Rome, Florence, Venice in 8 days???

Why not go to Venice at least as a day trip from Florence, since you'll be so close? It sounds like you want to see it and I definitely think it's worth a day. What time of year are you planning to go-- will there be long daylight hours?

Of course you can't see everything in a week but it sounds reasonable since the cities aren't that far apart by train. I wouldn't waste time renting a car when the trains run all the time and are pretty easy to use. Will you do open jaw flights, fly in to Rome and out of Florence or Venice?

Have you ever been to a country where they don't speak English? I ask because it is completely unnecessary to speak Italian for the trip you are proposing. As our host writes in his travel books, it is appreciated if you learn the six or eight courtesy-words, but you are simply not going to be lost or starved without Italian. Do you normally travel independently?

I agree that you need to find an open-jaw flight combination, with your limited time. Otherwise you'll lose a day backtracking and getting to the airport. That may be even more true with Chicago, although I'm used to flying from NYC and don't know your likely connections. I will note that we have done very well (in our case, for price rather than time ... ) with two-segment flights to Europe that are on the same airline. (Lufthansa, in our case.) Since your hotel is never ready at 9AM, there is little downside to arriving at noon instead!

"We have heard that Venice is dirty." Well, I've heard that Chicago is "dangerous". But I've been there three times, and hope to go again soon. Venice is also, unique, and endangered. I agree that you should go, even as a daytrip from Florence. Whether you sleep in Venice depends on your interests in Rensaissance art in Florence, and your sleeping and travel preferences.

With your time schedule, you might be better off with full-service hotels than real B&B's. For example, you might want a bag check for last-day sightseeing, or very late arrival. With your SEVERELY limited time, it's silly to talk about "experiencing local culture", if that's what you meant. And if you meant AirBnB, which I deplore, do you really want to spend your limited time washing dishes (and missing local cooking?)

Your flight home from Italy will usually get you back to the states on the same day, unless you have an overnight trip in store after you get back to Chicago.

Agree that renting a car isn't necessary, especially on your first trip to Italy. Italians are way better at English than Americans are at Italian so not speaking Italian isn't really a problem for most visitors.

The one thing I've learned on this forum is that people feel about their favorite hotels in Europe the way Texans feel about football teams. "My" Hotel Alessandra in Florence isn't a B&B, but a good breakfast is included, it's in a great location, with kind staff. The stairs are only a problem if you have a problem with stairs.

http://www.hotelalessandra.com/

Another thing, it's hard to avoid touristy destinations in Rome, Florence, Venice, but we really enjoyed our Chianti wine tour with Tuscan Trails in 2014. Check them out on TripAdvisor. This small group tour will get you away from the crowds and into the countryside with wine tastings at two wineries. A great lunch (with wine) is included. It's not cheap, but a great value for money.

http://tuscantrails.com/

2-nts Venice
3-nts Florence
3-nts Rome

This itinerary should suffice. Venice is unique however, its pretty easy to hit the highlights within a day, give it 2-nts, soak up what you can. Evenings in Italy are romantic and much more enjoyable when the tourist crowds have receded. 3 nights each in Florence and Rome should be enough for you to hit the major destinations while wetting your appetite for a return trip.

Sat - Arrive Venice - 2 nights
Sun - Venice highlights
Mon - Train to Florence - 2 nights
Tue - Florence highlights
Wed - Train to Rome - 3 nights
Thu - Rome highlights
Fri - St Peters & Vatican museums
Sat - Depart Rome

Book the open-jaw tickets to save yourself from backtracking at the end of your trip. We did a similar trip this past summer. We arrived in Rome at 9:00 (having flown in after spending 2 days in Amsterdam, so we were already adjusted to the time change). We spent 3 nights each in Rome and Florence, and 2 nights in Venice, and flew home from Venice. It was a whirlwind of a trip but we really were able to see everything we wanted in that timeframe.

Consider flying into Venice, skipping Florence, and flying home from Rome. You really don't have a lot of time and I'm sure you don't want to spend anymore time in transit from place to place than needed. Believe me, it always takes more time to change your base of operations than one plans. Venice is not dirty. It is beautiful and unlike any other city we've visited. By splitting the time between Venice and Rome you can hit the high points of those cities and still have time for day trips to nearby areas. Just something to consider.

I've never used this forum before but you are all so kind with your advice and suggestions. The itinerary suggestions is just what I needed and the Hotel Alessandra is jaw dropping and reasonably priced. We looked at a cut B and B on line in Rome next to the Basilica for $50 a night. This isn't necessarily a budget trip but it got a 4.0 trip advisor and a TON of 5 stars. The Tuscan Trails looks amazing too and exactly what I am looking for. A 5.0 Trip Advisor rating is crazy and everyone had amazing things to say.

I invite any other specific favorite place suggestions and have 1 more question. If there is no car rental, how do you get around? Uber and Cab? Bus? Subway? For example, How do we get from Hotel Alessandra Hotel to Tuscan Trails? Are yo picked up from the Tour?

Again, thank you all for helping us form this trip and feel comfortable with traveling in a foreign place and embracing these experiences.

David in Brisbane has given you a very good itinerary for your time constraints. Of course, you could add or subtract a day to a place (eg, 3 nights in Florence and 2 in Rome), depending on your interests. Don't cut your Venice time, as the day of arrival is often a jet-lagged haze.

Just a few points that will help you as a first timer.

1) You definitely want open jaw (multi city) flights, into Venice and out of Rome. On such a short trip, you don't have time to backtrack. To find these flights, use the "multi city" or "multiple destinations" function of Kayak, Google Flights, airline websites, etc.

