Cheap flights from Chicago to Tuscany from $174
This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Tuscany departing on 11/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Tuscany
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Tuscany?
The month of November is, on average, the cheapest month to fly to Tuscany from Chicago, with most prices found around $756. If you’re not able to fly to Tuscany in November, then October is your next best option. Flight prices from Chicago to Tuscany during October average around $814.
What is the cheapest day to depart on your flight to Tuscany?
On average, the least expensive day to fly to Tuscany from Chicago is on a Sunday. momondo users have found tickets for Sunday departures for as low as $984. However, this price may fluctuate depending on the airline, the season, and holidays. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $1,399. These prices are subject to change though, so be sure to set up a Price Alert for flights to Tuscany.
What is the cheapest time of day to depart on your flight to Tuscany?
Our data shows that the cheapest Chicago to Tuscany flights are usually those with departure times in the morning. Our users have found flights to Tuscany in the morning for as low as $900. At noon is when there is more demand to fly to Tuscany, so prices are often more expensive at around $1,583 per ticket.
How far in advance should I book a flight to Tuscany?
You are more likely to see cheaper flights to Tuscany from Chicago when booking 8 weeks ahead of your departure date. In general, you can expect to find flights to Tuscany for around $1,058 when searching 8 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Tuscany from Chicago for as low as $909 on momondo.
What is the cheapest airline that flies from Chicago to Tuscany?
Icelandair, TAP AIR PORTUGAL, and Turkish Airlines are the most popular carriers operating from Chicago to Tuscany
What airlines fly to Tuscany?
ITA Airways, British Airways and Delta are the top three most popular airlines that fly to Tuscany from Chicago according to our data. ITA Airways is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Tuscany. Keep in mind that there are 10 different airlines that fly to Tuscany on a routine basis, so you have a few additional options to choose from.
Cheap Chicago to Tuscany flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Tuscany
When did momondo last update prices for flights from Chicago to Tuscany?
Prices for flights from Chicago to Tuscany were last updated today.
How many operators does momondo search for flights from Chicago to Tuscany?
As of June 2025, there are 18 operators available to choose from for flights from Chicago to Tuscany.
How old do you have to be to fly from Chicago to Tuscany?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Tuscany.
What documentation or ID do you need to fly to Tuscany?
The required travel and health documents for your Tuscany trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Tuscany. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
Best airlines flying from Chicago to Tuscany
Compare and see reviews for airlines that fly from Chicago to Tuscany with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $470 | Free Cancellation | Rating 7.3 1,387 reviews | |||
| PriceFrom $627 | Free Cancellation | Rating 6.6 7,008 reviews | |||
| PriceFrom $651 | Free Cancellation | Rating 7.8 1,358 reviews | |||
| PriceFrom $666 | Free Cancellation | Rating 7.5 1,463 reviews | |||
| PriceFrom $684 | Free Cancellation | Rating 6.7 7,139 reviews | |||
| PriceFrom $710 | Free Cancellation | Rating 7.5 1,623 reviews | |||
| PriceFrom $711 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $729 | Free Cancellation | Rating 6.7 990 reviews | |||
| PriceFrom $737 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $792 | Free Cancellation | Rating 7.0 2,776 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Tuscany?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Tuscany from Chicago.
Can I find flights from Chicago to Tuscany with flexible booking policies on momondo?
momondo does allow users to show only those flights to Tuscany from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Tuscany?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Tuscany.
I’m not ready to book a flight from Chicago to Tuscany right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Tuscany from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.