$49 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 12/16. 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

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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Florida

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Orlando
Orlandononstop$92
Miami
Miaminonstop$104
Fort Lauderdale
Fort Lauderdalenonstop$97
Tampa
Tampanonstop$99
Fort Myers
Fort Myersnonstop$119
West Palm Beach
West Palm Beachnonstop$229
Jacksonville
Jacksonville1 stop$204
Sarasota
Sarasota1 stop$204
Pensacola
Pensacolanonstop$203
Key West
Key West1 stop$215
Panama City
Panama City1 stop$141
Valparaiso
Valparaisononstop$139
Punta Gorda
Punta Gordanonstop$121
Tallahassee
Tallahassee1 stop$317
Gainesville
Gainesville1 stop$329
Orlando
Orlandononstop$92
Miami
Miaminonstop$104
Fort Lauderdale
Fort Lauderdalenonstop$97
Tampa
Tampanonstop$99
Fort Myers
Fort Myersnonstop$119
West Palm Beach
West Palm Beachnonstop$229
Jacksonville
Jacksonville1 stop$204
Sarasota
Sarasota1 stop$204
Pensacola
Pensacolanonstop$203
Key West
Key West1 stop$215
Panama City
Panama City1 stop$141
Valparaiso
Valparaisononstop$139
Punta Gorda
Punta Gordanonstop$121
Tallahassee
Tallahassee1 stop$317
Gainesville
Gainesville1 stop$329

Book Cheap Chicago to Florida Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip 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 round-trip flight deals from Chicago to Florida

Sat, Oct 25 - Wed, Oct 29
Frontier Logo
7:43 pm - 11:37 pmORD-MCO
2h 54mnonstop
Frontier Logo
8:59 pm - 12:43 amMCO-ORD
28h 44m1 stop
$92Frontier
Find Deal
Sat, Oct 4 - Thu, Oct 9
Frontier Logo
11:21 am - 3:04 pmMDW-MCO
2h 43mnonstop
Frontier Logo
9:00 am - 4:42 pmMCO-MDW
8h 42m1 stop
$92Frontier
Find Deal
Tue, Oct 14 - Sat, Oct 18
Spirit Airlines Logo
6:58 pm - 10:50 pmORD-MCO
2h 52mnonstop
Spirit Airlines Logo
7:30 pm - 9:33 pmMCO-ORD
3h 03mnonstop
$93Spirit Airlines
Find Deal
Wed, Oct 15 - Mon, Oct 20
Spirit Airlines Logo
7:43 pm - 11:49 pmORD-FLL
3h 06mnonstop
Spirit Airlines Logo
4:18 pm - 6:38 pmFLL-ORD
3h 20mnonstop
$97Spirit Airlines
Find Deal
Wed, Dec 10 - Tue, Dec 16
United Airlines Logo
9:20 am - 1:26 pmORD-RSW
3h 06mnonstop
United Airlines Logo
9:20 am - 11:32 amRSW-ORD
3h 12mnonstop
$157United Airlines
Find Deal
Mon, Nov 10 - Fri, Nov 14
Southwest Logo
9:30 am - 1:35 pmMDW-MIA
3h 05mnonstop
Southwest Logo
6:20 am - 8:35 amMIA-MDW
3h 15mnonstop
$157Southwest
Find Deal
Tue, Dec 2 - Sat, Dec 6
Southwest Logo
7:30 am - 3:35 pmMDW-TPA
7h 05m1 stop
Southwest Logo
7:05 am - 8:50 amTPA-MDW
2h 45mnonstop
$157Southwest
Find Deal
Tue, Nov 4 - Thu, Nov 13
United Airlines Logo
7:25 am - 11:26 amORD-RSW
3h 01mnonstop
United Airlines Logo
4:38 pm - 6:50 pmRSW-ORD
3h 12mnonstop
$159United Airlines
Find Deal
Wed, Oct 29 - Fri, Nov 7
American Airlines Logo
11:00 am - 3:00 pmORD-RSW
3h 00mnonstop
American Airlines Logo
3:48 pm - 6:14 pmRSW-ORD
3h 26mnonstop
$161American Airlines
Find Deal
Sat, Nov 15 - Mon, Nov 17
American Airlines Logo
12:11 pm - 4:05 pmORD-RSW
2h 54mnonstop
American Airlines Logo
6:00 am - 8:19 amRSW-ORD
3h 19mnonstop
$178American 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.

How much is a round-trip flight from Chicago to Florida?

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 Tampa, at $44 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Orlando Airport (MCO), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $85.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $309, prices are generally cheapest when you fly direct.

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 $174 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $337 and $314 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 you are looking for a flight deal from Chicago to Florida, look for departures on Tuesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Florida, Friday is the cheapest day to fly and Monday is the most expensive.

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 the flight from Chicago to Florida, you should book around 2 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$49
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago O'Hare Airport to Orlando Airport

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

Insights shared by verified travelers 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 travelers 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 round-trip 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 round-trip flights cost $240 on average. Morning departures are around 20% more expensive than evening flights, on average. The most expensive time of day to fly to Florida is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $304.

Top tips for finding cheap flights to Florida

  • Looking for a cheap flight? 25% of our users found tickets from Chicago to the following destinations at these prices or less: Miami $137 one-way - $112 round-trip
  • 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 5 airlines serving 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.
8.0
SouthwestOverall score based on 4242 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

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.

You were more on time than United. I'm so over united delays.

I never made my flight because of their poor service, as I said in my other review: I never made this flight. When I got to the airport I had a message to say that the flight was delayed and would be getting into Fort Lauderdale at 10 pm. My connecting flight was due to leave around 10:10 pm so there is no way I would have made the connection. I went back to the Spirit desk and tried to explain this to a desk agent who didn't understand. Eventually her supervisor came over and explained it. The desk agent was unhelpful and only offered options that would have required getting a hotel overnight. She offered no hotel or meal vouchers and when I said that it seemed my only option was to go to another airline she told me I needed to make a decision because they were closing the desk and would not be back till 3 pm. I went to Delta and had to pay extra but they could help get me back to Orlando. I now have to file a claim against Spirit and I am just glad I paid for insurance. Very unhappy and very poor service.

I never made this flight. When I got to the airport I had a message to say that the flight was delayed and would be getting into Fort Lauderdale at 10 pm. My connecting flight was due to leave around 10:10 pm so there is no way I would have made the connection. I went back to the Spirit desk and tried to explain this to a desk agent who didn't understand. Eventually her supervisor came over and explained it. The desk agent was unhelpful and only offered options that would have required getting a hotel overnight. She offered no hotel or meal vouchers and when I said that it seemed my only option was to go to another airline she told me I needed to make a decision because they were closing the desk and would not be back till 3 pm. I went to Delta and had to pay extra but they could help get me back to Orlando. I now have to file a claim against Spirit and I am just glad I paid for insurance. Very unhappy and very poor service.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Wow truly top notch airline Efficient nice snacks courteous staff Fast boarding !

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

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

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.