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>

£37 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 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

Tue, 14 Oct - Tue, 21 Oct

15:53 - 17:53MCO-ORD

3h 00mdirect

06:00 - 09:44ORD-MCO

2h 44mdirect

£74Spirit Airlines

Find Deal

Wed, 29 Oct - Wed, 5 Nov

14:26 - 16:23MCO-ORD

2h 57mdirect

06:05 - 09:48ORD-MCO

2h 43mdirect

£74Spirit Airlines

Find Deal

Wed, 29 Oct - Wed, 5 Nov

20:59 - 00:43MCO-ORD

28h 44m1 stop

06:05 - 09:48ORD-MCO

2h 43mdirect

£94Multiple Airlines

Find Deal

Wed, 29 Oct - Wed, 5 Nov

15:05 - 17:12MCO-ORD

27h 07m1 stop

07:20 - 05:44ORD-MCO

21h 24m1 stop

£106Frontier

Find Deal

Sat, 8 Nov - Tue, 11 Nov

09:30 - 11:29TPA-ORD

2h 59mdirect

07:30 - 11:20ORD-TPA

2h 50mdirect

£108United Airlines

Find Deal

Fri, 7 Nov - Tue, 11 Nov

16:20 - 18:20TPA-ORD

3h 00mdirect

07:30 - 11:20ORD-TPA

2h 50mdirect

£109United Airlines

Find Deal

Sat, 8 Nov - Tue, 11 Nov

09:30 - 11:29TPA-ORD

2h 59mdirect

09:15 - 18:32ORD-TPA

8h 17m1 stop

£113United Airlines

Find Deal

Sat, 8 Nov - Tue, 11 Nov

12:45 - 14:45TPA-ORD

3h 00mdirect

13:45 - 21:30ORD-TPA

6h 45m1 stop

£116Southwest

Find Deal

Tue, 14 Oct - Tue, 21 Oct

18:18 - 20:23MCO-ORD

3h 05mdirect

14:15 - 18:06ORD-MCO

2h 51mdirect

£116United Airlines

Find Deal

Wed, 15 Oct - Wed, 22 Oct

06:30 - 15:20TPA-ORD

9h 50m2 stops

16:20 - 23:25ORD-TPA

6h 05m1 stop

£119Southwest

Find Deal

Cheapest return fare

£74

Overall average: £143

Spirit Airlines

Tue 14/10Tue 21/10

MCO - ORD • Direct

Cheapest one-way flight

£37

Typical prices: £65-143

Spirit Airlines

Sat 7/2

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	£37

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

Most popular time to fly (7% 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

Benton Harbor

Valparaiso

Schererville

New Buffalo

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 £4,551

Business Class flights to Chicagofrom £727

Prem Econ Class flights to Chicagofrom £1,066

Economy class flights to Chicagofrom £33

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

£37 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