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 return 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>

£45 CHEAP FLIGHTS from Florida to Chicago

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

...and more

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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 return fare

£55

Typical prices: £88-£221

Spirit Airlines

Fri 16/1Sun 18/1

MCO - ORD • Direct

Cheapest one-way flight

£45

Typical prices: £58-£130

Spirit Airlines

Fri 27/2

MCO - ORD • Direct

Start a new search

KAYAK searches hundreds 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 return 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 return flight deals from Florida to Chicago

Fri, 16 Jan - Sun, 18 Jan

17:28 - 19:41

MCO

ORD

3h 13mdirect

12:44 - 16:31

ORD

MCO

2h 47mdirect

£55Spirit Airlines

Fri, 6 Feb - Sun, 8 Feb

17:28 - 19:41

MCO

ORD

3h 13mdirect

12:44 - 16:31

ORD

MCO

2h 47mdirect

£74Spirit Airlines

Wed, 14 Jan - Fri, 16 Jan

10:05 - 21:03

TPA

ORD

11h 58m1 stop

20:43 - 07:40

ORD

TPA

9h 57m1 stop

£81Spirit Airlines

Thu, 8 Jan - Tue, 13 Jan

14:57 - 16:58

TPA

ORD

3h 01mdirect

05:15 - 17:33

ORD

TPA

11h 18m1 stop

£86Spirit Airlines

Wed, 21 Jan - Wed, 21 Jan

09:36 - 11:38

TPA

ORD

3h 02mdirect

15:45 - 19:38

ORD

TPA

2h 53mdirect

£113United Airlines

Wed, 7 Jan - Sun, 18 Jan

16:30 - 18:34

TPA

ORD

3h 04mdirect

15:45 - 19:38

ORD

TPA

2h 53mdirect

£115United Airlines

Wed, 21 Jan - Wed, 21 Jan

08:25 - 12:15

TPA

ORD

4h 50m1 stop

13:45 - 21:05

ORD

TPA

6h 20m1 stop

£128Southwest

Thu, 15 Jan - Sun, 18 Jan

19:40 - 21:50

MCO

ORD

3h 10mdirect

15:45 - 19:30

ORD

MCO

2h 45mdirect

£132Southwest

Thu, 5 Mar - Sun, 8 Mar

06:00 - 11:48

TPA

ORD

6h 48m1 stop

12:41 - 20:57

ORD

TPA

7h 16m1 stop

£134JetBlue

Thu, 5 Feb - Sun, 8 Feb

12:00 - 17:43

JAX

ORD

6h 43m1 stop

08:45 - 19:15

ORD

JAX

9h 30m1 stop

£176JetBlue

Useful Info

Low season	January
High season	December
Cheapest flight	£45

Best time to beat the crowds (9% less expensive on average)

Most popular time to fly (16% more expensive on average)

Flight from Orlando to Chicago

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 return 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.

Hammond

Valparaiso

Schererville

New Buffalo

Crown Point

Benton Harbor

Chesterton

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct flights

Flights to other cities

Origins

Return flight deals

Cabin class types available on flights to Florida

First Class flights to Chicagofrom £4,625

Business Class flights to Chicagofrom £1,080

Prem Econ Class flights to Chicago

Economy class flights to Chicagofrom £34

£45 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 return 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 - Cheap tickets from Florida to Chicago

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 return 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.

Travelling 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 hire

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Find deals for your return flight