Cheap flights from Orlando Airport to Chicago from $42
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 7/2. 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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Spirit Airlines flights from Orlando Airport to Chicago
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Frontier flights from Orlando Airport to Chicago
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How to get the cheapest flight ticket from Orlando Airport to Chicago
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?
The month of September is, on average, the cheapest month to fly to Chicago from Orlando Airport, with most prices found around $140. If you’re not able to fly to Chicago in September, then February is your next best option. Flight prices from Orlando Airport to Chicago during February average around $152.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $237. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Orlando Airport to Chicago for around $449.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Orlando Airport to Chicago during this time can be as low as $193. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $654.
What is the cheapest Orlando to Chicago flight route?
Fly from Orlando to Chicago Midway for the best Orlando - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Orlando Airport when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $223 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando Airport for as low as $187 on momondo.
What cabin class options are available on Orlando to Chicago flights?
There are 4 cabin classes available to choose from on Orlando to Chicago 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?
Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from Orlando to Chicago
What airlines fly to Chicago?
Frontier, American Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Orlando Airport according to our data. Frontier is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Orlando Airport to Chicago on average per day?
57 flights are operational daily from Orlando Airport to Chicago as of June 2025. The most popular departure time for this route is 2:00PM, with 50% of flights per day taking off in the afternoon.
How many flights depart from Orlando Airport to Chicago on average per week?
405 flights are operational weekly from Orlando Airport to Chicago as of June 2025. The most popular departure day for this route is Thu, with 19% of flights per week taking off on this day.
When to book flights from Orlando Airport to Chicago
Cheap Orlando Airport to Chicago (MCO to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Orlando Airport to Chicago
How far is Orlando to Chicago by plane?
There are 993.7 mi between Orlando and Chicago. A reasonable flight in good conditions will take 2h 45m.
When did momondo last update prices for flights from Orlando Airport to Chicago?
Prices for flights from Orlando Airport to Chicago refresh daily.
How many operators does momondo search for flights from Orlando Airport to Chicago?
As of June 2025, there are 6 operators available to choose from for flights from Orlando Airport to Chicago.
How old do you have to be to fly from Orlando Airport to Chicago?
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.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Orlando Airport to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Orlando Airport to Chicago is Airbus A321neo (20.74% of total bookings). The next most popular plane models are Airbus A320neo (14.10%), Boeing 737 MAX 8 (10.15%), and Boeing 737-800 (9.97%).
What is the most popular airline from Orlando Airport to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Orlando Airport to Chicago is Frontier (48% of total bookings). The next most popular airlines are American Airlines (18%), Spirit Airlines (15%), and United Airlines (10%).
Best airlines flying from Orlando Airport to Chicago
Compare and see reviews for airlines that fly from Orlando Airport to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $66 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $72 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $158 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $181 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,950 reviews |
Southwest Flights From Orlando Airport to Chicago
Across 70 Southwest flights from Orlando Airport to Chicago this week, the average price was $338, with the best Southwest deals starting from $181 round-trip. 4,287 users have rated Southwest on momondo, with an average score of 8.0/10.
United Airlines Flights From Orlando Airport to Chicago
Another popular option for Orlando Airport to Chicago flights is United Airlines (7.4/10, 8,790 ratings). United Airlines flies from Orlando Airport to Chicago around 33 times per week, with deals starting from $157 round-trip and rising to an average price of around $329.
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?
Finding the right flight to Chicago from Orlando is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Orlando to Chicago with flexible booking policies on momondo?
All flight searches from Orlando to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Orlando to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Orlando. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
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.