Book Cheap Flight Tickets from Chicago (CHI) to Orlando (ORL)
Relish through our astounding low fares and hit the city which is renowned as “O Town”

Crystal Travel is the best platform to book your flight at the lowest fares. We get affordable prices after matching different fares through multiple airlines. Just enter your travel details including the departure and arrival destinations and book the next cheap flights from Chicago to Orlando right away before the fares fluctuate. Get assistance from our travel expert for the booking process or any other queries.

About Chicago

One of the biggest cities in the US is Chicago, which is located in Illinois on Lake Michigan. Its skyline is highlighted by skyscrapers like the landmark John Hancock Center, the 1,451-foot Willis Tower (originally the Sears Tower), and the neo-Gothic Tribune Tower, which is renowned for its daring construction. Additionally, the city is well known for its museums, particularly the Art Institute of Chicago, which is home to notable Impressionist and Post-Impressionist pieces.

About Orlando

Orlando is the ideal vacation spot for everyone, whether they are traveling as a family, a couple, a single person, or a group of friends. This is because of Orlando's amazing diversity, which guarantees each visitor a fantastic trip filled with different experiences. In other words, there is never a shortage of things to do in Orlando, and while you're there, you'll create lifelong treasured experiences. For instance, if you enjoy a good adrenaline rush, you'll love our huge water parks, open-air theme parks, and incredible attractions. You still have a lot to learn, including what to eat, where to shop, how to experience ecotourism and other things you shouldn't miss.
Cheap Flights from Chicago to Orlando

Click on the nearest Origin Airport of your choice to unlock various flight deals

FAQs on Chicago to Orlando Flights
1. Which airlines fly directly from Chicago to Orlando?

Chicago Midway International Airport (MDW) and Chicago O'Hare International Airport (ORD) are the two airports for direct flights. Whereas in Orlando, only Orlando International Airport (MCO) flies directly. 

The airlines that serve from MDW to MCO directly are Southwest whereas the airlines that serve directly from ORD to MCO are Spirit, Frontier, United, Southwest, and American.

2. I’m booking a non-stop/direct flight to Orlando from Chicago. Which airport do I choose?

Chicago Midway International Airport (MDW) and Chicago O'Hare International Airport (ORD) at a distance of 12 and 18 miles respectively from the center of Chicago. You can take a direct flight from any of the two airports. 

In Orlando, there are two airports that are nearest to the city—Orlando International Airport (MCO)(13 miles) and Orlando Sanford International Airport (SFB) (27 miles) but you can only land directly in Orlando through MCO.

3. What is the duration of the flight between Chicago and Orlando?
There are flights of varying duration depending upon routes and airlines. The minimum duration is around 2 hours and 30 minutes to fly from Chicago to Orlando.
4. Which airline has the least delayed flights from CHI to ORL?
The airline that is least delayed with a success rate of 88.4% is Delta airlines. After that American and United are the two airlines to reach on time. However, the delay of the flight is unconditional and can occur at any time due to certain reasons. You will be informed beforehand when a flight is delayed.
5. Which is the cheapest day of the week to fly from Chicago to Orlando?
The cheapest days to fly are Tuesdays, Wednesdays, and Saturdays. The rest of the days are high on pricing. So to book a low-fare flight from Chicago to Orlando keep these days in mind. If you have a flexible schedule you can even have a return ticket on Tuesdays, Wednesdays, and Saturdays.
6. Do I need to pay any fees or charges for canceling my flight from CHI to ORL?
Some airlines have dropped the cancellation fees since the pandemic wave, while others still do. Therefore, it is best to obtain accurate information from the relevant airlines through their customer service team or by reading their website policies.
7. Do airlines offer sleeping areas to passengers traveling from Chicago to ORL?
In MDW there are no dedicated sleeping zones, you can search nearby hotels to sleep or compromise by lying on the floor. Bring a traveler’s mattress to have a comfortable sleep. In ORD, there are no sleeping zones, there is very less sleep-friendly furniture, and you will have to lay on the floor so bring your mattress or book access to the first class lounge to have a comfortable sleep.
8. Am I allowed to carry food/eatables on my flight to ORL?
You can bring dry and solid food with you, but if it is liquid or gel-like, there will be an issue. In order to achieve a clear image scanned by the X-ray equipment, TSA inspectors would urge you to separate the solid and dry goods that can cause a backlog while getting the images scanned.
9. What is the baggage allowance on a flight from CHI to ORL?

The baggage allowance depends upon aircraft size, cabin type, and the kind of airline you travel with. You are allowed to carry one piece of checked-in baggage and one piece of carry-on while traveling by air as per the standards of IATA. 

For checked baggage, there is a limit of 32 KGS at maximum and the lower weight you can carry is 23KGS. The dimension for the same is 158 cm or 62 inches. 

Whereas for the carry-on baggage there is 8KGS or 18LBS that is permitted. The dimensions are 22inches(long) , 18inches(wide) , and 10inches (high). If added, it should be 50 inches in total. 

It is preferable that you check the website of the respective airline or ask the customer support team.

10. I lost my baggage during my flight to Orlando from Chicago. How can I recover it?
If you have lost your luggage, it is the duty of the relevant airlines to locate it using their built-in tracking system and ensure that it arrives at the baggage claim area without incident. All you have to do is lodge a complaint against the mishandled luggage in the lost and found zone. The lost luggage can be claimed within 30 days.
11. How would I get the best deal on my flight from CHI to ORL?
Simply enter your travel information, including the airports and dates of departure and arrival. You will unlock plenty of options. Choose the one with the best routes and prices available. With just a few quick and simple clicks, you can easily book a low-cost flight from CHI to ORL. Visit our social media accounts on Instagram, Twitter, and Facebook to get the finest and most popular discounts, or sign up for our newsletters. To receive the best coupons and bargains ever, you may also get assistance from our travel specialists.
Search Offers Navigation
Get a great deal on your next holiday
mail