£38 Find Cheap Flights from Chicago to Florida

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Florida departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Florida

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Florida Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Florida that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Florida

Sat, 6 Dec - Wed, 10 Dec
Spirit Airlines Logo
15:26 - 19:45ORD-FLL
3h 19mdirect
Spirit Airlines Logo
12:14 - 21:48FLL-ORD
10h 34m1 stop
£75Spirit Airlines
Find Deal
Thu, 11 Dec - Mon, 15 Dec
Spirit Airlines Logo
05:00 - 09:10ORD-FLL
3h 10mdirect
Spirit Airlines Logo
21:45 - 00:09FLL-ORD
3h 24mdirect
£76Spirit Airlines
Find Deal
Sat, 6 Dec - Tue, 9 Dec
United Airlines Logo
10:50 - 14:59ORD-FLL
3h 09mdirect
United Airlines Logo
16:13 - 18:40FLL-ORD
3h 27mdirect
£99United Airlines
Find Deal
Sat, 14 Feb - Sat, 28 Feb
Southwest Logo
16:25 - 20:10ORD-MCO
2h 45mdirect
Southwest Logo
09:05 - 11:10MCO-ORD
3h 05mdirect
£104Southwest
Find Deal
Fri, 14 Nov - Mon, 17 Nov
Frontier Logo
11:53 - 00:54ORD-MIA
12h 01m1 stop
Frontier Logo
19:07 - 00:11MIA-ORD
6h 04m1 stop
£109Frontier
Find Deal
Sat, 14 Feb - Sat, 21 Feb
Southwest Logo
16:25 - 20:10ORD-MCO
2h 45mdirect
Southwest Logo
07:20 - 12:15MCO-ORD
5h 55m1 stop
£112Southwest
Find Deal
Tue, 16 Dec - Tue, 16 Dec
United Airlines Logo
10:55 - 15:10ORD-MIA
3h 15mdirect
United Airlines Logo
16:16 - 18:45MIA-ORD
3h 29mdirect
£115United Airlines
Find Deal
Fri, 14 Nov - Mon, 17 Nov
Frontier Logo
08:26 - 19:15ORD-MIA
9h 49m1 stop
Frontier Logo
19:07 - 00:11MIA-ORD
6h 04m1 stop
£147Frontier
Find Deal
Fri, 14 Nov - Mon, 17 Nov
American Airlines Logo
16:40 - 20:50ORD-MIA
3h 10mdirect
American Airlines Logo
22:07 - 00:37MIA-ORD
3h 30mdirect
£203American Airlines
Find Deal
Sun, 30 Nov - Wed, 3 Dec
American Airlines Logo
00:48 - 04:35ORD-MCO
2h 47mdirect
American Airlines Logo
08:15 - 10:29MCO-ORD
3h 14mdirect
£245American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Florida flights

Get data-powered insights and trends into flights from Chicago to Florida to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Florida flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Florida from Chicago found in the last 72 hours was to West Palm Beach, at £22 return. The most popular route is from Chicago O'Hare Intl Airport (ORD) to West Palm Beach (PBI), and the cheapest round-trip airline ticket found on this route in the last 72 hours was £22.

Can I save money by flying with a stopover from Chicago to Florida?

The average return price for all direct flights, flights with one stopover, and flights with two stopovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a stopover may cost you more time, but you can also save money on the route, with a 1 stop stopover the cheapest option at £153 on average.

What is the cheapest month to fly from Chicago to Florida?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Florida, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Florida is August, when tickets cost £132 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of return tickets is £253 and £230 respectively.

What’s the cheapest day of the week to fly from Chicago to Florida?

The average price of all round-trip flights from Chicago to Florida clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Florida on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Thursday is the most expensive day to fly from Chicago to Florida. For your return ticket, we recommend flying on a Wednesday and avoiding Fridays for the best deals.

How far in advance should I book a flight from Chicago to Florida?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Florida, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on a flight from Chicago to Florida, you should book around 2 weeks before departure, which saves you about 26% compared to booking last-minute. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.

Good to know - Cheap tickets from Chicago to Florida

Low seasonSeptember
Cheapest flight£38
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly (22% more expensive on average)
Flight from Chicago to Orlando

Flights from Chicago to Florida: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from Chicago to Florida 
Verified travelerFlew with American AirlinesORD-TPADec 2024
I recommend having movies and songs downloaded on your device.
AyannaFlew with Spirit AirlinesORD-TPAMay 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
LaurenFlew with Spirit AirlinesORD-MCOFeb 2024
If you can get by with a personal item, spirit has the best prices often at the best times to fly chicago to orlando for a weekend

FAQs - booking Florida flights

  • Are pet/service animal relief areas at Tampa International Airport (TPA)?

