Cheap flights from Chicago to Orlando from $35
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 to Orlando departing on 6/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Orlando
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Frontier flights from Chicago to Orlando
Our best Frontier deals on Chicago to Orlando flight tickets
Delta flights from Chicago to Orlando
Our best Delta deals on Chicago to Orlando flight tickets
See travel insights to Orlando from
How to get the cheapest flight ticket from Chicago 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 typical price of a round-trip flight between Chicago and Orlando?
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, with most prices found around $184. If you’re not able to fly to Orlando in September, then August is your next best option. Flight prices from Chicago to Orlando during August average around $194.
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 $266. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $314.
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 $240. In contrast, the most expensive time of day to depart to Orlando is in the morning when prices are around $309.
What is the cheapest Chicago to Orlando flight route?
Fly from Chicago Midway to Orlando for the best Chicago - 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 when booking 4 weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around $294 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 for as low as $240 on momondo.
What cabin class options are available on Chicago to Orlando flights?
There are 4 cabin classes available to choose from on Chicago to Orlando 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 Chicago to Orlando?
Allegiant Air, Spirit Airlines, and Frontier are the most popular carriers operating from Chicago to Orlando
What airlines fly to Orlando?
United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Orlando from Chicago according to our data. United Airlines is the first choice among our users, with 29% of people opting to fly with this airline when traveling to Orlando. Keep in mind that there are 7 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 to Orlando on average per day?
As of May 2025, there are 53 flights per day flying from Chicago to Orlando. The most common time of day flights depart is 2:00PM, with 44% of flights taking off at noon.
How many flights depart from Chicago to Orlando on average per week?
As of May 2025, 372 flights take off from Chicago and land in Orlando each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.
When to book flights from Chicago to Orlando
Cheap Chicago to Orlando (CHI to ORL) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Orlando
How far is Chicago to Orlando by plane?
The straight-line distance from Chicago to Orlando is 985.3 mi. A reasonable flight in good conditions will take 2h 30m.
When did momondo last update prices for flights from Chicago to Orlando?
Prices for flights from Chicago to Orlando refresh daily.
How many operators does momondo search for flights from Chicago to Orlando?
As of May 2025, there are 7 operators available to choose from for flights from Chicago to Orlando.
How old do you have to be to fly from Chicago 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 to Orlando.
What documentation or ID do you need to fly to Orlando?
The travel and health documents required for your trip to Orlando 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 Orlando. 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 Chicago to Orlando?
Based on momondo bookings for flights between Chicago and Orlando, the leading plane model is Airbus A321neo, making up 19.58% of the total bookings. Other popular models include Airbus A320neo with 16.76%, Boeing 737-800 with 11.34%, and Airbus A321-100/200 with 8.27%.
What is the most popular airline from Chicago to Orlando?
momondo data reveals that the most frequently booked airline on the route from Chicago to Orlando is Frontier, representing 44% of all bookings. The subsequent popular airlines are American Airlines at 20%, Spirit Airlines at 15%, and United Airlines at 12%.
Best airlines flying from Chicago to Orlando
Compare and see reviews for airlines that fly from Chicago to Orlando with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $72 | Free Cancellation | Rating 5.9 3,286 reviews | |||
| PriceFrom $88 | Free Cancellation | Rating 6.3 8,005 reviews | |||
| PriceFrom $119 | Free Cancellation | Rating 7.3 731 reviews | |||
| PriceFrom $179 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $193 | Free Cancellation | Rating 7.4 8,744 reviews | |||
| PriceFrom $196 | Free Cancellation | Rating 8.0 7,951 reviews | |||
| PriceFrom $217 | Free Cancellation | Rating 8.0 4,290 reviews |
Southwest Flights From Chicago to Orlando
Southwest flight deals from Chicago to Orlando start from $217 round-trip. Over the 66 Southwest flights for this route in a normal week, average airfare is usually $396 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Chicago to Orlando
United Airlines (7.4/10 from 8,744 reviews) operates around 34 flights from Chicago to Orlando in any given week. The average United Airlines airfare for this route is around $364, with deals from around $193 rare but found on momondo. Referenced prices are for round-trip Chicago to Orlando flight searches in the last 72 hours.
Traveling to a place near Orlando?
Book flights to Orlando if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Orlando?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Orlando. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Orlando with flexible booking policies on momondo?
Yes. All flights to Orlando from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Chicago to Orlando?
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 Orlando from Chicago.
I’m not ready to book a flight from Chicago to Orlando right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Orlando from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.