Cheap Flights from Orlando to Chicago from CAD 29️ 2024

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Find Orlando to Chicago flights starting at CAD 29.

Book one-way or return flights from Orlando to Chicago from as little as CAD 29. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Orlando to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Orlando to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Orlando to Chicago

View airlines operating flights from Orlando to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines

From CAD 45

Delta Air Lines

From CAD 112

Sun Country Airlines

From CAD 119

Frontier Airlines

From CAD 132

Southwest Airlines

From CAD 133

Allegiant Air

From CAD 149

Jetblue Airways

From CAD 202

Silver Airways

From CAD 207

United Airlines

From CAD 360

American Airlines

From CAD 388

ANA airlines

Find more flights and airlines

Alternative Routes for Orlando to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Orlando to Chicago.

Cheapest
MCO
05:01
2h 53m
Direct
MDW
06:54
Orlando International Airport - Midway International Airport
Wed, May 22Frontier Airlines
CAD 50
MCO
21:39
3h 4m
Direct
ORD
23:43
Orlando International Airport - O'Hare International Airport
Wed, May 1Frontier Airlines
CAD 132
SFB
06:30
2h 43m
Direct
RFD
08:13
Orlando Sanford International Airport - Chicago Rockford International Airport
Mon, May 6Allegiant Air
CAD 149
SFB
06:30
2h 43m
Direct
RFD
08:13
Orlando Sanford International Airport - Chicago Rockford International Airport
Mon, May 6Allegiant Air
CAD 149
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How do I find the cheapest flights?

When are flight tickets from Orlando (ORL) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Orlando to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Orlando (ORL) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around CAD 287.
How long is the flight from Orlando (ORL) to Chicago (CHI)?
It takes about 3 hours 27 minutes to fly from Orlando (ORL) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Orlando (ORL) to Chicago (CHI)?
Airlines with flights from Orlando (ORL) to Chicago (CHI): Volaris, Southwest Airlines, Frontier Airlines, American Airlines, Iberia and United Airlines.
What's the most popular airline for direct flights from Orlando (ORL) to Chicago (CHI)?
Spirit Airlines operates 6 direct flights from Orlando (ORL) to Chicago (CHI).
How many airports in Chicago (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from Orlando to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Orlando to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information for Orlando to Chicago Flights

Cheapest direct flight price	CAD 28
Cheapest return ticket price	CAD 62
Cheapest month	April
Peak season for travel	October
Flight distance	1,588.53km
Average flight time	3 hours 27 minutes
Popular airline	American Airlines