£116 Find Cheap Flights from Florida to Chicago

This is the cheapest return flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 30/10. 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

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Cheap Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Florida to Chicago

Thu, 30 Oct - Mon, 3 Nov
United Airlines Logo
08:00 - 09:44JAX-ORD
2h 44mdirect
United Airlines Logo
07:05 - 10:33ORD-JAX
2h 28mdirect
£116United Airlines
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Wed, 20 Aug - Wed, 27 Aug
United Airlines Logo
12:35 - 14:36TPA-ORD
3h 01mdirect
United Airlines Logo
11:12 - 15:02ORD-TPA
2h 50mdirect
£116United Airlines
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Fri, 25 Jul - Fri, 1 Aug
Frontier Logo
21:18 - 23:31MCO-ORD
3h 13mdirect
Frontier Logo
16:26 - 20:28ORD-MCO
3h 02mdirect
£117Frontier
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Thu, 4 Sep - Mon, 8 Sep
Southwest Logo
07:10 - 13:05TPA-ORD
6h 55m1 stop
Southwest Logo
12:40 - 23:00ORD-TPA
9h 20m1 stop
£130Southwest
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Mon, 18 Aug - Wed, 20 Aug
Southwest Logo
05:35 - 15:20JAX-ORD
10h 45m2 stops
Southwest Logo
13:50 - 20:40ORD-JAX
5h 50m1 stop
£134Southwest
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Thu, 21 Aug - Mon, 25 Aug
Delta Logo
19:51 - 23:56JAX-ORD
5h 05m1 stop
Delta Logo
09:10 - 16:47ORD-JAX
6h 37m1 stop
£145Delta
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Sat, 12 Jul - Wed, 16 Jul
Delta Logo
05:20 - 10:10TPA-ORD
5h 50m1 stop
Delta Logo
07:00 - 15:23ORD-TPA
7h 23m1 stop
£145Delta
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Fri, 25 Jul - Fri, 1 Aug
Spirit Airlines Logo
21:59 - 07:04MCO-ORD
10h 05m1 stop
Spirit Airlines Logo
16:37 - 23:00ORD-MCO
5h 23m1 stop
£152Spirit Airlines
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Sat, 28 Jun - Tue, 1 Jul
Spirit Airlines Logo
19:07 - 21:19TPA-ORD
3h 12mdirect
Spirit Airlines Logo
05:05 - 17:49ORD-TPA
11h 44m2 stops
£183Spirit Airlines
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Thu, 25 Sep - Sun, 28 Sep
Frontier Logo
15:31 - 00:10JAX-ORD
9h 39m2 stops
Frontier Logo
05:10 - 15:58ORD-JAX
9h 48m1 stop
£288Frontier
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Good to know - Cheap tickets from Florida to Chicago

Low seasonJanuary
High seasonAugust
Cheapest flight£48
Best time to beat the crowds (10% less expensive on average)
Most popular time to fly and prices are also 11% lower on average.
Flight from Orlando 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.
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
New Buffalo
Lansing
Crown Point
Chesterton
Valparaiso

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 £557
Business Class flights to Chicagofrom £727
Prem Econ Class flights to Chicagofrom £1,066
Economy class flights to Chicagofrom £72

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