Cheap Flights from Orlando (ORL) to Chicago (ORD)

Popular airlines from Orlando Executive Airport (ORL) to Chicago O'Hare Intl. Airport (ORD)

Find the cheapest month to fly from Orlando (ORL) to Chicago (ORD)

February is typically the cheapest month to fly

From $70 - $298 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $112
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $112
Flights from Orlando (ORL) to Chicago (ORD)
Origin airport
Orlando Executive
Destination airport
O'Hare Intl.
Distance
998 mi

Orlando to Chicago Flights

The cheapest times to fly from Orlando to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Orlando to Chicago are during the month of . You can find some of the cheapest flights from Orlando to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Orlando to Chicago

Sunday is one of the best days to book for cheap flights from Orlando to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Orlando to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Orlando to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Orlando to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Orlando to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD) cost?
Lock in a cheap one-way flight or cheap return flight from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD)?
Planning your trip for is a great way to save, as it's the cheapest month for flights between ORL and ORD. You'll typically find the lowest prices during off-peak months.
Which airlines fly direct from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD)?
There are no direct routes from Orlando, FL (ORL-Orlando Executive) to O'Hare Intl. Airport (ORD). However, you can find other airports that offer nonstop flights. Start your journey at Orlando Intl. Airport (MCO) and fly straight to Chicago without layovers.
What is the cheapest airline that flies from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll fly you from ORL to ORD. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
How many flights per day from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD)?
Nonstop flights from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your travel dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORL to ORD?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD)?
To touch down at O'Hare Intl. Airport (ORD) on schedule, select a flight that leaves from Orlando Executive Airport (ORL) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until just before your trip to book a ticket from ORL to ORD often results in higher prices. Although you may find some last-minute deals, they're not always guaranteed. Allow some flexibility in your schedule for a better chance of getting a bargain.
Is it cheaper to book an ORL to ORD flight and hotel package?
Opting for an ORL to ORD flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Select from our extensive range of accommodations and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Orlando Executive Airport (ORL) to O'Hare Intl. Airport (ORD)?
It's generally possible to reschedule or cancel your ORL to ORD flight. However, if it's been more than 24 hours since booking, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find further details on our Customer Service portal.

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*Available to One Key members.