$303 Find Cheap Flights from Chicago Midway Airport to Tuscany

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Tuscany departing on 1/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Tuscany, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Tuscany, as well as popular online travel agencies
In the last 7 days travelers have searched 46,646,933 times on KAYAK, and here is why:

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Best Tuscany Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Florence
Florence2 stops$639

Good to know

Cheapest flight

$303
Flight from Chicago Midway Airport to Rome

FAQs - booking Tuscany flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Tuscany?

    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 Chicago Midway Airport to Tuscany.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Tuscany?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Tuscany from Chicago Midway Airport 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 Chicago Midway Airport to Tuscany?

    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 Tuscany with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Tuscany?

    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 Tuscany from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Tuscany

  • Morning departure is around 2% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 airlines serving from Midway to Tuscany

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Tuscany. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Tuscany? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
SouthwestOverall score based on 5005 reviews
7.2Food
7.7Entertainment
8.2Boarding
8.1Comfort
8.7Crew
Airline reviews

This was a nicer flight - not fully booked and so we were able to spread out.

10.0 ExcellentJohn, Nov 2024LAS - IND
Read more Southwest reviews

This was a nicer flight - not fully booked and so we were able to spread out.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

All fine save for the abominable catering. Really gone downhill. We found it all inedible.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Boarding was slow the scanner broke mid through boarding and they had to manually do it

Average, boarding was ok, the eye scanner broken mid way through boarding they ahd to do it manually. Did not eat any food, Not even water was offered for free.

Boarding attendant was rude. Crew on the plan were more interested in talking amongst themselves and did not ask parentage if they needed anything or even walk down the isles.

Flight was ok with exception of the multiple delays. As with all Spirit flights, the sights are extremely uncomfortable and lack leg space. However, the price savings is the plus.

WiFi didn’t work despite paying for it. Crew was nice.

I upgraded my ticket at the ticket counter and was not informed of the huge bottleneck at TSA pre check. It took me over an hour to get through the line at this small airport and although I ran to the gate and reached it prior to scheduled departure, it had already pushed pack. I missed the flight. Spirit rebooked me on a flight to Orlando that evening, which would require me to then rent a car and drive to FLL. For scheduling reasons, I determined it be would better to rent a car in Pensacola and drive it to my destination in FLL. Spirit called me that evening and asked me if I was going to board the plane. I explained no, for scheduling reasons. The person apologized and said I would receive a refund, but I have not heard back. Certainly, I ought to be refunded the upgrade I paid for at the counter.

The staff from LAX to New Orleans were rude but the staff from New Orleans to LAX were nice!

Did what they needed to do. Brought us from point A to point B timely and without issue. Boarding through deplaning smooth.

Direct 2.5 hour flight good. Free snacks and coffee, water, or soft drinks not available...bad.

Atlanta airport gate area floor and nearly all seats disgusting. Spirit airlines crew fantastic!!

My first flight was moved 6 hours causing me to miss my meeting. The second was delayed about an hour and a half. Most of the crews apparently dont like their jobs or just working for Frontier. Only one flight attendant wasn"t snappy or rude.

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Book cheap flights from Chicago to Tuscany

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Chicago to Tuscany found on KAYAK in the last 72 hours.
12/8Sun
1 stopKLM
16h 52mMDW-FCO
12/24Tue
1 stopKLM
16h 21mFCO-MDW
$527
12/8Sun
1 stopKLM
16h 52mMDW-FCO
12/24Tue
1 stopKLM
16h 21mFCO-MDW
$528
12/8Sun
1 stopDelta
16h 52mMDW-FCO
12/24Tue
1 stopDelta
16h 21mFCO-MDW
$529
12/4Wed
1 stopDelta
16h 49mMDW-FCO
12/11Wed
1 stopDelta
16h 21mFCO-MDW
$536
12/4Wed
1 stopDelta
16h 49mMDW-FCO
12/10Tue
2 stopsDelta
19h 46mFCO-MDW
$541
1/21Tue
1 stopKLM
14h 46mMDW-FCO
1/31Fri
1 stopKLM
16h 35mFCO-MDW
$549
12/2Mon
1 stopAir France
12h 11mMDW-FCO
12/13Fri
1 stopAir France
16h 21mFCO-MDW
$561
2/16Sun
1 stopAir France
11h 49mMDW-FCO
2/24Mon
1 stopAir France
16h 35mFCO-MDW
$624
3/2Sun
1 stop
14h 46mMDW-FCO
3/6Thu
2 stops
17h 11mFCO-MDW
$873
12/10Tue
2 stops
13h 45mMDW-FLR
1/28Tue
2 stops
16h 46mFLR-MDW
$1,069

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Tuscany found on KAYAK in the last 72 hours.
1/15Wed
3 stops
31h 55mMDW-FCO
$303
1/6Mon
3 stops
31h 55mMDW-FCO
$319
1/19Sun
1 stopKLM
21h 30mMDW-FCO
$342
11/29Fri
3 stops
42h 45mMDW-FCO
$344
3/5Wed
3 stops
28h 14mMDW-FCO
$346
1/17Fri
2 stopsDelta
17h 56mMDW-FCO
$348
1/14Tue
2 stopsDelta
17h 24mMDW-FCO
$358
11/30Sat
1 stopKLM
12h 11mMDW-FCO
$452
5/1Thu
2 stopsAir France
19h 15mMDW-FCO
$610
3/10Mon
1 stopAir France
14h 25mMDW-FCO
$657

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Last minute flights from Midway to Tuscany

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Tuscany that are departing in the next 10 days.
11/25Mon
multi-stopDelta
14h 47mMDW-FCO
12/5Thu
multi-stopDelta
18h 31mFCO-MDW
$536
11/25Mon
multi-stopDelta
14h 47mMDW-FCO
12/5Thu
multi-stopDelta
18h 02mFCO-MDW
$580
11/24Sun
multi-stopAir France
12h 11mMDW-FCO
12/3Tue
multi-stopAir France
28h 47mFCO-MDW
$607
11/25Mon
multi-stopAir France
14h 47mMDW-FCO
12/4Wed
multi-stopAir France
16h 01mFCO-MDW
$696
11/24Sun
multi-stopAir France
19h 03mMDW-FCO
12/3Tue
multi-stopAir France
28h 47mFCO-MDW
$709
11/24Sun
multi-stopDelta
17h 59mMDW-FCO
12/3Tue
multi-stopDelta
17h 52mFCO-MDW
$716
11/24Sun
multi-stopKLM
12h 11mMDW-FCO
12/3Tue
multi-stopKLM
16h 01mFCO-MDW
$811
11/24Sun
multi-stopKLM
12h 11mMDW-FCO
12/3Tue
multi-stopKLM
16h 01mFCO-MDW
$835
11/25Mon
multi-stop
35h 16mMDW-FCO
12/1Sun
multi-stop
38h 34mFCO-MDW
$1,557
11/25Mon
multi-stop
35h 16mMDW-FCO
11/29Fri
multi-stop
35h 25mFCO-MDW
$1,570

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Everything you need to know for your flight from Midway to Tuscany

Information on your arrival and departure airports

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