£67 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 17/9. 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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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

Tue, 28 Jul - Tue, 4 Aug
Delta Logo
11:47 - 16:23
JAX
-
ORD
5h 36m
1 stop
Delta Logo
06:40 - 13:24
ORD
-
JAX
5h 44m
1 stop
£162Delta
Sat, 5 Sep - Mon, 7 Sep
Frontier Logo
13:18 - 19:55
TPA
-
ORD
7h 37m
1 stop
Frontier Logo
00:29 - 20:16
ORD
-
TPA
18h 47m
1 stop
£166Frontier
Sat, 5 Sep - Mon, 7 Sep
Multiple Airlines Logo
13:18 - 19:55
TPA
-
ORD
7h 37m
1 stop
Multiple Airlines Logo
07:55 - 17:12
ORD
-
TPA
8h 17m
1 stop
£170Multiple Airlines
Wed, 22 Jul - Sat, 25 Jul
Frontier Logo
20:59 - 23:10
MCO
-
ORD
3h 11mdirect
Frontier Logo
17:13 - 21:25
ORD
-
MCO
3h 12mdirect
£170Frontier
Tue, 14 Jul - Tue, 28 Jul
Frontier Logo
21:35 - 23:27
TPA
-
ORD
26h 52m
1 stop
Frontier Logo
13:50 - 21:16
ORD
-
TPA
6h 26m
1 stop
£172Frontier
Wed, 15 Jul - Wed, 22 Jul
Frontier Logo
14:25 - 19:53
TPA
-
ORD
6h 28m
1 stop
Frontier Logo
07:15 - 05:54
ORD
-
TPA
21h 39m
1 stop
£173Frontier
Sat, 29 Aug - Tue, 1 Sep
Frontier Logo
12:39 - 20:53
TPA
-
ORD
9h 14m
1 stop
Frontier Logo
06:55 - 18:51
ORD
-
TPA
10h 56m
1 stop
£176Frontier
Wed, 15 Jul - Wed, 22 Jul
United Airlines Logo
07:09 - 09:18
MCO
-
ORD
3h 09mdirect
United Airlines Logo
07:20 - 11:15
ORD
-
MCO
2h 55mdirect
£177United Airlines
Wed, 4 Nov - Wed, 11 Nov
United Airlines Logo
18:40 - 23:15
JAX
-
ORD
5h 35m
1 stop
United Airlines Logo
13:55 - 17:44
ORD
-
JAX
2h 49mdirect
£179United Airlines
Sat, 14 Nov - Wed, 25 Nov
Sun Country Air Logo
11:49 - 10:41
TPA
-
ORD
23h 52m
1 stop
Sun Country Air Logo
10:54 - 18:04
ORD
-
TPA
6h 10m
1 stop
£235Sun Country Air
Useful Info

Good to know - Cheap tickets from Florida to Chicago

Low seasonJanuary
Cheapest flight£67
Best time to beat the crowds (7% less expensive on average)
Most popular time to fly (2% 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.
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
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 £1,091
Business Class flights to Chicagofrom £891
Premium Economy Class flights to Chicagofrom £1,149
Economy class flights to Chicagofrom £34