Find the cheapest flights on Expedia from Orlando (MCO) to Chicago (CHI). Flight ticket prices change frequently based on availability and demand. We send price-drop alerts to make air travel simple and flexible. The lowest one-way fare found on Expedia for this route in the past 7 days starts at £88 for travel on 23 January 2027.
Cheap Flights from Orlando to Chicago (MCO-CHI)
Prices were available within the past 7 days and start at £88 for one-way flights and £166 for return, for the period specified. Prices and availability are subject to change.
Find the cheapest month to fly from Orlando (MCO) to Chicago (CHI)
December is typically the cheapest month to flyDecember is typically the cheapest month to fly
From £91 - £205 per traveller.
Book with confidence
Compare flights from Orlando to Chicago easily and book with confidence
For travelling on business or for pleasure, Expedia makes it easy to book your flights from Orlando to Chicago. Operating between them flights per day, 6 airlines cover the route. And fly direct, getting you to CHI-All Airports in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Orlando Intl. to CHI-All Airports.
To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights.
Grab a great deal on your flight from Orlando Intl. (MCO) to CHI-All Airports (CHI)
The easiest way to view the best deals on flights from Orlando to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Orlando Intl. to CHI-All Airports start at just £166 and range up to £481.
To find an even better deal, try
being flexible on your dates – midweek flights can be cheaper
looking for other airports near Orlando and Chicago
booking your flight during December, the cheapest month on this route
varying your flight times – early morning and late at night are sometimes cheaper
Why you should book your Orlando to Chicago flight with Expedia!
We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Orlando Intl. to CHI-All Airports for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.
Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.
Frequently Asked Questions
How much is a flight from Orlando Intl. Airport to Chicago, IL (CHI-All Airports)?
Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip flights between MCO and Chicago, IL (CHI-All Airports) start from £166. Book today to secure the best price for your trip. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from MCO to Chicago, IL (CHI-All Airports)?
This varies between airlines, as each has its own set of terms and conditions. Head to the Customer Service Portal, where there are simple instructions on how to cancel your flight online.
How do I find cheap flights from MCO to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for MCO to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Orlando Intl. Airport (MCO) to Chicago, IL (CHI-All Airports)?
The flight distance between Orlando Intl. Airport (MCO) and Chicago, IL (CHI-All Airports) (CHI) is 1,650 kilometres. Listen to your favourite tunes or get stuck into a book and the journey will whiz by.
Which airlines fly direct from Orlando Intl. Airport (MCO) to Chicago, IL (CHI-All Airports)?
It's easy to fly directly from MCO to Chicago, IL (CHI-All Airports). Below are some of the most popular carriers that offer nonstop services on this route:
Southwest Airlines - (WN) with 247 monthly flights
United Airlines - (UA) with 173 monthly flights
American Airlines - (AA) with 121 monthly flights
Frontier Airlines - (F9) with 82 monthly flights
Are Orlando Intl. Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Airline tickets from Orlando Intl. Airport to Chicago, IL (CHI-All Airports) are available up to a year before departure on Expedia. And although you may occasionally nab a fantastic last-minute deal, it's never a sure thing. Also, booking your flights ahead of time means you'll have more options — and you can avoid ending up with the dreaded middle seat! We regularly update our fares to bring you the biggest bargains, so check back often for all the latest specials.