£52 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 21/4. 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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Flight Deals

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

Wed, 29 Apr - Wed, 6 May
Multiple Airlines Logo
10:58 - 13:00
MCO
-
ORD
3h 02mdirect
Multiple Airlines Logo
15:55 - 19:51
ORD
-
MCO
2h 56mdirect
£81Multiple Airlines
Wed, 29 Apr - Wed, 6 May
Frontier Logo
06:45 - 15:17
MCO
-
ORD
9h 32m
1 stop
Frontier Logo
15:55 - 19:51
ORD
-
MCO
2h 56mdirect
£92Frontier
Fri, 15 May - Mon, 18 May
Spirit Airlines Logo
15:10 - 17:10
TPA
-
ORD
3h 00mdirect
Spirit Airlines Logo
10:26 - 14:05
ORD
-
TPA
2h 39mdirect
£96Spirit Airlines
Fri, 1 May - Fri, 8 May
Multiple Airlines Logo
21:51 - 23:58
TPA
-
ORD
3h 07mdirect
Multiple Airlines Logo
10:26 - 14:05
ORD
-
TPA
2h 39mdirect
£97Multiple Airlines
Fri, 17 Apr - Fri, 24 Apr
Spirit Airlines Logo
16:18 - 18:20
TPA
-
ORD
3h 02mdirect
Spirit Airlines Logo
20:52 - 00:29
ORD
-
TPA
2h 37mdirect
£104Spirit Airlines
Fri, 1 May - Fri, 8 May
Frontier Logo
15:30 - 22:39
MCO
-
ORD
8h 09m
1 stop
Frontier Logo
17:30 - 21:32
ORD
-
MCO
3h 02mdirect
£109Frontier
Wed, 15 Apr - Wed, 22 Apr
Southwest Logo
06:30 - 12:50
JAX
-
ORD
7h 20m
1 stop
Southwest Logo
11:55 - 22:15
ORD
-
JAX
9h 20m
2 stops
£194Southwest
Tue, 21 Apr - Thu, 7 May
United Airlines Logo
11:32 - 13:23
JAX
-
ORD
2h 51mdirect
United Airlines Logo
14:00 - 17:45
ORD
-
JAX
2h 45mdirect
£195United Airlines
Sat, 25 Apr - Tue, 28 Apr
United Airlines Logo
08:00 - 09:50
JAX
-
ORD
2h 50mdirect
United Airlines Logo
13:00 - 20:02
ORD
-
JAX
6h 02m
1 stop
£196United Airlines
Wed, 15 Apr - Wed, 22 Apr
Southwest Logo
11:50 - 21:55
JAX
-
ORD
11h 05m
2 stops
Southwest Logo
11:55 - 22:15
ORD
-
JAX
9h 20m
2 stops
£197Southwest
Useful Info

Good to know - Cheap tickets from Florida to Chicago

Low seasonJanuary
Cheapest flight£52
Best time to beat the crowds (2% less expensive on average)
Most popular time to fly (1% more expensive 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.
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
Hammond
Lansing
Valparaiso
Schererville
New Buffalo
Crown Point
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 £4,640
Business Class flights to Chicagofrom £895
Premium Economy Class flights to Chicago
Economy class flights to Chicagofrom £34