2) You want to follow David's order, starting in Venice and ending in Rome, rather than the other way around. Flights back to the US leave early (sometimes shockingly so, if they have to connect in Europe first). Getting to Rome's airport early is not hard or too expensive (a taxi costs €48 and takes about 35 minutes). Getting to Venice's airport early takes well over an hour, unless you spring for a very expensive water taxi (way over €100).

3) You say you would leave Italy Saturday and get back Sunday. Unless you have a very unusual flight itinerary, flights back from Europe get to the US on the same day - albeit potentially very late. So, you should be able to leave Sunday and get back Sunday night, particularly from Rome which will have a lot of options back to ORD (including nonstops on United, American, and Alitalia).

However, flights from the US land in Europe the morning after they leave, so if you fly out of Chicago on Friday night, you get to Venice on Saturday; just how late on Saturday depends on what connections you get. There are no nonstops from ORD to VCE, but you will have numerous options with only one change.

4) As for Venice being dirty, well, it's not Vancouver. But then, none of Italy is scrubbed or sanitized; the big cities are big cities. Coming from Chicago, you will know how to look beneath the surface dirt. Also, graffiti is not a sign of a "bad area" as it can be in the US.

and have 1 more question. If there is no car rental, how do you get around? Uber and Cab? Bus? Subway? For example, How do we get from Hotel Alessandra Hotel to Tuscan Trails? Are yo picked up from the Tour?

Two out of the three cities you want to visit have wonderful transportation systems. When you arrive in Venice you can take a shuttle bus or water taxi to the historic center. From there you can easily walk or take the vaporetto boats. When you arrive at the Florence train station you can walk or take a cab to the very walkable and compact city center. When you go on an organized tour they will have a centralized meeting point or pick you up at your hotel. When you arrive at the train station in Rome you can again take a cab, the metro or walk to your hotel depending on its location. Rome is the most spread out but it has buses, taxis and a metro system. It is also a joy to walk.

$50 a night for two people in central Rome is--how shall I put this?--pretty shocking. Are you sure that room has a private (en suite) bath? If you're traveling during what could be hot weather, does it have air conditioning? I paid considerably more than that in May 2015 for a tiny, closet-sized single in Trastevere. Just be sure you know what you're getting.

The historic center of Florence is quite walkable, and the Hotel Alessandra seems to be well-located not far from the the Ponte Vecchio and the railway station (in opposite directions). Depending on what sights you want to see, you might not need any form of transportation in Florence other than your own feet. I don't know what Tuscan Trails' arrangements are for customer pick-up; that information should be available on its website. In general, though, I would not be happy about a big-bus tour (if that's what they use) that picks up tourists at their individual hotels, because that could chew up a huge amount of the tour time.

Venice has no streets, so transportation there is on foot or by vaporetto (water bus). Individual vaporetto tickets are extremely costly, so it usually works best to buy a pass that fits the number of days you will be in the city. However, if you don't care to see (or don't have time for) the islands of Torcello, Burano and Murano, it's conceivable that you might end up walking just about everywhere. Do take at least one vaporetto trip down the Grand Canal, though.

Rome has a subway system and lots of buses. Certainly there are also taxis; I don't know anything about Uber. Since your trip is short, you probably will want to use some form of transportation to get around on occasion, but walking is a great opportunity to experience more of the city. If all you do is line up at museums and walk around inside, zipping from sight to sight by taxi, how much of the city will you really experience?

Here is where it can be very helpful to stay in a hotel rather than a more casual form of accommodation. Your hotel will normally be able to tell you where to pick up buses to go to the top tourist sights. But you can get this information ahead of time from a guidebook (in the case of the subway, at least), by Googling, or by asking here.

You will need a guidebook for planning. Especially on such a short trip it's essential to know what days museums and other attractions are closed, which evenings (if any) they have extended hours, etc.

$50 for a hotel near which Basilica? I usually stay in a family-owned hotel near the Colosseum for about €75 single with breakfast. That is a bargain and it has all amenities, including a/c.

In Firenze, you can walk everywhere, and as posted above, central Venezia is good for walking, too (albeit over a lot of little bridges).

To get around we walk, taxi, subway, bus, train, etc. Public transportation in Europe is great!

I would not call Venice dirty or at least any more than any other large city. Venice is really old and due to how it was constructed over water, a maintenance nightmare. So I would call it crumbly, but that is also part of the charm. It is my favorite city and any time I can fit it into a trip I will try to go, there is no place else quite like it!

I'll just emphasize two points other posters made above:

1) You need to get a guidebook as soon as possible. It will have all kinds of information, not only about things you've asked liked getting around, but also about things you didn't even think to ask yet.

I think Rick Steves Italy is the best guide for a first time visitor, but don't hesitate to raid your library to get others, to get more than one point of view. However, in a short visit, you won't even be able to cover all of what Rick describes, much less "get off the beaten path." Don't worry - Venice, Florence, and Rome are called "The Big Three" for a reason. You'll have a great, if busy, trip.

2) Fifty dollars for a room of any kind in central Rome, other than a dorm bed in a hostel, is so low it's suspicious. If someone advertised a "great place to stay in Chicago, right next to Water Tower Place, for $50 per night," wouldn't you be wary? Treat this the same. I paid €55 per night for a single in a B&B in Palermo (it would have been €65 for two); Rome is considerably more expensive.

For me one of the great joys of visiting Italian cities is shedding a car! Take trains between them. Venice and Florence are so so walkable and many of the sites in Rome are too. Also, Rome has Uber in addition to taxis. I recommend Arco dei Tolomei B&B in the Trastevere section of Rome which is reasonably priced (around $165) a night and close to almost everything. It is in the Rick Steves guidebook and you can see pictures on Trip Advisor.