£52 Find Cheap Flights from Chicago to Florida – Compare and Save

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Cheap Flights from Chicago to Florida

Cheapest return flight prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Fort Lauderdale
2h 59mNonstop
from £88per person
Miami
3h 08mNonstop
from £130per person
Orlando
2h 48mNonstop
from £149per person
Tampa
2h 50mNonstop
from £156per person
Jacksonville
2h 34mNonstop
from £178per person
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 return flight from Chicago to Florida?

Flight prices are below average for this route right now.

Flights to Florida from Chicago usually cost between £160 and £320 in October.
The lowest price found in the past 5 days was £130 on United Airlines (10 Oct–13 Oct).

What is the cheapest Chicago to Florida flight route?

The cheapest ticket to Florida from Chicago found in the last 5 days was to Orlando, at £98 return. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Fort Myers (RSW), and the cheapest return airline ticket found on this route in the last 5 days was £269.

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

The cheapest time of day to fly to Florida is generally in the morning, when retur flights cost £437 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 £437.

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

No, with an average price for the route of £292, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Chicago to Florida is January, when tickets cost £169 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of return tickets is £264 and £259 respectively.

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

To get a below-average price on a flight from Chicago to Florida, you should book around 3 weeks before departure, which saves you about 26% compared to booking last-minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know - Cheap tickets from Chicago to Florida

Low season

September
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly (10% more expensive on average)

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

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

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.

More options for your flight from Chicago to Florida

Complete your trip to Florida with a hotel stay or car hire