$38 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 9/19. 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

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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, Jul 23 - Tue, Jul 29
Spirit Airlines Logo
6:20 pm - 8:28 pmMCO-ORD
3h 08mnonstop
Spirit Airlines Logo
4:36 pm - 8:23 pmORD-MCO
2h 47mnonstop
$85Spirit Airlines
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Fri, Sep 5 - Mon, Sep 8
Frontier Logo
4:53 pm - 11:20 pmTPA-MDW
7h 27m1 stop
Frontier Logo
6:21 am - 9:57 amMDW-TPA
2h 36mnonstop
$87Frontier
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Wed, Jul 23 - Wed, Jul 30
Logo
6:20 pm - 8:28 pmMCO-ORD
3h 08mnonstop
Logo
11:28 am - 3:24 pmORD-MCO
2h 56mnonstop
$87
Find Deal
Tue, Jul 29 - Wed, Jul 30
Logo
9:03 pm - 11:11 pmMCO-ORD
3h 08mnonstop
Logo
11:28 am - 3:24 pmORD-MCO
2h 56mnonstop
$91
Find Deal
Fri, Sep 5 - Sun, Sep 7
United Airlines Logo
12:27 pm - 2:55 pmMIA-ORD
3h 28mnonstop
United Airlines Logo
10:54 am - 3:10 pmORD-MIA
3h 16mnonstop
$137United Airlines
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Thu, Aug 21 - Sun, Aug 24
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
Southwest Logo
8:05 am - 12:10 pmMDW-MIA
3h 05mnonstop
$137Southwest
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Fri, Oct 3 - Wed, Oct 8
Southwest Logo
11:50 am - 1:55 pmMIA-MDW
3h 05mnonstop
Southwest Logo
5:25 am - 12:15 pmMDW-MIA
5h 50m1 stop
$147Southwest
Find Deal
Fri, Jul 25 - Mon, Jul 28
American Airlines Logo
6:41 pm - 8:58 pmPBI-ORD
3h 17mnonstop
American Airlines Logo
8:22 am - 12:19 pmORD-PBI
2h 57mnonstop
$179American Airlines
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Thu, Jul 24 - Mon, Jul 28
American Airlines Logo
6:41 pm - 8:58 pmPBI-ORD
3h 17mnonstop
American Airlines Logo
8:22 am - 12:19 pmORD-PBI
2h 57mnonstop
$180American Airlines
Find Deal
Thu, Sep 18 - Sat, Sep 20
United Airlines Logo
8:00 am - 9:44 amJAX-ORD
2h 44mnonstop
United Airlines Logo
6:26 pm - 9:58 pmORD-JAX
2h 32mnonstop
$181United Airlines
Find Deal
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$38
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Miami 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 Air CanadaJAX-ORDApr 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 SouthwestTPA-MDWMar 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.

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 $435
Business Class flights to Chicagofrom $669
Prem Econ Class flights to Chicagofrom $463
Economy Class flights to Chicagofrom $24

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