Cheap flights from Florence to Chicago

Compare Florence to Chicago flight deals

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Flight deals from Florence to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Florence Airport to Chicago? If you want to travel next month, round-trip fares start from $791. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$609 per passenger.Departing Fri, Oct 9, returning Sun, Oct 11.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Florence on Fri, Oct 9, arriving in Chicago O'Hare International.Inbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Sun, Oct 11, arriving in Florence.Price includes taxes and charges.From $609, select.

Chicago.$610 per passenger.Departing Thu, Sep 17, returning Sun, Sep 27.Round-trip flight with TAP Air Portugal.Outbound indirect flight with TAP Air Portugal, departing from Florence on Thu, Sep 17, arriving in Chicago O'Hare International.Inbound indirect flight with TAP Air Portugal, departing from Chicago O'Hare International on Sun, Sep 27, arriving in Florence.Price includes taxes and charges.From $610, select.

Chicago.$690 per passenger.Departing Wed, Sep 30, returning Tue, Oct 6.Round-trip flight with Iberia and British Airways.Outbound indirect flight with Iberia, departing from Florence on Wed, Sep 30, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Tue, Oct 6, arriving in Florence.Price includes taxes and charges.From $690, select.

Chicago.$690 per passenger.Departing Sat, Nov 21, returning Sat, Dec 5.Round-trip flight with Iberia and British Airways.Outbound indirect flight with Iberia, departing from Florence on Sat, Nov 21, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Sat, Dec 5, arriving in Florence.Price includes taxes and charges.From $690, select.

Chicago.$699 per passenger.Departing Mon, Aug 31, returning Fri, Oct 30.Round-trip flight with British Airways.Outbound indirect flight with British Airways, departing from Florence on Mon, Aug 31, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Fri, Oct 30, arriving in Florence.Price includes taxes and charges.From $699, select.

Chicago.$699 per passenger.Departing Sun, May 9, returning Tue, May 18.Round-trip flight with British Airways.Outbound indirect flight with British Airways, departing from Florence on Sun, May 9, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Tue, May 18, arriving in Florence.Price includes taxes and charges.From $699, select.

Chicago.$706 per passenger.Departing Wed, Aug 19, returning Thu, Aug 27.Round-trip flight with Scandinavian Airlines and Icelandair.Outbound indirect flight with Scandinavian Airlines, departing from Florence on Wed, Aug 19, arriving in Chicago O'Hare International.Inbound indirect flight with Icelandair, departing from Chicago O'Hare International on Thu, Aug 27, arriving in Florence.Price includes taxes and charges.From $706, select.

Chicago.$746 per passenger.Departing Tue, Jun 9, returning Tue, Jun 23.Round-trip flight with ITA Airways.Outbound indirect flight with ITA Airways, departing from Florence on Tue, Jun 9, arriving in Chicago O'Hare International.Inbound indirect flight with ITA Airways, departing from Chicago O'Hare International on Tue, Jun 23, arriving in Florence.Price includes taxes and charges.From $746, select.

Chicago.$752 per passenger.Departing Sat, Nov 7, returning Tue, Nov 17.Round-trip flight with British Airways.Outbound indirect flight with British Airways, departing from Florence on Sat, Nov 7, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Tue, Nov 17, arriving in Florence.Price includes taxes and charges.From $752, select.

Chicago.$757 per passenger.Departing Sat, Dec 5, returning Mon, Dec 7.Round-trip flight with British Airways.Outbound indirect flight with British Airways, departing from Florence on Sat, Dec 5, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Mon, Dec 7, arriving in Florence.Price includes taxes and charges.From $757, select.

Chicago.$774 per passenger.Departing Mon, Mar 22, returning Sun, Mar 28.Round-trip flight with SWISS.Outbound indirect flight with SWISS, departing from Florence on Mon, Mar 22, arriving in Chicago O'Hare International.Inbound indirect flight with SWISS, departing from Chicago O'Hare International on Sun, Mar 28, arriving in Florence.Price includes taxes and charges.From $774, select.

