US$20️ Cheap Flights from Orlando to Chicago (2024)

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Orlando to Chicago - Flights Starting at US$20

Book one-way or return flights from Orlando to Chicago from as little as US$20. 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.

We've found these cheap flights for you. You may book a one-way or round trip as per your needs.

We monitor flight fares to help you seize the best deals effortlessly

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

Cheapest airlines flights 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 US$20

Delta Air Lines

From US$82

United Airlines

From US$82

Sun Country Airlines

From US$87

Frontier Airlines

From US$97

Southwest Airlines

From US$97

Allegiant Air

From US$109

American Airlines

From US$142

Jetblue Airways

From US$148

Silver Airways

From US$152

ANA airlines

Find more flights and airlines

Alternative Routes from Orlando to Chicago

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
US$31
MCO
21:39
3h 4m
Direct
ORD
23:43
Orlando International Airport - O'Hare International Airport
Wed, May 1Frontier Airlines
US$97
SFB
06:30
2h 43m
Direct
RFD
08:13
Orlando Sanford International Airport - Chicago Rockford International Airport
Mon, May 6Allegiant Air
US$109
SFB
06:30
2h 43m
Direct
RFD
08:13
Orlando Sanford International Airport - Chicago Rockford International Airport
Mon, May 6Allegiant Air
US$109
Find More Flights

Frequently Asked Questions

When are flight tickets from Orlando (ORL) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Orlando to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Orlando (ORL) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $205.
How long does it take to fly from Orlando (ORL) to Chicago (CHI) and what is the distance?
It takes around 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. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
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.

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

Orlando to Chicago Flight Information

Cheapest nonstop flight price	$19
Cheapest round-trip ticket price	$45
Off-season for travel	April
Peak season for travel	October
Flight distance	1,588.53km
Average flight time	3 hours 27 minutes
Popular airline	American Airlines