$85 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 11/17. 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.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Florida.
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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$175
Miami
Miaminonstop$230
Fort Lauderdale
Fort Lauderdalenonstop$126
Tampa
Tampa1 stop$205
Fort Myers
Fort Myers2 stops$282
West Palm Beach
West Palm Beachnonstop$289
Jacksonville
Jacksonville1 stop$220
Sarasota
Sarasota1 stop$237
Pensacola
Pensacola1 stop$237
Key West
Key West1 stop$262
Valparaiso
Valparaisononstop$96
Panama City
Panama Citynonstop$305
Punta Gorda
Punta Gordanonstop$123
Tallahassee
Tallahassee1 stop$371
Gainesville
Gainesville1 stop$399
Orlando
Orlandononstop$175
Miami
Miaminonstop$230
Fort Lauderdale
Fort Lauderdalenonstop$126
Tampa
Tampa1 stop$205
Fort Myers
Fort Myers2 stops$282
West Palm Beach
West Palm Beachnonstop$289
Jacksonville
Jacksonville1 stop$220
Sarasota
Sarasota1 stop$237
Pensacola
Pensacola1 stop$237
Key West
Key West1 stop$262
Valparaiso
Valparaisononstop$96
Panama City
Panama Citynonstop$305
Punta Gorda
Punta Gordanonstop$123
Tallahassee
Tallahassee1 stop$371
Gainesville
Gainesville1 stop$399

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

mar, lug 28 - mar, ago 4
Multiple Airlines Logo
2:35 pm - 6:49 pm
ORD
-
FLL
3h 14mnonstop
Multiple Airlines Logo
9:43 am - 12:15 pm
FLL
-
ORD
3h 32mnonstop
$126Multiple Airlines
mar, lug 28 - mar, ago 4
Multiple Airlines Logo
2:35 pm - 6:49 pm
ORD
-
FLL
3h 14mnonstop
Multiple Airlines Logo
9:43 am - 12:15 pm
FLL
-
ORD
3h 32mnonstop
$127Multiple Airlines
mer, ago 19 - sab, ago 29
Frontier Logo
8:05 am - 12:28 pm
ORD
-
FLL
3h 23mnonstop
Frontier Logo
10:18 am - 12:50 pm
FLL
-
ORD
3h 32mnonstop
$128Frontier
mar, lug 14 - sab, lug 18
Frontier Logo
8:05 am - 12:22 pm
ORD
-
FLL
3h 17mnonstop
Frontier Logo
9:43 am - 12:15 pm
FLL
-
ORD
3h 32mnonstop
$129Frontier
sab, ago 15 - sab, ago 22
Southwest Logo
6:15 am - 10:05 am
MDW
-
FLL
2h 50mnonstop
Southwest Logo
6:40 am - 8:40 am
FLL
-
MDW
3h 00mnonstop
$171Southwest
mer, lug 29 - mer, ago 5
Southwest Logo
11:15 am - 5:15 pm
MDW
-
FLL
5h 00m
1 stop
Southwest Logo
7:20 am - 9:20 am
FLL
-
MDW
3h 00mnonstop
$177Southwest
sab, ago 8 - mer, ago 12
American Airlines Logo
5:59 pm - 9:48 pm
ORD
-
TPA
2h 49mnonstop
American Airlines Logo
6:23 am - 8:30 am
TPA
-
ORD
3h 07mnonstop
$209American Airlines
gio, ago 13 - lun, ago 17
United Airlines Logo
7:15 am - 11:11 am
ORD
-
TPA
2h 56mnonstop
United Airlines Logo
5:23 pm - 11:26 pm
TPA
-
ORD
7h 03m
1 stop
$215United Airlines
sab, ago 1 - sab, ago 8
United Airlines Logo
6:05 pm - 10:27 pm
ORD
-
MIA
3h 22mnonstop
United Airlines Logo
6:30 am - 12:29 pm
MIA
-
ORD
6h 59m
1 stop
$230United Airlines
mer, lug 22 - mer, lug 29
American Airlines Logo
4:05 pm - 8:26 pm
ORD
-
MIA
3h 21mnonstop
American Airlines Logo
9:55 am - 2:20 pm
MIA
-
ORD
5h 25m
1 stop
$236American Airlines
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Florida departing in August.

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 5 days was to Fort Lauderdale, at $76 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 5 days was $147.

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

The average price for all round-trip flights from Chicago to Florida depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida is generally at night, when round-trip flights cost $251 on average. Morning departures are around 18% 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 $322.

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 $335, 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 January, when tickets cost $220 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $343 and $339 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 Sunday, 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 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$85
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago O'Hare Airport to Fort Lauderdale

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

Insights shared by verified travelers who flew the route from Chicago to Florida 
SteveFlew with Spirit Airlines
ORD
-
MCO
Mar 2026
Bring a seat cushion if you're flying Spirit.
Verified travelerFlew with American Airlines
ORD
-
TPA
Dec 2024
I recommend having movies and songs downloaded on your device.
AyannaFlew with Spirit Airlines
ORD
-
TPA
May 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
LaurenFlew with Spirit Airlines
ORD
-
MCO
Feb 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.

Top tips for finding cheap flights 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 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.
7.9
SouthwestOverall score based on 4249 reviews
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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.

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 experience. WiFi worked on this leg of My trip

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Always wish for more healthy, gluten free options. We have to bring our own.

Our seats were all the way in back of the plane,

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

The Airline was not prepared for weather delays. We were held up due to an incoming flight being delayed and so we did not have a flight crew. This caused an extra delay for departure by 2 hours.

From the moment I walked into the airport in Chicago to the moment I was walking off the plane in Florida I had an unforgettable experience! I was traveling with my 3 month old by myself and everyone just made sure I was taken care of. I couldn’t thank them enough!

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

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.

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

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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.