Cheap flights from Chicago Midway Airport to Orlando from $79
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Orlando departing on 8/20. 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 Chicago Midway Airport to Orlando
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Delta flights from Chicago Midway Airport to Orlando
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How to get the cheapest flight ticket from Chicago Midway Airport to Orlando
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 Orlando?
The month of September is, on average, the cheapest month to fly to Orlando from Chicago Midway Airport, with most prices found around $173. If you’re not able to fly to Orlando in September, then August is your next best option. Flight prices from Chicago Midway Airport to Orlando during August average around $189.
What is the cheapest day to depart on your flight to Orlando?
Our data shows that Tuesday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $263. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $318.
What is the cheapest time of day to depart on your flight to Orlando?
The cheapest time of day to fly to Orlando is in the afternoon when flights can be purchased for as low as $244. In contrast, the most expensive time of day to depart to Orlando is in the morning when prices are around $307.
What is the cheapest Chicago Midway to Orlando flight route?
Fly from Chicago Midway to Orlando for the best Chicago Midway - Orlando flight prices
How far in advance should I book a flight to Orlando?
You are more likely to see cheaper flights to Orlando from Chicago Midway Airport when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around $308 when searching 4 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando from Chicago Midway Airport for as low as $228 on momondo.
What cabin class options are available on Chicago Midway to Orlando flights?
There are 1 cabin classes available to choose from on Chicago Midway to Orlando 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 Chicago Midway Airport to Orlando flights?
You could potentially save up to 8% on your flight if you consider stops on a Chicago Midway Airport to Orlando flight.
How have Chicago Midway Airport to Orlando flight prices changed over time?
As of June 2025, prices for Chicago Midway Airport to Orlando flights are approximately 113% more expensive when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago Midway to Orlando?
Southwest, Frontier, and Allegiant Air are the most popular carriers operating from Chicago Midway to Orlando
What airlines fly to Orlando?
Frontier, Southwest and Delta are the top three most popular airlines that fly to Orlando from Chicago Midway Airport according to our data. Frontier is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Orlando. Keep in mind that there are 5 different airlines that fly to Orlando on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago Midway Airport to Orlando on average per day?
As of June 2025, there are 8 flights per day flying from Chicago Midway Airport to Orlando. The most common time of day flights depart is 9:00AM, with 40% of flights taking off at noon.
How many flights depart from Chicago Midway Airport to Orlando on average per week?
As of June 2025, there are 56 flights per week flying from Chicago Midway Airport to Orlando. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.
When to book flights from Chicago Midway Airport to Orlando
Cheap Chicago Midway Airport to Orlando (MDW to ORL) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Orlando
How far is Chicago Midway to Orlando by plane?
Orlando is 982.0 mi away from Chicago Midway. Flights usually cover this in 2h 30m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to Orlando?
Prices for flights from Chicago Midway Airport to Orlando are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Orlando?
As of June 2025, there are 5 operators available to choose from for flights from Chicago Midway Airport to Orlando.
How old do you have to be to fly from Chicago Midway Airport to Orlando?
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 Chicago Midway Airport to Orlando.
What documentation or ID do you need to fly to Orlando?
The necessary travel and health documents for your Orlando trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to Orlando?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Orlando is Airbus A320neo (17.52% of total bookings). The next most popular plane models are Airbus A321neo (15.48%), Boeing 737 MAX 8 (12.46%), and Boeing 737-800 Passenger/BBJ2 (winglets) (10.61%).
What is the most popular airline from Chicago Midway Airport to Orlando?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to Orlando is Frontier, representing 59% of all bookings. The subsequent popular airlines are Southwest at 38% and Spirit Airlines at 2%.
Best airlines flying from Chicago Midway Airport to Orlando
Compare and see reviews for airlines that fly from Chicago Midway Airport to Orlando with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $93 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $101 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $232 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $248 | Free Cancellation | Rating 7.4 8,790 reviews |
Southwest Flights From Chicago Midway Airport to Orlando
Across 51 Southwest flights from Chicago Midway Airport to Orlando this week, the average price was $398, with the best Southwest deals starting from $232 round-trip. 4,287 users have rated Southwest on momondo, with an average score of 8.0/10.
Frontier Flights From Chicago Midway Airport to Orlando
Frontier (5.9/10 from 3,295 reviews) operates around 5 flights from Chicago Midway Airport to Orlando in any given week. The average Frontier airfare for this route is around $215, with deals from around $101 rare but found on momondo. Referenced prices are for round-trip Chicago Midway Airport to Orlando flight searches in the last 72 hours.
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Why should I use momondo to find a flight deal from Chicago to Orlando?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Orlando for you.
Can I find flights from Chicago to Orlando with flexible booking policies on momondo?
All flight searches from Chicago to Orlando on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Orlando?
momondo provides multiple filters to help you find the best flight to Orlando from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to Orlando right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Orlando, momondo offers a useful price alert feature which will track prices for flights to Orlando from Chicago and alert you when they change.