$62 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 8/30. 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 round-trip 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 round-trip flight deals from Florida to Chicago

Sun, Aug 23 - Wed, Aug 26
Frontier Logo
10:18 am - 12:50 pm
FLL
-
ORD
3h 32mnonstop
Frontier Logo
8:05 am - 12:28 pm
ORD
-
FLL
3h 23mnonstop
$138Frontier
Sun, Aug 23 - Wed, Aug 26
Frontier Logo
10:18 am - 12:50 pm
FLL
-
ORD
3h 32mnonstop
Frontier Logo
8:05 am - 12:28 pm
ORD
-
FLL
3h 23mnonstop
$140Frontier
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
11:00 am - 1:39 pm
FLL
-
ORD
3h 39mnonstop
Multiple Airlines Logo
8:05 am - 12:28 pm
ORD
-
FLL
3h 23mnonstop
$147Multiple Airlines
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
7:10 am - 9:10 am
FLL
-
MDW
3h 00mnonstop
Southwest Logo
6:20 pm - 10:15 pm
MDW
-
FLL
2h 55mnonstop
$171Southwest
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
7:10 am - 9:10 am
FLL
-
MDW
3h 00mnonstop
Southwest Logo
10:10 am - 3:20 pm
MDW
-
FLL
4h 10m
1 stop
$177Southwest
Thu, Aug 13 - Thu, Aug 20
American Airlines Logo
7:26 am - 10:00 am
MIA
-
ORD
3h 34mnonstop
American Airlines Logo
6:00 am - 10:07 am
ORD
-
MIA
3h 07mnonstop
$182American Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
10:10 pm - 12:33 am
MIA
-
ORD
3h 23mnonstop
American Airlines Logo
2:29 pm - 6:46 pm
ORD
-
MIA
3h 17mnonstop
$183American Airlines
Sat, Sep 5 - Mon, Sep 7
United Airlines Logo
3:57 pm - 6:30 pm
MIA
-
ORD
3h 33mnonstop
United Airlines Logo
7:30 am - 11:54 am
ORD
-
MIA
3h 24mnonstop
$187United Airlines
Sat, Aug 29 - Sat, Sep 5
United Airlines Logo
9:00 am - 2:27 pm
TPA
-
ORD
6h 27m
1 stop
United Airlines Logo
4:30 pm - 8:26 pm
ORD
-
TPA
2h 56mnonstop
$215United Airlines
Mon, Aug 17 - Fri, Aug 21
Multiple Airlines Logo
10:29 am - 2:59 pm
MCO
-
MDW
5h 30m
1 stop
Multiple Airlines Logo
11:50 am - 8:00 pm
MDW
-
MCO
7h 10m
1 stop
$215Multiple Airlines
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Good to know

Low season

January

Cheapest flight

$62
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Jacksonville to Chicago O'Hare Airport

Flights from Florida to Chicago: the best tips from KAYAK users

Insights shared by verified travelers 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 round-trip 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Munster
Chesterton
Porter
Monticello
Saint John
Griffith

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 $577
Business Class flights to Chicagofrom $598
Premium Economy Class flights to Chicagofrom $273
Economy Class flights to Chicagofrom $76