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>

$44 CHEAP FLIGHTS from Florida to Chicago

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

...and more

Travelers love KAYAK

41.299.237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$72

Overall average: $169

Spirit Airlines

Wed 1/28Sat 1/31

MCO - ORD • Non-stop

Cheapest one-way

$44

Typical prices: $106-$244

Spirit Airlines

Fri 1/16

MCO - ORD • Non-stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

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

Wed, Jan 28 - Sat, Jan 31

3:43 pm - 5:52 pm

MCO

ORD

3h 09mnonstop

12:44 pm - 4:31 pm

ORD

MCO

2h 47mnonstop

$72Spirit Airlines

Fri, Feb 20 - Sun, Feb 22

5:47 pm - 8:12 pm

MCO

ORD

3h 25mnonstop

1:17 pm - 5:18 pm

ORD

MCO

3h 01mnonstop

$73Frontier

Fri, Jan 16 - Fri, Jan 23

7:05 am - 9:09 am

MCO

MDW

3h 04mnonstop

1:00 pm - 4:49 pm

MDW

MCO

2h 49mnonstop

$73Frontier

Sat, Jan 31 - Tue, Feb 10

2:18 pm - 4:40 pm

MCO

ORD

3h 22mnonstop

12:44 pm - 4:31 pm

ORD

MCO

2h 47mnonstop

$75Multiple Airlines

Sat, Jan 17 - Tue, Jan 20

12:15 pm - 2:39 pm

MCO

ORD

3h 24mnonstop

5:32 pm - 11:59 pm

ORD

MCO

5h 27m1 stop

$79Multiple Airlines

Tue, Jan 20 - Tue, Jan 27

8:10 am - 12:30 pm

TPA

MDW

5h 20m1 stop

1:25 pm - 5:00 pm

MDW

TPA

2h 35mnonstop

$167Southwest

Thu, Feb 26 - Sat, Feb 28

6:40 am - 8:25 am

TPA

MDW

2h 45mnonstop

6:15 pm - 9:55 pm

MDW

TPA

2h 40mnonstop

$168Southwest

Thu, Jan 15 - Sat, Jan 17

9:00 am - 11:21 am

PBI

ORD

3h 21mnonstop

11:02 am - 3:15 pm

ORD

PBI

3h 13mnonstop

$229United Airlines

Thu, Jan 22 - Mon, Jan 26

4:20 pm - 6:50 pm

PBI

ORD

3h 30mnonstop

5:40 pm - 9:49 pm

ORD

PBI

3h 09mnonstop

$230American Airlines

Fri, May 8 - Sun, May 10

5:03 pm - 11:15 pm

PBI

ORD

7h 12m1 stop

11:10 am - 3:15 pm

ORD

PBI

3h 05mnonstop

$235United Airlines

Useful Info

Low season	February
High season	July
Cheapest flight	$44

Best time to beat the crowds with an average 24% drop in price.

Most popular time to fly with an average 2% increase in price.

Flight from Orlando to Chicago O'Hare Airport

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.

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

Lansing

Valparaiso

Chesterton

Schererville

Munster

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 $315

Business Class flights to Chicagofrom $595

Prem Econ Class flights to Chicagofrom $456

Economy Class flights to Chicagofrom $24

$44 Find Cheap Flights from Florida to Chicago

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

Everything you should know

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