£62 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 23/5. 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, 17 Jun - Wed, 16 Sep
United Airlines Logo
19:42 - 21:53
TPA
-
ORD
3h 11mdirect
United Airlines Logo
10:45 - 14:40
ORD
-
TPA
2h 55mdirect
£124United Airlines
Wed, 27 May - Tue, 2 Jun
Southwest Logo
07:35 - 09:45
MCO
-
ORD
3h 10mdirect
Southwest Logo
19:35 - 23:20
ORD
-
MCO
2h 45mdirect
£124Southwest
Tue, 16 Jun - Tue, 23 Jun
American Airlines Logo
07:52 - 10:00
MCO
-
ORD
3h 08mdirect
American Airlines Logo
18:45 - 22:36
ORD
-
MCO
2h 51mdirect
£125American Airlines
Wed, 27 May - Wed, 3 Jun
United Airlines Logo
19:42 - 21:53
TPA
-
ORD
3h 11mdirect
United Airlines Logo
08:40 - 15:15
ORD
-
TPA
5h 35m
1 stop
£129United Airlines
Wed, 27 May - Wed, 3 Jun
Southwest Logo
08:10 - 13:15
TPA
-
ORD
6h 05m
1 stop
Southwest Logo
14:00 - 17:50
ORD
-
TPA
2h 50mdirect
£132Southwest
Wed, 27 May - Wed, 3 Jun
Southwest Logo
14:00 - 16:05
TPA
-
ORD
3h 05mdirect
Southwest Logo
14:00 - 17:50
ORD
-
TPA
2h 50mdirect
£135Southwest
Wed, 27 May - Sat, 30 May
United Airlines Logo
09:40 - 11:48
MCO
-
ORD
3h 08mdirect
United Airlines Logo
14:00 - 17:57
ORD
-
MCO
2h 57mdirect
£135United Airlines
Tue, 16 Jun - Tue, 23 Jun
United Airlines Logo
19:27 - 21:38
TPA
-
ORD
3h 11mdirect
United Airlines Logo
17:56 - 21:49
ORD
-
TPA
2h 53mdirect
£138United Airlines
Tue, 16 Jun - Wed, 16 Sep
Delta Logo
14:00 - 20:31
TPA
-
ORD
7h 31m
1 stop
Delta Logo
13:15 - 18:56
ORD
-
TPA
4h 41m
1 stop
£145Delta
Wed, 3 Jun - Tue, 9 Jun
Delta Logo
06:15 - 10:16
MCO
-
ORD
5h 01m
1 stop
Delta Logo
11:23 - 18:44
ORD
-
MCO
6h 21m
1 stop
£145Delta
Useful Info

Good to know - Cheap tickets from Florida to Chicago

Low seasonJanuary
Cheapest flight£62
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (6% 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
New Buffalo
Valparaiso
Schererville
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 £1,076
Business Class flights to Chicagofrom £878
Premium Economy Class flights to Chicagofrom £1,132
Economy class flights to Chicagofrom £33