$393 Cheap Flights from Chicago (MDW) to Florence (FLR)

View $393 flight on Mon, Jan 26, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Florence Airport, Peretola (FLR)

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Chicago to Florence (MDW-FLR)

Prices were available within the past 7 days and start at $393 for one-way flights and $658 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Mar 4 - Thu, Mar 12
MDW
Chicago
FLR
Florence
$658 Roundtrip, found 4 days ago
$658
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Mar 4 from Chicago to Florence, returning Thu, Mar 12, priced at $658 found 4 days ago
Delta
Mon, Jan 26 - Sun, May 17
MDW
Chicago
FLR
Florence
$762 Roundtrip, found 4 hours ago
$762
Roundtrip
found 4 hours ago
Select Delta flight, departing Mon, Jan 26 from Chicago to Florence, returning Sun, May 17, priced at $762 found 4 hours ago
Delta
Wed, Jul 9 - Wed, Jul 16
MDW
Chicago
FLR
Florence
$786 Roundtrip, found 11 hours ago
$786
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Jul 9 from Chicago to Florence, returning Wed, Jul 16, priced at $786 found 11 hours ago
Delta
Tue, Aug 12 - Sun, Aug 17
MDW
Chicago
FLR
Florence
$791 Roundtrip, found 12 hours ago
$791
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Aug 12 from Chicago to Florence, returning Sun, Aug 17, priced at $791 found 12 hours ago
Delta
Tue, Aug 12 - Sun, Aug 17
MDW
Chicago
FLR
Florence
$793 Roundtrip, found 21 hours ago
$793
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Aug 12 from Chicago to Florence, returning Sun, Aug 17, priced at $793 found 21 hours ago
Delta
Tue, Aug 12 - Sun, Aug 17
MDW
Chicago
FLR
Florence
$821 Roundtrip, found 12 hours ago
$821
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Aug 12 from Chicago to Florence, returning Sun, Aug 17, priced at $821 found 12 hours ago
Delta
Wed, Mar 4 - Thu, Mar 12
MDW
Chicago
FLR
Florence
$833 Roundtrip, found 4 days ago
$833
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Mar 4 from Chicago to Florence, returning Thu, Mar 12, priced at $833 found 4 days ago
Delta
Sun, Aug 10 - Thu, Sep 11
MDW
Chicago
FLR
Florence
$842 Roundtrip, found 10 hours ago
$842
Roundtrip
found 10 hours ago
Select Delta flight, departing Sun, Aug 10 from Chicago to Florence, returning Thu, Sep 11, priced at $842 found 10 hours ago
Air France
Fri, Jul 18 - Fri, Jul 25
MDW
Chicago
FLR
Florence
$860 Roundtrip, found 8 hours ago
$860
Roundtrip
found 8 hours ago
Select Air France flight, departing Fri, Jul 18 from Chicago to Florence, returning Fri, Jul 25, priced at $860 found 8 hours ago
KLM
Thu, Jan 1 - Thu, Jan 8
MDW
Chicago
FLR
Florence
$1,138 Roundtrip, found 1 day ago
$1,138
Roundtrip
found 1 day ago
Select KLM flight, departing Thu, Jan 1 from Chicago to Florence, returning Thu, Jan 8, priced at $1,138 found 1 day ago

Alternative airports near Florence

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Peretola FLR. Cheapest and Closest option available. Average driving time to city center is 14 minutes. Flights from $786
FLR
Peretola
CheapestClosest
Average driving time to city center14 min
Flights from $786
Flights from Chicago (MDW) to Florence (FLR)
Origin airport
Midway Intl.
Destination airport
Peretola
Airlines serving
Air France, Delta, KLM
Roundtrip price
$657
Distance
4685 mi

Chicago to Florence Flights

The cheapest times to fly from Chicago to Florence

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Florence are during the month of March. You can find some of the cheapest flights from Chicago to Florence with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Florence

Sunday is one of the best days to book for cheap flights from Chicago to Florence: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Florence

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Florence in 2025. You can also book with separate airlines for your outbound and return journeys, from $393 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Florence flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Florence airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Peretola Airport (FLR) cost?
Discover the latest flight deals from MDW to FLR by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to FLR?
The cheapest flights from MDW to FLR are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MDW to FLR?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to FLR. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Peretola Airport (FLR)?
Direct flights from Midway Intl. Airport (MDW) to Peretola Airport (FLR) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to FLR?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* But this can change based on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Peretola Airport (FLR)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Peretola Airport (FLR) route, travel before 3 PM. Flights after this time have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Peretola Airport (FLR) last-minute?
Holding off until just before your departure to book a flight from MDW to FLR generally means paying more. Although you may find some last-minute offers, there's no guarantee. Keep your travel plans flexible to boost your chances of landing a bargain.
Is it cheaper to book a MDW to FLR flight and hotel package?
Opting for a MDW to FLR flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Choose from our impressive range of hotels and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Peretola Airport (FLR)?
If you booked your MDW to FLR flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

Explore a world of travel with Expedia

*Available to One Key members.