S$ 29 Cheap Flights from Orlando to Chicago (ORL-CHI)

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Cheap Flights from Orlando to Chicago starting at S$ 29

Book one-way or return flights from Orlando to Chicago from as little as S$ 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 lowest average weekly prices of the corresponding route on Trip.com.

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 S$ 45

Delta Air Lines

From S$ 112

Sun Country Airlines

From S$ 118

Frontier Airlines

From S$ 132

Southwest Airlines

From S$ 132

Allegiant Air

From S$ 148

Jetblue Airways

From S$ 202

Silver Airways

From S$ 206

American Airlines

From S$ 318

United Airlines

From S$ 359

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
S$ 49
MCO
21:39
3h 4m
Direct
ORD
23:43
Orlando International Airport - O'Hare International Airport
Wed, May 1Frontier Airlines
S$ 132
SFB
06:30
2h 43m
Direct
RFD
08:13
Orlando Sanford International Airport - Chicago Rockford International Airport
Mon, May 6Allegiant Air
S$ 148
SFB
06:30
2h 43m
Direct
RFD
08:13
Orlando Sanford International Airport - Chicago Rockford International Airport
Mon, May 6Allegiant Air
S$ 148
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Frequently Asked Questions

When to buy 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 is a flight from Orlando (ORL) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around S$ 280.
How long is a flight from Orlando (ORL) to Chicago (CHI)?
It takes about 3 hours 26 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 time does the earliest flight from Orlando to Chicago depart?
The earliest flight departs from Orlando (MCO) at 06:55 and arrives in Chicago (ORD) at 09:00.
What time does the latest flight from Orlando to Chicago depart?
The latest flight departs from Orlando (MCO) at 18:26 and arrives in Chicago (ORD) at 20:30.
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?
There are 5 airports near Chicago: O'Hare International Airport, Chicago Du Page County Airport, Midway 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 from Orlando to Chicago

Cheapest direct flight price	S$ 28
Cheapest return ticket price	S$ 62
Cheapest month	April
Peak season for travel	October
Flight distance	1,588.53km
Average flight time	3 hours 26 minutes
Popular airline	American Airlines