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.

£82 CHEAP FLIGHTS from Florida to Chicago

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Flight Deals

Cheap Flights from Florida to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Return

One-way

Last minute

Direct

Recent return flight deals from Florida to Chicago

Wed, 21 Oct - Wed, 28 Oct

06:00 - 19:07MCO Orlando-ORD Chicago O'Hare Intl

14h 07m2 stops Baltimore/Washington Dallas/Fort Worth

14:11 - 07:01ORD Chicago O'Hare Intl-MCO Orlando

15h 50m2 stops Houston George Bush Intcntl Atlanta Hartsfield-Jackson

£158Frontier

Fri, 16 Oct - Mon, 19 Oct

17:01 - 23:30TPA Tampa-ORD Chicago O'Hare Intl

7h 29m1 stop Fort Lauderdale

07:00 - 16:11ORD Chicago O'Hare Intl-TPA Tampa

8h 11m1 stop Fort Lauderdale

£158JetBlue

Thu, 14 Jan - Tue, 19 Jan

14:20 - 18:32TPA Tampa-ORD Chicago O'Hare Intl

5h 12m1 stop Atlanta Hartsfield-Jackson

05:30 - 11:16ORD Chicago O'Hare Intl-TPA Tampa

4h 46m1 stop Atlanta Hartsfield-Jackson

£159Delta

Tue, 27 Oct - Tue, 3 Nov

18:54 - 23:57MCO Orlando-ORD Chicago O'Hare Intl

6h 03m1 stop Fort Lauderdale

14:42 - 22:24ORD Chicago O'Hare Intl-MCO Orlando

6h 42m1 stop Fort Lauderdale

£159JetBlue

Sat, 10 Oct - Tue, 20 Oct

18:25 - 23:30MCO Orlando-ORD Chicago O'Hare Intl

6h 05m1 stop Fort Lauderdale

06:10 - 15:41ORD Chicago O'Hare Intl-MCO Orlando

8h 31m1 stop New York John F Kennedy Intl

£159JetBlue

Sat, 10 Oct - Tue, 13 Oct

18:25 - 23:30MCO Orlando-ORD Chicago O'Hare Intl

6h 05m1 stop Fort Lauderdale

14:55 - 22:14ORD Chicago O'Hare Intl-MCO Orlando

6h 19m1 stop Fort Lauderdale

£161JetBlue

Fri, 9 Oct - Sat, 10 Oct

17:01 - 23:30TPA Tampa-ORD Chicago O'Hare Intl

7h 29m1 stop Fort Lauderdale

07:00 - 16:11ORD Chicago O'Hare Intl-TPA Tampa

8h 11m1 stop Fort Lauderdale

£161JetBlue

Tue, 27 Oct - Fri, 30 Oct

18:35 - 20:40TPA Tampa-ORD Chicago O'Hare Intl

3h 05mdirect

17:45 - 21:43ORD Chicago O'Hare Intl-TPA Tampa

2h 58mdirect

£162United Airlines

Fri, 16 Oct - Mon, 19 Oct

12:19 - 14:22TPA Tampa-ORD Chicago O'Hare Intl

3h 03mdirect

13:55 - 17:43ORD Chicago O'Hare Intl-TPA Tampa

2h 48mdirect

£163United Airlines

Tue, 6 Oct - Wed, 7 Oct

09:09 - 13:47MCO Orlando-ORD Chicago O'Hare Intl

5h 38m1 stop Fort Lauderdale

15:00 - 21:35ORD Chicago O'Hare Intl-MCO Orlando

5h 35m1 stop Fort Lauderdale

£164JetBlue

Recent last minute flight deals from Florida to Chicago

Sat, 19 Sep - Fri, 23 Oct

09:00 - 14:27TPA Tampa-ORD Chicago O'Hare Intl

6h 27m1 stop Washington, D.C. Dulles Intl

16:45 - 20:41ORD Chicago O'Hare Intl-TPA Tampa

2h 56mdirect

£246United Airlines

Thu, 24 Sep - Fri, 23 Oct

19:33 - 21:38TPA Tampa-ORD Chicago O'Hare Intl

3h 05mdirect

13:55 - 17:43ORD Chicago O'Hare Intl-TPA Tampa

2h 48mdirect

£271United Airlines

Thu, 24 Sep - Fri, 23 Oct

09:00 - 14:26TPA Tampa-ORD Chicago O'Hare Intl

6h 26m1 stop Washington, D.C. Dulles Intl

13:55 - 17:43ORD Chicago O'Hare Intl-TPA Tampa

2h 48mdirect

£275United Airlines

Tue, 22 Sep - Fri, 16 Oct

07:30 - 09:33TPA Tampa-ORD Chicago O'Hare Intl

3h 03mdirect

16:45 - 20:41ORD Chicago O'Hare Intl-TPA Tampa

2h 56mdirect

£286United Airlines

Wed, 23 Sep - Sat, 26 Sep

08:30 - 13:45TPA Tampa-ORD Chicago O'Hare Intl

6h 15m1 stop Fort Lauderdale

06:00 - 13:08ORD Chicago O'Hare Intl-TPA Tampa

6h 08m1 stop Fort Lauderdale

£289JetBlue

Tue, 22 Sep - Sat, 26 Sep

13:22 - 15:30TPA Tampa-ORD Chicago O'Hare Intl

3h 08mdirect

07:15 - 11:07ORD Chicago O'Hare Intl-TPA Tampa

2h 52mdirect

£294United Airlines

Tue, 22 Sep - Tue, 29 Sep

08:55 - 13:45MCO Orlando-ORD Chicago O'Hare Intl

5h 50m1 stop Fort Lauderdale

15:00 - 21:35ORD Chicago O'Hare Intl-MCO Orlando

5h 35m1 stop Fort Lauderdale

£295JetBlue

Wed, 23 Sep - Sat, 26 Sep

08:30 - 13:45TPA Tampa-ORD Chicago O'Hare Intl

6h 15m1 stop Fort Lauderdale

15:00 - 21:14ORD Chicago O'Hare Intl-TPA Tampa

5h 14m1 stop Fort Lauderdale

£295JetBlue

Tue, 22 Sep - Sat, 26 Sep

13:22 - 15:30TPA Tampa-ORD Chicago O'Hare Intl

3h 08mdirect

07:30 - 15:19ORD Chicago O'Hare Intl-TPA Tampa

6h 49m1 stop Newark

£298United Airlines

Wed, 23 Sep - Wed, 30 Sep

08:30 - 13:45TPA Tampa-ORD Chicago O'Hare Intl

6h 15m1 stop Fort Lauderdale

06:00 - 13:08ORD Chicago O'Hare Intl-TPA Tampa

6h 08m1 stop Fort Lauderdale

£301JetBlue

Useful Info

Low season	January
High season	June
Cheapest flight	£82

Best time to beat the crowds (14% less expensive on average)

Most popular time to fly (22% more expensive on average)

Flight from Tampa to Chicago

Verified travelerFlew with Southwest-Sept 2026

Nothing much. just when it's time to check-in, try to check in at the exact 24 time limit window in order to get one of the earlier seats at the front of the plane

Verified travelerFlew with American Airlines-May 2026

Don’t plan on using overhead bin space if you board after group 4 on any American flights using 737’s. They are frequently full by the time the 4th group boards. And, if your carry on bag has to be checked at the gate, be sure it has nothing breakable inside, as it may not survive that process.

BillFlew with Frontier-Dec 2025

Wear comfortable clothing and make sure you layer. We went from 80o to 30o,

Verified travelerFlew with Air Canada-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-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.