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 round-trip 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.

$77 CHEAP FLIGHTS from Florida to Chicago

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Cheap Flights from Florida to Chicago

Cheap flights from Florida to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Fri, Dec 11 - Mon, Dec 14

11:24 am - 1:59 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 35mnonstop

6:10 am - 10:29 amORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 19mnonstop

$144Frontier

Thu, Nov 12 - Sun, Nov 15

10:22 am - 11:23 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

26h 01m1 stop Baltimore/Washington

7:55 am - 12:02 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 07mnonstop

$144Frontier

Fri, Nov 6 - Mon, Nov 9

9:15 pm - 11:36 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 21mnonstop

7:55 am - 12:02 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 07mnonstop

$144Multiple Airlines

Thu, Feb 25 - Mon, Mar 1

5:55 pm - 11:30 pmFLL Fort Lauderdale-MDW Chicago Midway

6h 35m1 stop Dallas Love Field

6:10 am - 10:10 amMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$147Southwest

Tue, Nov 10 - Wed, Nov 11

5:30 pm - 9:35 pmFLL Fort Lauderdale-MDW Chicago Midway

5h 05m1 stop Lambert-St Louis

1:20 pm - 8:45 pmMDW Chicago Midway-FLL Fort Lauderdale

6h 25m2 stops Atlanta Hartsfield-Jackson Tampa

$147Southwest

Fri, Dec 11 - Mon, Dec 14

10:20 am - 4:04 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

6h 44m1 stop Baltimore/Washington

7:00 am - 11:10 amORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 10mnonstop

$148Multiple Airlines

Mon, Dec 7 - Tue, Dec 8

7:00 am - 9:30 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 30mnonstop

10:55 am - 3:08 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 13mnonstop

$152United Airlines

Tue, Nov 3 - Tue, Nov 10

9:35 pm - 11:57 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 22mnonstop

7:00 am - 11:10 amORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 10mnonstop

$162JetBlue

Thu, Nov 19 - Mon, Nov 23

2:24 pm - 4:52 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 28mnonstop

7:45 pm - 11:59 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 14mnonstop

$169United Airlines

Thu, Nov 19 - Sat, Dec 5

11:05 am - 1:32 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 27mnonstop

2:59 pm - 7:10 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 11mnonstop

$176JetBlue

Sat, Oct 24 - Mon, Oct 26

9:58 pm - 9:21 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

12h 23m1 stop Atlanta Hartsfield-Jackson

8:04 am - 12:12 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 08mnonstop

$149Frontier

Sat, Oct 24 - Mon, Oct 26

9:58 pm - 9:21 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

12h 23m1 stop Atlanta Hartsfield-Jackson

8:04 am - 12:12 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 08mnonstop

$150Frontier

Sat, Oct 24 - Mon, Nov 2

1:52 pm - 6:31 pmTPA Tampa-ORD Chicago O'Hare Intl

5h 39m1 stop Atlanta Hartsfield-Jackson

7:55 am - 9:50 amORD Chicago O'Hare Intl-TPA Tampa

24h 55m1 stop Fort Lauderdale

$283Multiple Airlines

Tue, Oct 20 - Thu, Oct 29

11:00 am - 7:14 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

9h 14m1 stop Boston Logan Intl

7:00 am - 11:10 amORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 10mnonstop

$285JetBlue

Sat, Oct 24 - Sun, Nov 1

1:52 pm - 6:31 pmTPA Tampa-ORD Chicago O'Hare Intl

5h 39m1 stop Atlanta Hartsfield-Jackson

7:55 am - 7:10 amORD Chicago O'Hare Intl-TPA Tampa

22h 15m1 stop Fort Lauderdale

$289Multiple Airlines

Tue, Oct 20 - Mon, Nov 23

7:00 am - 9:30 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 30mnonstop

7:30 pm - 11:41 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 11mnonstop

$295American Airlines

Tue, Oct 20 - Mon, Nov 23

7:10 am - 12:22 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

6h 12m1 stop Charlotte Douglas

7:30 pm - 11:41 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 11mnonstop

$305American Airlines

Tue, Oct 20 - Mon, Nov 23

12:40 pm - 2:45 pmFLL Fort Lauderdale-MDW Chicago Midway

3h 05mnonstop

2:35 pm - 10:35 pmMDW Chicago Midway-FLL Fort Lauderdale

7h 00m1 stop Columbus

$305Southwest

Tue, Oct 20 - Mon, Nov 23

7:00 am - 2:40 pmFLL Fort Lauderdale-MDW Chicago Midway

8h 40m2 stops Orlando Miami

2:35 pm - 10:35 pmMDW Chicago Midway-FLL Fort Lauderdale

7h 00m1 stop Columbus

$320Southwest

Tue, Oct 20 - Fri, Oct 23

11:00 am - 7:14 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

9h 14m1 stop Boston Logan Intl

12:38 pm - 9:59 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

8h 21m1 stop New York John F Kennedy Intl

$322JetBlue

Thu, Nov 19 - Fri, Nov 27

1:05 pm - 3:37 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 32mnonstop

4:00 pm - 8:07 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 07mnonstop

$142Frontier

Thu, Feb 11 - Tue, Feb 16

1:39 pm - 4:14 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 35mnonstop

8:25 am - 12:44 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 19mnonstop

$142Frontier

Fri, Nov 6 - Mon, Nov 9

9:15 pm - 11:36 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 21mnonstop

7:55 am - 12:02 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 07mnonstop

$144Multiple Airlines

Sat, Nov 7 - Mon, Nov 9

11:15 am - 1:42 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 27mnonstop

7:55 am - 12:02 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 07mnonstop

$149Multiple Airlines

Wed, Dec 2 - Sat, Dec 5

6:50 am - 8:55 amFLL Fort Lauderdale-MDW Chicago Midway

3h 05mnonstop

3:30 pm - 7:25 pmMDW Chicago Midway-FLL Fort Lauderdale

2h 55mnonstop

$153Southwest

Tue, Nov 10 - Wed, Nov 11

6:50 am - 8:55 amFLL Fort Lauderdale-MDW Chicago Midway

3h 05mnonstop

6:20 pm - 10:20 pmMDW Chicago Midway-FLL Fort Lauderdale

3h 00mnonstop

$153Southwest

Thu, Nov 19 - Mon, Nov 23

8:22 am - 10:59 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 37mnonstop

7:30 pm - 11:41 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 11mnonstop

$169American Airlines

Thu, Nov 19 - Mon, Nov 23

2:24 pm - 4:52 pmFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 28mnonstop

7:45 pm - 11:59 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 14mnonstop

$169United Airlines

Fri, Nov 20 - Mon, Nov 23

7:00 am - 9:31 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 31mnonstop

7:45 pm - 11:59 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 14mnonstop

$169United Airlines

Thu, Nov 19 - Tue, Dec 1

6:20 am - 9:00 amFLL Fort Lauderdale-ORD Chicago O'Hare Intl

3h 40mnonstop

5:29 pm - 9:36 pmORD Chicago O'Hare Intl-FLL Fort Lauderdale

3h 07mnonstop

$176American Airlines

Low season	January
High season	June
Cheapest flight	$77

Best time to beat the crowds with an average 16% drop in price.

Most popular time to fly with an average 18% increase in price.

Flight from Fort Lauderdale to Chicago Midway Airport

Verified travelerFlew with ITA Airways-Sep 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-Sep 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 round-trip 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.