Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customise 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 Orlando Airport to Chicago
Cheap return flights
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
JetBlue flights from Orlando Airport to Chicago
Our best JetBlue deals on Orlando Airport to Chicago flight tickets
Sun Country Air flights from Orlando Airport to Chicago
Our best Sun Country Air deals on Orlando Airport to Chicago flight tickets
See travel insights to Chicago from
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 cheapest month to fly to Chicago from Orlando Airport is in February. Flight prices, which tend to average around £109, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Chicago from Orlando Airport during April instead. Flights to Chicago in April, while not as cheap as those in February, still average around £109.
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 Wednesday when prices can be found for as low as £213. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £494.
What is the cheapest time of day to depart on your flight to Chicago?
Flying to Chicago from Orlando Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as £295 when looking at flights departing in the evening. Flights in the afternoon are often more expensive, with an average ticket price of £539.
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 3 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £161 when searching 3 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 £142 on momondo.
What cabin class options are available on Orlando to Chicago flights?
There are 2 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.
How many flights depart from Orlando Airport to Chicago on average per day?
As of February 2025, there are 45 flights per day flying from Orlando Airport to Chicago. The most common time of day flights depart is 14:00, with 56% of flights taking off in the afternoon.
How many flights depart from Orlando Airport to Chicago on average per week?
The number of flights available between Orlando Airport and Chicago is 321 per week as of February 2025. The most frequent departure day is Thu, with 17% of weekly flights leaving 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?
Chicago is 993.7 mi away from Orlando. In terms of flight time, this usually takes a little over 3h 00m.
When did momondo last update prices for flights from Orlando Airport to Chicago?
Prices for flights from Orlando Airport to Chicago refresh daily.
How old do you have to be to fly from Orlando Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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 flights between Orlando Airport and Chicago, the leading plane model is Airbus A320neo, making up 16.93% of the total bookings. Other popular models include Airbus A321neo with 16.10%, Airbus A321-100/200 with 10.12%, and Boeing 737-800 with 10.01%.
Why use momondo?
Why should I use momondo to find a flight deal from Orlando to Chicago?
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 Orlando to Chicago for you.
Can I find flights from Orlando to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Orlando with this policy.
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.