Chicago.$777 per passenger.Departing Wed, Mar 24, returning Thu, Apr 1.Round-trip flight with Lufthansa.Outbound indirect flight with Lufthansa, departing from Florence on Wed, Mar 24, arriving in Chicago O'Hare International.Inbound indirect flight with Lufthansa, departing from Chicago O'Hare International on Thu, Apr 1, arriving in Florence.Price includes taxes and charges.From $777, select.

Chicago.$788 per passenger.Departing Wed, Aug 5, returning Thu, Sep 10.Round-trip flight with Scandinavian Airlines.Outbound indirect flight with Scandinavian Airlines, departing from Florence on Wed, Aug 5, arriving in Chicago O'Hare International.Inbound indirect flight with Scandinavian Airlines, departing from Chicago O'Hare International on Thu, Sep 10, arriving in Florence.Price includes taxes and charges.From $788, select.

Chicago.$791 per passenger.Departing Tue, Jul 21, returning Tue, Jul 28.Round-trip flight with Iberia and British Airways.Outbound indirect flight with Iberia, departing from Florence on Tue, Jul 21, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Tue, Jul 28, arriving in Florence.Price includes taxes and charges.From $791, select.

Chicago.$795 per passenger.Departing Mon, Dec 21, returning Tue, Jan 5.Round-trip flight with British Airways.Outbound indirect flight with British Airways, departing from Florence on Mon, Dec 21, arriving in Chicago O'Hare International.Inbound indirect flight with British Airways, departing from Chicago O'Hare International on Tue, Jan 5, arriving in Florence.Price includes taxes and charges.From $795, select.

Chicago.$882 per passenger.Departing Sat, Jun 27, returning Fri, Jul 3.Round-trip flight with Vueling Airlines and jetBlue.Outbound indirect flight with Vueling Airlines, departing from Florence on Sat, Jun 27, arriving in Chicago Midway.Inbound indirect flight with jetBlue, departing from Chicago O'Hare International on Fri, Jul 3, arriving in Florence.Price includes taxes and charges.From $882, select.

Find the cheapest month to fly from Florence to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Florence to Chicago flights are currently cheapest in October.

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Alternative Florence to Chicago routes

Looking for the cheapest, fastest or easiest route from Florence to Chicago? You could fly into the following airports instead.

Florence to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$609
Cheapest month to fly	October

Finding cheap flights from Florence to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are round-trip flights from Florence to Chicago?

The best price we found for a round-trip flight from Florence to Chicago is $609. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Florence to Chicago?

Currently, there are no airlines that fly direct from Florence to Chicago. But we found flights with one or more stops from $609.

How many flights are there a week from Florence to Chicago?

There are no flights flying from Florence to Chicago, as of June 2026.

When is the cheapest time to fly from Florence to Chicago?

The cheapest month to fly from Florence to Chicago is usually October.

What's the cheapest airport to fly to in Chicago?

If you're flying from Florence Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from $609.

Which upcoming date is cheapest to fly from Florence Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Florence Airport to Chicago on Friday, October 9, 2026.

Can I get a direct flight from Florence Airport to Chicago?

No airlines currently offer direct flights between Florence Airport and Chicago. Most routes have one or more stops.

How can I get the best flight deal from Florence Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly with from Florence Airport to Chicago?

Currently, TAP Air Portugal offers the cheapest flight tickets to Chicago.

Flying from Florence Peretola Airport (FLR) to Chicago: what you need to know

Florence Peretola Airport is located in Florence. Following the UTC-6 timezone, Chicago is seven hours behind Florence.
Give yourself enough time to make your FLR to Chicago flight. As a rule of thumb, arrive at least two hours before international departures and an hour ahead for domestic flights.
You'll likely experience longer lines during popular months like September. Arriving up to four hours ahead of international flights and two hours for domestic departures will help ensure a smooth travel experience.
Think about adding a stopover to potentially save on your plane ticket from FLR to Chicago. All you need to do is uncheck 'Direct flights only' during your search. Take a detour (and maybe pocket some savings) by stopping at one of these airports:
- Frankfurt Airport (FRA)
- Paris Charles de Gaulle Airport (CDG)
- Munich Franz Joseph Strauss Airport (MUC)
The journey from central Florence to FLR takes around 25 minutes by public transport. If you drive, ride-share or grab a cab, you'll cover the 6 kilometers in 20 minutes or so, depending on traffic conditions.
Booked an early flight from Florence Peretola Airport to Chicago? Avoid the stress of rushing to the terminal (and sneak in some extra snooze time) by choosing one of these hotels close to FLR:
74% of flights that leave from Florence Peretola Airport make it to their destination on schedule.

