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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$52 CHEAP FLIGHTS from Florida to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

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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.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Florida to Chicago

Fri, Sep 19 - Sun, Sep 21

5:24 pm - 7:44 pmMCO-ORD

3h 20mnonstop

8:49 pm - 12:35 amORD-MCO

2h 46mnonstop

$95Frontier

Find Deal

Sat, Aug 30 - Sat, Sep 6

2:07 pm - 4:10 pmMCO-ORD

3h 03mnonstop

5:17 pm - 9:06 pmORD-MCO

2h 49mnonstop

$96Spirit Airlines

Find Deal

Tue, Sep 16 - Sun, Sep 21

6:31 am - 10:52 amMCO-ORD

5h 21m1 stop

8:49 pm - 12:35 amORD-MCO

2h 46mnonstop

$98

Find Deal

Sat, Sep 20 - Wed, Sep 24

1:02 pm - 3:17 pmMCO-ORD

3h 15mnonstop

5:17 pm - 9:06 pmORD-MCO

2h 49mnonstop

$102

Find Deal

Fri, Sep 26 - Mon, Sep 29

12:35 pm - 2:45 pmMIA-MDW

3h 10mnonstop

2:10 pm - 6:10 pmMDW-MIA

3h 00mnonstop

$137Southwest

Find Deal

Fri, Sep 26 - Mon, Sep 29

6:15 pm - 12:05 amMIA-MDW

6h 50m1 stop

2:10 pm - 6:10 pmMDW-MIA

3h 00mnonstop

$147Southwest

Find Deal

Sat, Sep 13 - Mon, Sep 15

7:59 pm - 10:26 pmMIA-ORD

3h 27mnonstop

6:09 am - 10:14 amORD-MIA

3h 05mnonstop

$158American Airlines

Find Deal

Sat, Sep 27 - Tue, Sep 30

10:48 am - 6:23 pmPBI-ORD

8h 35m1 stop

9:51 am - 6:18 pmORD-PBI

7h 27m1 stop

$217JetBlue

Find Deal

Sat, Nov 1 - Mon, Nov 3

11:20 am - 8:52 pmPBI-ORD

10h 32m1 stop

6:44 am - 4:38 pmORD-PBI

8h 54m1 stop

$220JetBlue

Find Deal

Fri, Oct 31 - Tue, Nov 4

10:43 am - 5:13 pmPNS-ORD

6h 30m1 stop

10:30 am - 1:00 pmORD-PNS

2h 30mnonstop

$224American Airlines

Find Deal

Useful Info

Low season	January
High season	October
Cheapest flight	$52

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly and prices are also 3% lower on average.

Flight from Orlando to Chicago Midway Airport

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.

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.

Merrillville

Saint Joseph

Hammond

Portage

Valparaiso

Lansing

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Florida

First Class flights to Chicagofrom $165

Business Class flights to Chicagofrom $482

Prem Econ Class flights to Chicagofrom $205

Economy Class flights to Chicagofrom $24

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

$52 Find Cheap Flights from Florida to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Cheap Flights from Florida to Chicago

Recent round-trip flight deals from Florida to Chicago

Recent one-way flight deals from Florida to Chicago

Recent last minute flight deals from Florida to Chicago

Recent direct flight deals from Florida to Chicago

Good to know

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

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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Florida

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight