£66 Find Cheap Flights from Florida to Chicago – Compare and Save

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 22/9. 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

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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

Tue, 6 Oct - Thu, 8 Oct
Frontier Logo
20:51 - 22:59
MCO
-
ORD
3h 08mdirect
Frontier Logo
07:00 - 17:56
ORD
-
MCO
9h 56m
1 stop
£146Frontier
Wed, 16 Dec - Sat, 9 Jan
United Airlines Logo
18:40 - 23:15
JAX
-
ORD
5h 35m
1 stop
United Airlines Logo
07:30 - 11:11
ORD
-
JAX
2h 41mdirect
£146United Airlines
Sat, 22 Aug - Tue, 25 Aug
United Airlines Logo
19:10 - 23:40
JAX
-
ORD
5h 30m
1 stop
United Airlines Logo
12:56 - 20:54
ORD
-
JAX
6h 58m
1 stop
£150United Airlines
Mon, 21 Sep - Fri, 25 Sep
Frontier Logo
20:51 - 22:59
MCO
-
ORD
3h 08mdirect
Frontier Logo
11:15 - 15:08
ORD
-
MCO
2h 53mdirect
£152Frontier
Sat, 22 Aug - Mon, 24 Aug
United Airlines Logo
19:10 - 23:40
JAX
-
ORD
5h 30m
1 stop
United Airlines Logo
10:29 - 14:04
ORD
-
JAX
2h 35mdirect
£154United Airlines
Thu, 10 Sep - Fri, 11 Sep
United Airlines Logo
16:45 - 18:34
JAX
-
ORD
2h 49mdirect
United Airlines Logo
12:55 - 20:54
ORD
-
JAX
6h 59m
1 stop
£155United Airlines
Wed, 2 Sep - Sun, 6 Sep
Delta Logo
17:34 - 20:55
JAX
-
ORD
4h 21m
1 stop
Delta Logo
06:40 - 11:44
ORD
-
JAX
4h 04m
1 stop
£158Delta
Thu, 27 Aug - Thu, 3 Sep
Frontier Logo
21:02 - 07:53
TPA
-
ORD
11h 51m
2 stops
Frontier Logo
13:59 - 00:35
ORD
-
TPA
9h 36m
1 stop
£158Frontier
Thu, 10 Sep - Tue, 15 Sep
United Airlines Logo
13:22 - 15:30
TPA
-
ORD
3h 08mdirect
United Airlines Logo
14:16 - 21:36
ORD
-
TPA
6h 20m
1 stop
£158United Airlines
Sat, 29 Aug - Mon, 31 Aug
United Airlines Logo
16:23 - 18:31
TPA
-
ORD
3h 08mdirect
United Airlines Logo
08:45 - 15:28
ORD
-
TPA
5h 43m
1 stop
£160United Airlines
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Good to know - Cheap tickets from Florida to Chicago

Low season

January
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly and prices are also 15% lower on average.

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 American Airlines
RSW
-
ORD
May 2026
Don’t plan on using overhead bin space if you board after group 4 on any American flights using 737’s. They are frequently full by the time the 4th group boards. And, if your carry on bag has to be checked at the gate, be sure it has nothing breakable inside, as it may not survive that process.
BillFlew with Frontier
MCO
-
ORD
Dec 2025
Wear comfortable clothing and make sure you layer. We went from 80o to 30o,
Verified travelerFlew with Air Canada
JAX
-
ORD
Apr 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 Southwest
TPA
-
MDW
Mar 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
Saint Joseph
Hammond
Lansing
Valparaiso
New Buffalo
Schererville
Benton Harbor
Chesterton

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 £1,086
Business Class flights to Chicagofrom £886
Premium Economy Class flights to Chicagofrom £1,143
Economy class flights to Chicagofrom £132