Cheap flights from Orlando Airport 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 Airport 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 Airport to Chicago Midway Airport
Our best Frontier deals on Orlando Airport to Chicago Midway Airport flight tickets
Delta flights from Orlando Airport to Chicago Midway Airport
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How to get the cheapest flight ticket from Orlando Airport 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 February is, on average, the cheapest month to fly to Chicago Midway Airport from Orlando Airport, with most prices found around $87. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Orlando Airport during the month September is also very affordable. Most momondo users find prices during this month for around $167.
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 Airport. 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 Airport 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 Airport 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 Airport 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 Airport 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 Airport 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 Airport to Chicago Midway Airport on average per day?
6 flights are operational daily from Orlando Airport to Chicago Midway Airport as of April 2025. The most popular departure time for this route is 2:00PM, with 40% of flights per day taking off in the afternoon.
How many flights depart from Orlando Airport to Chicago Midway Airport on average per week?
42 flights are operational weekly from Orlando Airport to Chicago Midway Airport as of April 2025. The most popular departure day for this route is Tue, with 21% of flights per week taking off on this day.
When to book flights from Orlando Airport to Chicago Midway Airport
Cheap Orlando Airport to Chicago Midway Airport (MCO to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Orlando Airport to Chicago Midway Airport
How far is Orlando to Chicago Midway by plane?
The distance between Orlando and Chicago Midway is about 990.5 mi. 2h 45m is a normal flight duration for this route.
When did momondo last update prices for flights from Orlando Airport to Chicago Midway Airport?
Prices for flights from Orlando Airport to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Orlando Airport to Chicago Midway Airport?
There are 3 operators available for flights from Orlando Airport to Chicago Midway Airport as of April 2025.
How old do you have to be to fly from Orlando Airport 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 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 Orlando Airport to Chicago Midway Airport?
Based on momondo bookings for flights between Orlando Airport 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 Airport to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Orlando Airport to Chicago Midway Airport is Frontier, representing 71% of all bookings. The subsequent popular airlines are Southwest at 26% and Delta at 3%.
Best airlines flying from Orlando Airport to Chicago Midway Airport
Compare and see reviews for airlines that fly from Orlando Airport to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $78 | Free Cancellation | Rating 5.9 3,287 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 Airport to Chicago Midway Airport
The lowest priced Southwest flight from Orlando Airport to Chicago Midway Airport from the last 72 hours was $184. Generally, Southwest has 42 flights on this route every week with an average price of $375. Southwest is rated 8.0/10 by our users.
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Why should I use momondo to find a flight deal from Orlando to Chicago?
It is quick and easy to find Orlando 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 Orlando to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Orlando on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Orlando to Chicago?
Once you have performed a search for Orlando to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Orlando 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.