$75 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 10/27. 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

Wed, Oct 7 - Sun, Oct 11
Frontier Logo
12:53 pm - 3:20 pm
FLL
-
ORD
3h 27mnonstop
Frontier Logo
7:45 am - 11:55 am
ORD
-
FLL
3h 10mnonstop
$135Frontier
Sat, Sep 5 - Sun, Sep 6
Frontier Logo
10:18 am - 12:50 pm
FLL
-
ORD
3h 32mnonstop
Frontier Logo
8:05 am - 12:28 pm
ORD
-
FLL
3h 23mnonstop
$136Frontier
Wed, Sep 9 - Wed, Sep 16
Multiple Airlines Logo
12:53 pm - 3:20 pm
FLL
-
ORD
3h 27mnonstop
Multiple Airlines Logo
9:38 am - 6:06 pm
ORD
-
FLL
7h 28m
1 stop
$141Multiple Airlines
Thu, Oct 8 - Mon, Oct 12
Multiple Airlines Logo
12:57 pm - 3:26 pm
FLL
-
ORD
3h 29mnonstop
Multiple Airlines Logo
2:35 pm - 6:49 pm
ORD
-
FLL
3h 14mnonstop
$142Multiple Airlines
Tue, Dec 8 - Tue, Dec 15
American Airlines Logo
8:35 am - 11:05 am
FLL
-
ORD
3h 30mnonstop
American Airlines Logo
7:13 pm - 11:23 pm
ORD
-
FLL
3h 10mnonstop
$149American Airlines
Wed, Dec 2 - Wed, Dec 9
American Airlines Logo
12:59 pm - 3:29 pm
FLL
-
ORD
3h 30mnonstop
American Airlines Logo
4:56 pm - 9:10 pm
ORD
-
FLL
3h 14mnonstop
$149American Airlines
Tue, Oct 13 - Tue, Oct 13
Southwest Logo
6:50 am - 9:00 am
FLL
-
MDW
3h 10mnonstop
Southwest Logo
5:55 pm - 9:50 pm
MDW
-
FLL
2h 55mnonstop
$149Southwest
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
4:55 pm - 7:00 pm
FLL
-
MDW
3h 05mnonstop
Southwest Logo
8:35 am - 12:40 pm
MDW
-
FLL
3h 05mnonstop
$149Southwest
Mon, Oct 26 - Wed, Oct 28
United Airlines Logo
9:05 am - 11:33 am
FLL
-
ORD
3h 28mnonstop
United Airlines Logo
7:00 am - 11:08 am
ORD
-
FLL
3h 08mnonstop
$160United Airlines
Wed, Oct 14 - Thu, Oct 15
United Airlines Logo
12:32 pm - 3:00 pm
FLL
-
ORD
3h 28mnonstop
United Airlines Logo
7:00 am - 11:14 am
ORD
-
FLL
3h 14mnonstop
$160United Airlines
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Good to know

Low season

January

Cheapest flight

$75
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Fort Lauderdale to Chicago Midway 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
Munster
Schererville
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 $288
Business Class flights to Chicagofrom $214
Premium Economy Class flights to Chicagofrom $181
Economy Class flights to Chicagofrom $76