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>

£49 CHEAP FLIGHTS from Florida 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 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

Thu, 20 Nov - Fri, 21 Nov

21:00 - 23:06MCO-ORD

3h 06mdirect

06:48 - 10:30ORD-MCO

2h 42mdirect

£104Spirit Airlines

Find Deal

Thu, 27 Nov - Sun, 30 Nov

21:00 - 23:06MCO-ORD

3h 06mdirect

21:22 - 10:14ORD-MCO

11h 52m1 stop

£110Spirit Airlines

Find Deal

Fri, 23 Jan - Mon, 26 Jan

09:05 - 11:10MCO-ORD

3h 05mdirect

13:45 - 21:25ORD-MCO

6h 40m1 stop

£112Southwest

Find Deal

Tue, 9 Dec - Tue, 9 Dec

10:30 - 12:33MCO-ORD

3h 03mdirect

14:10 - 18:01ORD-MCO

2h 51mdirect

£115United Airlines

Find Deal

Tue, 6 Jan - Thu, 8 Jan

07:30 - 12:15MCO-ORD

5h 45m1 stop

14:15 - 22:00ORD-MCO

6h 45m1 stop

£119Southwest

Find Deal

Thu, 4 Dec - Thu, 11 Dec

09:50 - 11:49TPA-ORD

2h 59mdirect

18:05 - 21:57ORD-TPA

2h 52mdirect

£119United Airlines

Find Deal

Thu, 11 Dec - Mon, 26 Jan

19:06 - 00:01TPA-ORD

5h 55m1 stop

09:52 - 16:50ORD-TPA

5h 58m1 stop

£150Delta

Find Deal

Fri, 16 Jan - Mon, 19 Jan

14:31 - 21:04TPA-ORD

7h 33m1 stop

10:35 - 18:35ORD-TPA

7h 00m1 stop

£150Delta

Find Deal

Wed, 8 Apr - Mon, 13 Apr

11:00 - 17:31MCO-ORD

7h 31m1 stop

11:30 - 23:07ORD-MCO

10h 37m1 stop

£172JetBlue

Find Deal

Sat, 6 Dec - Sat, 13 Dec

11:15 - 10:35JAX-ORD

24h 20m1 stop

11:25 - 10:07ORD-JAX

21h 42m1 stop

£192JetBlue

Find Deal

Cheapest return fare

£104

Typical prices: £113-£244

Spirit Airlines

Thu 20/11Fri 21/11

MCO - ORD • Direct

Cheapest one-way flight

£49

Typical prices: £83-£217

Frontier

Wed 4/3

MCO - ORD • Direct

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

We hope you love your trip to Chicago!

Useful Info

Low season	January
High season	October
Cheapest flight	£49

Best time to beat the crowds (10% less expensive on average)

Most popular time to fly (4% more expensive on average)

Flight from Orlando to Chicago

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 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

Benton Harbor

Crown Point

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 £4,694

Business Class flights to Chicagofrom £1,097

Prem Econ Class flights to Chicagofrom £1,099

Economy class flights to Chicagofrom £34

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

£49 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 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

Everything you should know

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