£60 Find Cheap Flights from Florida to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 25/6. 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.
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Cheap Flight Deals from Florida to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Florida to Chicago 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.

Recent return flight deals from Florida to Chicago

KAYAK's recommended return flight deals from the most popular airlines that fly from Florida to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
22:17 - 00:36MCO-ORD
3h 19mdirect
Frontier Logo
17:08 - 21:09ORD-MCO
3h 01mdirect
£72Frontier
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Wed, 4 Jun - Sat, 7 Jun
Logo
21:42 - 08:50MCO-ORD
12h 08m1 stop
Logo
17:08 - 21:09ORD-MCO
3h 01mdirect
£94
Find Deal
Wed, 4 Jun - Sat, 7 Jun
United Airlines Logo
07:30 - 09:34TPA-ORD
3h 04mdirect
United Airlines Logo
07:30 - 11:21ORD-TPA
2h 51mdirect
£119United Airlines
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Thu, 17 Jul - Sun, 20 Jul
Spirit Airlines Logo
18:09 - 09:24MCO-ORD
16h 15m1 stop
Spirit Airlines Logo
05:51 - 14:40ORD-MCO
7h 49m1 stop
£123Spirit Airlines
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Wed, 4 Jun - Sat, 7 Jun
Delta Logo
14:09 - 18:37TPA-ORD
5h 28m1 stop
Delta Logo
05:30 - 11:28ORD-TPA
4h 58m1 stop
£147Delta
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Fri, 30 May - Sun, 1 Jun
Delta Logo
20:00 - 23:58TPA-ORD
4h 58m1 stop
Delta Logo
05:35 - 11:41ORD-TPA
5h 06m1 stop
£148Delta
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Thu, 26 Jun - Fri, 4 Jul
Southwest Logo
11:00 - 13:05MCO-ORD
3h 05mdirect
Southwest Logo
06:00 - 09:40ORD-MCO
2h 40mdirect
£148Southwest
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Wed, 21 May - Sat, 24 May
Spirit Airlines Logo
06:07 - 23:04MCO-ORD
17h 57m2 stops
Spirit Airlines Logo
12:41 - 20:37ORD-MCO
6h 56m1 stop
£154Spirit Airlines
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Wed, 4 Jun - Sat, 7 Jun
Southwest Logo
06:15 - 11:50TPA-ORD
6h 35m1 stop
Southwest Logo
13:50 - 20:50ORD-TPA
6h 00m1 stop
£163Southwest
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Sat, 30 Aug - Tue, 2 Sep
United Airlines Logo
16:08 - 18:25TPA-ORD
3h 17mdirect
United Airlines Logo
07:30 - 11:21ORD-TPA
2h 51mdirect
£193United Airlines
Find Deal
Thu, 22 May - Mon, 26 May
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Good to know - Cheap tickets from Florida to Chicago

Low season

January

High season

May

Cheapest flight

£60
Best time to beat the crowds (10% less expensive on average)
Most popular time to fly and prices are also 6% lower on average.
Flight from Tampa to Chicago

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

Insights shared by verified travellers who flew the route from Florida to Chicago 
Learn how KAYAK collects reviews and tips from users.
Verified travelerFlew with Air CanadaJAX-ORDApr 2025
Chicago is a huge airport, wear comfortable shoes if you're looking to make a connection. It might be a 15 minute speed walk. Jacksonville is a little more compact and easier to navigate. Lots of food and beverage options in each.
JaneFlew with Spirit AirlinesTPA-ORDApr 2025
Tampa Airport is actually quite nice. I can't comment on Chicago since that trip didn't actually happen. As per airlines, I think Allegiant actually does a pretty good job for being a low-cost carrier. JetBlue is nice too.
Verified travelerFlew with FrontierMCO-MDWJan 2025
Tips? Don't fly Frontier and you'll enjoy yourself immensely!!
RachelFlew with SouthwestTPA-MDWJan 2025
Tampa Intl was a surprisingly easy airport to navigate!
Verified travelerFlew with Spirit AirlinesFLL-ORDOct 2024
Please leave on time. Arrive on time and don’t make people wait almost an hour to off board.
Verified travelerFlew with Spirit AirlinesRSW-ORDApr 2024
Fly with Southwest, they are the best, good customer service, flexible schedule, no extra charge for luggage, several flights a day, comparable price. If you don't want to be stranded, DO NOT fly on Spirit!
CindyFlew with SouthwestTPA-MDWMar 2024
Don’t check a bag. Chicago takes forever to get your baggage.

FAQs for booking flights from Florida to Chicago

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

    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 Florida to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from 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 Florida to Chicago?

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

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

    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 to Chicago from Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Chesterton
New Buffalo
Lansing
Crown Point
Valparaiso
Munster
Saint Joseph

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Florida

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom £565
Business Class flights to Chicagofrom £737
Prem Econ Class flights to Chicagofrom £1,080
Economy class flights to Chicagofrom £73

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