flights depart from Orlando to Chicago Midway Airport on average per week?
As of April 2025, 42 flights take off from Orlando and land in Chicago Midway Airport each week. The most common flight departure day for this route is Tue, with 21% of weekly flights taking off on this day.
When to book flights from Orlando to Chicago Midway Airport
Cheap Orlando to Chicago Midway Airport (ORL to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago Midway Airport
How far is Orlando to Chicago Midway by plane?
The distance between Orlando and Chicago Midway is about 982.0 mi. Typically, this will take 2h 45m by plane in normal conditions.
When did momondo last update prices for flights from Orlando to Chicago Midway Airport?
Prices for flights from Orlando to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Orlando to Chicago Midway Airport?
As of April 2025, there are 3 operators available to choose from for flights from Orlando to Chicago Midway Airport.
How old do you have to be to fly from Orlando to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Orlando to Chicago Midway Airport?
Based on momondo bookings for flights between Orlando and Chicago Midway Airport, the leading plane model is Airbus A320neo, making up 19.80% of the total bookings. Other popular models include Airbus A321neo with 16.74%, Boeing 737 MAX 8 with 12.77%, and Boeing 737-800 Passenger/BBJ2 (winglets) with 10.89%.
What is the most popular airline from Orlando to Chicago Midway Airport?
Based on momondo bookings for flights between Orlando and Chicago Midway Airport, the leading airline is Frontier, making up 69% of the total bookings. Other popular airlines include Southwest with 31%.
Best airlines flying from Orlando to Chicago Midway Airport
Compare and see reviews for airlines that fly from Orlando to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $74 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $184 | Free Cancellation | Rating 8.0 4,295 reviews | |||
| PriceFrom $227 | Free Cancellation | Rating 8.0 7,929 reviews |
Southwest Flights From Orlando to Chicago Midway Airport
Southwest operates around 61 flights from Orlando to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $375, but momondo users have found Southwest deals from Orlando to Chicago Midway Airport from as low as $184 round-trip. Southwest has been scored 8.0/10 in 4,295 reviews.
Frontier Flights From Orlando to Chicago Midway Airport
Another popular option for Orlando to Chicago Midway Airport flights is Frontier (5.9/10, 3,287 ratings). Frontier flies from Orlando to Chicago Midway Airport around 1 time per week, with deals starting from $74 round-trip and rising to an average price of around $149.
Traveling to a place near Chicago?
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 Orlando to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Orlando.
Can I find flights from Orlando to Chicago with flexible booking policies on momondo?
Flights from Orlando to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Orlando to Chicago?
Once all potential Orlando to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Orlando to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.