How to find the cheapest flights from Florence Peretola Airport (FLR) to Chicago

$390 is currently the lowest price for a one-way Florence Peretola Airport to Chicago flight. A return plane ticket starts at $609. These fares may change based on demand and availability.
Booking early is often the key to locking in a cheap flight from FLR to Chicago. Fares tend to rise as demand increases, so the closer you get to departure, the more you'll likely pay.
If you're flexible with your travel dates, take advantage of the 'Whole month' search tool. It'll give you the cheapest price across every month when looking for your Florence Peretola Airport to Chicago ticket.
Locking in a cheap flight from FLR to Chicago is easy with Price Alerts. Simply set up one of these automatic notifications and we'll let you know as soon as a better deal is available.
Tailor your trip with filters. Pick your departure and arrival times, airlines and total journey duration. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Florence Peretola Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

The distance from Chicago O'Hare International Airport (ORD) to central Chicago is roughly 27 kilometers. It'll take you around 30 minutes to reach the center driving.
If you're traveling on public transport, expect a journey time of around 45 minutes.
Look into staying at a hotel close to ORD if you're coming in on a late flight from Florence Peretola Airport to Chicago. Choose one of these accommodation options and skip the long transfer:
For the lowest price, reserve your ride from Chicago O'Hare International Airport around four weeks ahead of your flight from FLR to Chicago.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) is roughly 16 kilometers from the center of Chicago. Following your flight from Florence Peretola Airport to Chicago, it'll take you around 25 minutes to reach the heart of the city in a cab or ride-share.
If you choose to travel on public transport, the journey will take you 30 minutes or so.
After stepping off your FLR to Chicago flight, kick back at a hotel close to MDW. These are some comfortable accommodation options that'll help you switch to relaxation mode:
Avoid potential price surges. Securing your ride four weeks before your arrival at MDW can land you a better rate.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Chicago Rockford International Airport (RFD) is around 145 kilometers from central Chicago. It'll take you about 1 hour 40 minutes to reach the city center by cab or ride-share after your flight from Florence Peretola Airport to Chicago.
If you're traveling on public transport, the journey takes about 2 hours.
Choose a hotel close to RFD and go from landing to lounging in your room in a flash. Whether you're coming in on a late FLR to Chicago flight or just want a stress-free arrival, these stays are all about convenience:
Rental companies sometimes offer discounts on early bookings, so reserve your vehicle from RFD well ahead of your flight from Florence Peretola Airport to Chicago. A little prep work can make a big difference in cost.
Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

July is the most popular month for flights from Florence Peretola Airport to Chicago. To escape the crowds, plan your trip to Chicago in January.
Book a Florence Peretola Airport to Chicago plane ticket with a departure in July if you want to explore the city during its warmest month. You can expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).
If you'd rather travel in cooler conditions, search for a cheap ticket from FLR to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

When it comes to looking for somewhere to rest your head, you'll find the best places to stay in Chicago right here. Explore these hotels as soon as you've locked in your flight from Florence Peretola Airport to Chicago:
Every great adventure has to include a little sightseeing. Art Institute of Chicago, Millennium Park and Willis Tower are attractions you won't want to skip in Chicago.

Explore more of the United States

You've visited Chicago, now it's time to explore other corners of the United States. Journey around 451 kilometers southeast to Columbus to tick off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theater, you've got a jam-packed schedule ahead.
If you're looking to explore another corner of the United States, consider Indianapolis, roughly 257 kilometers southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among the biggest draws.