£64 Find Cheap Flights from Florida to Chicago – Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 34% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Florida to Chicago

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

Recent return flight deals from Florida to Chicago

Wed, 2 Dec - Sat, 5 Dec
JetBlue Logo
21:10 - 23:33FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 23mdirect
JetBlue Logo
14:59 - 19:10ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 11mdirect
£113JetBlue
Tue, 22 Dec - Tue, 22 Dec
United Airlines Logo
08:35 - 11:09FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 34mdirect
United Airlines Logo
20:03 - 00:29ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 26mdirect
£114United Airlines
Wed, 10 Feb - Sun, 14 Feb
United Airlines Logo
14:13 - 16:44FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 31mdirect
United Airlines Logo
17:55 - 22:11ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 16mdirect
£119United Airlines
Wed, 23 Dec - Wed, 30 Dec
United Airlines Logo
16:10 - 18:45FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 35mdirect
United Airlines Logo
20:03 - 00:29ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 26mdirect
£124United Airlines
Wed, 23 Dec - Tue, 29 Dec
United Airlines Logo
16:10 - 18:45FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 35mdirect
United Airlines Logo
20:03 - 00:29ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 26mdirect
£126United Airlines
Wed, 10 Feb - Sun, 14 Feb
United Airlines Logo
12:28 - 15:01FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 33mdirect
United Airlines Logo
12:51 - 20:34ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
6h 43m1 stop Washington, D.C. Dulles Intl
£127United Airlines
Fri, 20 Nov - Tue, 1 Dec
United Airlines Logo
07:00 - 09:31FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 31mdirect
United Airlines Logo
19:45 - 23:59ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 14mdirect
£127United Airlines
Wed, 2 Dec - Fri, 4 Dec
JetBlue Logo
08:00 - 16:42FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
9h 42m1 stop Boston Logan Intl
JetBlue Logo
07:00 - 11:10ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 10mdirect
£130JetBlue
Tue, 1 Dec - Tue, 8 Dec
JetBlue Logo
21:10 - 23:33FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 23mdirect
JetBlue Logo
07:00 - 11:10ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 10mdirect
£134JetBlue
Fri, 18 Dec - Tue, 22 Dec
United Airlines Logo
08:35 - 11:09FLL  Fort Lauderdale-ORD Chicago O'Hare Intl
3h 34mdirect
United Airlines Logo
20:03 - 00:29ORD  Chicago O'Hare Intl-FLL Fort Lauderdale
3h 26mdirect
£137United Airlines
Useful Info

Good to know - Cheap tickets from Florida to Chicago

Low season

January

Cheapest flight

£64
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (17% more expensive on average)
Flight from Fort Lauderdale to Chicago

Flights from Florida to Chicago: the best tips from KAYAK users

Insights shared by verified travellers who flew the route from Florida to Chicago 
Verified travelerFlew with ITA Airways-Sept 2026
If you have a connecting flight in Chicago check which terminal it boards from and transport there asap since Chicago is a huge airport. There was a very helpful very small desk tucked away downstairs that was able to assist with getting a number of passengers on an airport shuttle. I arrived at the terminal as the connecting flight was boarding. One clue, if you don't see your flight on the screen it might be at a different terminal.
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.

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?

Book flights to Chicago if you plan to visit one of these locations
New Buffalo
Saint Joseph
Hammond
Valparaiso
Schererville
Lansing
Benton Harbor
Chesterton
Merrillville

More options for your flight to Chicago