Cheap flights from Orlando to Chicago from €637

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ORL-CHI
2552 kmmulti-stop
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CHI-ORL
2552 kmmulti-stop
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How to get the cheapest flight ticket from Orlando 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 is in September. Flight prices, which tend to average around €114, are often lower during this time because this is during the off-season. If you don’t want to visit Chicago in September, then you should wait until August to fly from Orlando, when ticket prices are also cheap, with an average price of €136.

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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around €187 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Orlando for as low as €156 on momondo.

What cabin class options are available on Orlando to Chicago flights?

There are 1 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 have Orlando to Chicago flight prices changed over time?

As of July 2025, prices for Orlando to Chicago flights are approximately 16% cheaper when compared to flights at the same time last year.

When to book flights from Orlando to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Orlando to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Orlando to Chicago (ORL to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Orlando to Chicago

Direct flights

None
There are no direct flights from Orlando to Chicago. There are no popular flight routes from Orlando to Chicago.

  • How far is Orlando to Chicago by plane?

    The straight-line distance from Orlando to Chicago is 1585.7 km.

  • When did momondo last update prices for flights from Orlando to Chicago?

    Prices for flights from Orlando to Chicago were last updated today.

  • How old do you have to be to fly from Orlando 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 stopovers. It is recommended that you verify with the airline you are booking with for travel from Orlando to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's licence and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Orlando to Chicago?


Why 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?

momondo does allow users to show only those flights to Chicago from Orlando which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Orlando to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Orlando to Chicago.

I’m not ready to book a flight from Orlando to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Orlando and alert you when they change.


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