3 weeks in Austria, Slovenia, Croatia- maybe Prague?

Plot out an itinerary - exactly what do you want to see? Plot cities on a Google map if you want to see which is the most logical direction to visit them in. List them out and then how many nights you have for each place.

I'd say, though, that your itinerary looks pretty rushed for only three weeks. I'd probably stick to Slovenia and Croatia for only three weeks, maybe add one Austrian city to start if it's easier to fly into from Chicago or something.

Here's (maybe) why Andrew said your itinerary looks rushed. 3 weeks sounds like a lot, but when you consider the realities on the ground, it's often not as much as you think.

Count nights. 2 nights (2N) gives you one full day to see a place. 3N = 2 days, etc. On average you use 1/2 day to change locations - pack, check out, get to the train station (longer to the airport), leave enough time to allow for traffic to find and board your train (much more if you're flying), then time to get from the station (more from the airport, even more if you have to check luggage) to your hotel, check in and leave your luggage. When you get to your new location, you need time to get oriented to the neighborhood, the buses/trams/metro, different language, different signage. Don't underestimate how easy it is to get confused or how long it can take to find a street name.

You can't count the day you arrive or the day you leave as a sightseeing day. Even if you land in the morning, it is likely to take you an hour or more to get through procedures at the airport, another hour to to get to your hotel. A non-stop flight to Munich is about 8.5 hours. That gives you maybe 4-5 quiet uninterrupted hours on the plane when you may or may not sleep. So you are likely to arrive sleep-deprived as well as jetlagged. Many people say their first day is really just a marathon to stay awake long enough to sleep through the night, not really appreciating much they see and do. Many are still in a haze on their second day and aren't up to full speed until the third day.

3 weeks of moving around with short stays can be exhausting and stressful, physically and mentally. Hiccups happen. And you need to consider things like laundry. Do you want to relax over lunch or snack and maximize your sightseeing? If you take it slowly, you will need more time in a place. If you try to see and do as much as you can, you may burn out, especially on a longish trip like you're planning.

I wouldn't make too many plans until I figured out what the open-jaw flight options are from Chicago and how you are going to get from place to place. Very useful websites are rome2rio.com for seeing the best options to get from A to B and bahn.com for train schedules. Also check if you rent a car in Slovenia whether you can drop it off in Croatia and if there are significant drop-off fees.

Thank you for the feedback, very helpful for novice travelers :) We've decided to save Prague for another trip; however, I'd like to keep Austria (Vienna, Salzburg, Hallstatt) then Slovenia and Croatia. Our travel options are early to mid August OR late Sept-early October. Does the scenery change between these two options? We have begun mapping out order of travel but there is a steep learning curve with the transportation schedules. Still wondering if it's best to fly into Munich with a travel order of Vienna-Salzburg-Hallstatt-Ljubljana to start or Salzburg-Hallstatt-Vienna-Ljubljana? Succinctly, what's the preferred route to Ljubljana considering transportation? Thank you!

Are you planning on spending any time in Munich, or just landing there and getting on a train to Austria? If you are not visiting Munich, your most efficient route would be to fly into Vienna and work your way from there through Salzburg (and Hallstatt), Ljubljana, then south through Croatia, flying home from Dubrovnik. Better still, fly from Dubrovnik to Zagreb for a couple of nights, then home from there. If you must fly into Munich, and aren’t staying there, I’d head straight to Salzburg. It’s a little over two hours by train from the Munich airport, with a change at the Munich main station. There’s lots of trains bound for Salzburg, and there should be no need to book ahead. That’s important in case your flight is delayed. To go from the Munich airport to Vienna will take about five hours. I wouldn’t want to do that after a long flight.

After Salzburg/Hallstatt, I’d go to Vienna, then to Ljubljana and Croatia. The train ride from Vienna to Ljubljana is a long one - six hours at least - but one way or another you’ll spend a similar total amount of time on the train if you start in Munich, regardless of the order.
I haven’t travelled between Vienna and Ljubljana, but I have taken the train between Salzburg and Ljubljana, and it is a very scenic ride. As for your question of timing, August will be crazy busy, especially on the Croatia leg of your trip. Late September will be quieter, but with a greater chance for less favourable weather. Also, if you arrive in Munich in late September they will be Oktoberfesting, so if you were planning on staying a night or two, hotels will be expensive- and probably full by now.

First write out a potential itinerary as a list - and indicate the nights you plan to stay in each. Then test it and see if it's realistic - and update it.

Start like this:

Salzburg (2 nights)
Hallstatt (1 night)
Vienna (2 nights)
Ljubljana (3 nights)
Zagreb (1 night)
Train to Zagreb, rent car
Plitvice Lakes (1 night)
Split (2 nights)
Korcula (2 nights)
Dubrovnik (3 nights)

That's 17 nights. Maybe you could add a night somewhere or even add somewhere else? Plot those places on a Google Map and see how much time to get between each place by driving, even if you will use the train in many places. Use Rome2Rio and bahn.com to check train and bus connections, see how much time it will really take and be realistic.

However - how many nights do you really have? If you have "three weeks" (fly out Friday, fly home Thursday three weeks later), that's 21 days...or 20 nights. But you lose a night flying in at the beginning, so only really 19 nights. Add nights if you want to if you want to do more than 19 nights, if you need it. But personally, if you are novice travelers, I would not make it too long.

I'd go to Croatia in September not August for sure! You might still have great weather but without the crowds and extra expense for high season prices. In fact, if at all possible, I'd start in Dubrovnik and go north - backwards - so increase the chances of good weather as you get into October.

I would not use Rome2Rio as a source of travel times or fares. I have found it to be off-base on many occasions. It is usually reliable in telling you whether planes, trains, and buses actually exist, but beyond that, I recommend other sources.

The Deutsche Bahn website is reliable for train schedules and is very easy to use. You probably won't find fall schedules yet. Some countries only have data loaded through about June 10, when the summer schedule begins. What you find for early June should be pretty close to what you'll actually experience in September or October.

For buses, you can keep drilling down on Rome2Rio, usually eventually finding the name of the appropriate bus company and perhaps a link to its website. If not, just Google "Bus Split to Dubrovnik" and click on likely-looking links.

BusCroatia seems to have relatively comprehensive information on Croatian buses, but I don't know that it's totally reliable. Bus schedules are more likely to change month-to-month than train schedules, and I couldn't help noticing that if I asked a Croatian tourist-office staffer about bus service in a different part of the country, he picked up his telephone to call the bus station in the other city rather than reaching for his computer keyboard. It's important always to verify bus schedules at the departure bus station ahead of time. Be careful about holidays, because there may be very little service then.

Check multi-city airfares from your origin into Munich and Vienna and out of Zagreb and Dubrovnik. See what looks financially viable. From my area Munich is often quite a bit cheaper than Vienna, but a modest extra expense is worth it if it saves you a day of vacation time.

I have found Rome2Rio to be extremely useful in trip planning. It saves me a lot of time in figuring out potential routings - especially when trying to flesh out an itinerary and see if it is practical.

However, I always verify every suggestion it offers for trains, buses, etc. and make sure they are valid. Rome2Rio links to the websites, usually, of the modes of transportation they recommend, and you can verify it yourself.

Sometimes Rome2Rio doesn't have the best method of connection between two places, but often it does. It's just one of several sources I use to figure out how to get between two places on a trip by public transportation.