    The airport has several designated areas for pets and service animals to use for relieving themselves. In the grassy area across the vehicle drives of the departure and arrival area is an outdoor pet relief area. The other pet relief areas are past the security at the gate level on each airside building; the areas have receptacles, drinking sinks, and disposable waste bags.

  • Are there kids-friendly amenities at Chicago O’Hare International Airport (ORD)?

    Yes. ORD provides nursing stations for mothers to pump or feed their kids. The nursing facilities are on Terminal 1, concourse B by Gate B10, Terminal 2, concourse F next to the Crossover between Gates E9 and E5, Terminal 3, concourse L by Gate L6, and Terminal 5, concourse M next to Gate M20. Additionally, ORD has nursing pods on Terminal 1 on concourse B by Gate B7, concourse C by Gates C11 and C23, and on Terminal 2, on concourse E close to Gate E1. On Terminal 2, in the main hall close to Gate F1, a Family Lounge offers a delegated space for kids to play.

  • Is there a rental car center at Tampa International Airport (TPA)?

    TPA has several rental car companies on its premises. To reach TPA’s onsite rental car center you’ll take the SkyConnect Train from the Main Terminal. SIXT, Payless, Alamo, Budget, Avis, National, Enterprise, Hertz, and Dollar are some of the onsite rental car agencies. Moreover, TPA has an off-airport rental car faculty, which is at one's disposal at the end of Blue and Red Luggage Claim via service courtesy vehicle.

  • Are there airline lounges at Chicago O'Hare International Airport (ORD)?

    The United Lounge is on Terminal 1 close to Gates B6, B18, and C16, and Terminal 2 is next to Gate F9. The Admiral’s Club is on Terminal 3 next to Gates G8, L2A, and H6/K6. On Terminal 5, there is the Sky Club next to Gate M13, SAS Lounge next to Gate M19, Swissport Lounge close to Gate M13, and British Airways Lounge close to Gate M17. The United Polaris Lunges is in Terminal 1 near Gate C18. Passengers who don't own membership to the airline clubs in ORD can purchase a day's pass for most of the airline lounges.

  • How does KAYAK find such low prices on flights from Chicago to Florida?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Florida.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Florida?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Florida is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Florida?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Florida with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Florida?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Florida?

    The cheapest time of day to fly to Florida is generally in the evening, when retur flights cost £103 on average. Morning departures are around 45% more expensive than evening flights, on average. The most expensive time of day to fly to Florida is generally in the morning, which is peak travel time and where the average cost of a ticket is £149.

Top tips for finding a cheap flight from Chicago to Florida

  • Chicago International Airport (ORD) is one of the main airports serving the city of Chicago. ORD is a hub for United Airlines and American Airlines both facilitating flights from Chicago to Florida.
  • If you’re looking to unwind and revitalize before your flight to Florida, check out the yoga room in ORD. The yoga room provides complimentary yoga mats as well as a place to stow your belongings. The yoga room is situated in Terminal 3, on the Mezzanine Level, open daily from around 6 am to 10 pm.
  • If you need a place to rest after your flight from Chicago, Orlando International Airport (MCO) has a hotel. The Hyatt Regency Hotel is situated between Terminals A and B.
  • Miami International Airport (MIA) is one of the airports serving the metropolis of Miami and is a hub for American Airlines, which facilitates flights to Florida from Chicago.
  • MIA has a multi-sensory room offering passengers with hidden disabilities a spot to de-stress after their flight. The sensory room is on concourse D adjacent to the TSA security checkpoint 4.

Reviews of the top 3 airlines flying from Chicago to Florida

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Florida. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Florida? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11034 reviews
6.9Entertainment
7.5Boarding
6.4Food
8.0Crew
7.2Comfort
Airline reviews

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

2.0 MediocreAnonymous, Oct 2025ORD - PDX
Read more American Airlines reviews

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

Great! I intend to use Spirit for future flights. No complaints .

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

Very easy boarding! Crew was fantastic and offered us refreshments quickly and efficiently. Quick, nice flight!

My baggage broke and they did not offer me anything. No conversation

It was not good at all, I think the crew could be kinder

Cheap flight but really uncomfortable. Seat cushions flimsy. Jammed in middle seat when flight is not full. They don’t even give you water

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Everything you need to know for your flight from Chicago to Florida

Cabin class types available on flights to Florida

Cabin classes available on flights to Florida. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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