Cheap Flight Tickets from Chicago (CHI) to Orlando (ORL), Starting at $248

Good to Know: Cheapest and Fastest CHI - ORL Flights

Useful information for finding best airline tickets from Chicago All Airport to Orlando All Airport on your next trip.

Cheapest Round Trip Flight

$446

WN Southwest Airlines • nonstop • 3h 55m

Nov 22 – Nov 26

The cheapest round trip flight from Chicago to Orlando (CHI-ORL-CHI) is currently $446

🔍 Search Flights

Cheapest Direct Flight

$260

AA American Airlines • nonstop • 4h 10m

Nov 02

The cheapest nonstop flight from Chicago to Orlando (CHI-ORL) is currently $260

🔍 Search Flights

Fastest Flight

3h 55m

The fastest nonstop flight from Chicago to Orlando (CHI-ORL) takes 3h 55m

Top Airlines Flying from Chicago to Orlando

Southwest Airlines-WN

Southwest Airlines

Avelo Airlines (XP)

Avelo Airlines

Sun Country Airlines (SY)

Sun Country Airlines

American Airlines, AA

American Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Alaska Airlines -AS

Alaska Airlines

Latest Flight Deals from Chicago (CHI) to Orlando (ORL)

Compare and book low fare round-trip air tickets from Chicago to Orlando. Ideal for travelers with confirmed return itineraries.

Nov 22 - Nov 26, Economy
WN
Chicago → Orlando
3h 55m
5:10 AM - 8:45 AM • nonstop
WN
Chicago → Orlando
7h 5m
8:25 AM - 11:50 AM • nonstop
$446
Southwest Airlines
Nov 22 - Nov 26, Economy
WN
Chicago → Orlando
4h
8:40 PM - 12:20 AM • nonstop
WN
Chicago → Orlando
7h 5m
7:30 AM - 10:55 AM • 1 stop
$451
Southwest Airlines
Nov 22 - Nov 26, Economy
WN
Chicago → Orlando
7h 35m
8:00 AM - 1:55 PM • 1 stop
WN
Chicago → Orlando
4h 10m
11:20 AM - 1:10 PM • nonstop
$451
Southwest Airlines
Nov 22 - Nov 26, Economy
WN
Chicago → Orlando
10h 20m
7:50 AM - 3:10 PM • nonstop
WN
Chicago → Orlando
4h 10m
11:20 AM - 1:10 PM • nonstop
$451
Southwest Airlines
Nov 22 - Nov 26, Economy
SY
Chicago → Orlando
27h 10m
7:35 PM - 1:05 PM • 1 stop
XP
Chicago → Orlando
12h 34m
11:14 AM - 6:08 PM • 1 stop
$493
Sun Country Airlines
Nov 22 - Nov 26, Economy
SY
Chicago → Orlando
9h 14m
11:40 AM - 6:34 PM • 1 stop
XP
Chicago → Orlando
12h 34m
11:14 AM - 6:08 PM • 1 stop
$589
Sun Country Airlines

Fly from Chicago to Orlando with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Orlando? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Chicago to Orlando Flights

What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from CHI to ORL?
The most popular airline flying from Chicago to Orlando are
Can I fly from CHI to ORL non-stop?
Yes, you can fly CHI to ORL non-stop on
Which airlines fly nonstop between Chicago and Orlando?
The non-stop flights between Chicago and Orlando are .
What’s the earliest departure time from CHI to ORL Airport?
The earliest flight leaves CHI at 5:10 am and lands in ORL - Orlando All Airport
What are the airports in Orlando?
ORL
Can I make changes to my Chicago to Orlando flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from CHI to ORL?
Read the fare rules of the Chicago to Orlando air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Orlando?
operate flights between Chicago and Orlando
How long does a flight from Chicago to Orlando take?
It takes approximately 3 hour to fly non-stop from CHI to ORL, which is 997.02 miles by air.
Which airlines provide the cheapest flights from Chicago (CHI) to Orlando (ORL) ?
In the past couple of days, the cheapest tickets to ORL from CHI were found on SY : USD 493
Do I need a passport to fly between CHI and ORL?
No
What’s the latest departure time from CHI to ORL ?
The last flight leaves CHI at 8:40 pm

Chicago (CHI) to Orlando (ORL): Airport Information

Origin Airport Chicago All Airport, Chicago, US
Destination Airport Orlando All Airport, Orlando, US
Distance 997 miles

More Flight Options for Chicago (CHI) and Orlando (ORL)

Why Fareleaders for CHI to ORL Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Chicago to Orlando flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on CHI to ORL flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Chicago to Orlando flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Chicago (CHI) to Orlando (ORL)
Terms and Conditions*