Belgium, Amsterdam, Berlin

I would take some time away from Brugge and add to Amsterdam for day trips.

To some of your questions:
1. The Intercity service from Brugge (change in Brussels or Antwerp) to Amsterdam takes some 45 to 60 mins longer than the high-speed Thalys. The ticket prices for the Intercity depend on the day of the week, but are fixed and tickets are valid for all Intercity trains running that day, making them more flexible to use. Consult the train planner at the site of NMBS/SNCB (the Belgian railways)
2. Amsterdam to Berlin should be bought in advance. Bought last minute they can cost EUR 130 or more, while the same train can be as cheap as EUR 39,90 when bought two or three months in advance. The restraint is that these tickets are for a specific train (day and hour) and are not refundable. It is not the most scenic route in Europe, but it is a relaxing ride. Schedule and prices at the site of Bahn.de (the German railways).
3. Seniors (65+) can have their day trips at a bargain in Belgium: return tickets to all destinations for a mere EUR 6,80, which makes them cheaper than the Rail Pass. The only restraint being travelling after 09:00 on weekdays, missing the rush hour (see this page at the NMBS/SNCB site).

I would take some time away from Brugge and add to Amsterdam for day
trips.

I will gently disagree as the OP has already been to Amsterdam. We LOVED Brugge, stayed 4 nights (one day trip to Gent) and could have stayed longer. We also did as the the OP is thinking and stayed in Brussels on our arrival day; train to Brugge the next day. We did stay in Antwerp for 3 nights versus day-trip it from Brugge. Belgium was sort of a revelation for us as we enjoyed it FAR more than we'd expected, and more than Amsterdam, to be frank.

“Maybe one night in Brussels”

Brussels is worthwhile to visit as a day trip but spending the first night “to get over jet lag” is not needed in my opinion as Bruges is only another hour away. If you want your home base in Belgium to be Bruges, I would suggest making your way to Bruges that first night (assuming you fly into Brussels).

“What city would be best to depart from Belgium to Amsterdam?”

The high speed Thayls line will leave from Brussels Midi train station (or Antwerp). If you have a set day/time you plan on heading to Amsterdam, going to the Thayls site and buying the ABS (any Belgian station) ticket could be the way to go if you book it ahead of time.

“Would it be better to fly from Chicago into Amsterdam and then take a train to Belgium and then a train from Belgium (Brussels?) to Berlin?”

That is based on the open jaw flight deals you have from O'Hare. I personally find AMS airport so much easier to navigate to compared to Brussels airport but the airfare is the main driver on this.

Have fun.

If you have a good price to fly into BRU, I don't see why your would fly into a city you've seen already and specifically said you are not going to sleep in. I don't consider Amsterdam and Brussels to be "the same place." Also, we spent two weeks driving from Venlo to Amsterdam! A week is not too long for Berlin. I encourage your daytrips in Belgium. This is easily and cheaply done by train.

You might sleep a night in Brussels if you have a specific desire to see one of the three to five exceptional art museums, or the other museums and sights of Brussels. But it's the least interesting visit (opinion) on your list.

I would just throw out that it's easy and cheap to get to Cologne from Brussels (and thus from Bruges.) If you have any desire, two nights there might be a treat. I also prefer to sleep several nights in one place. But Cologne is exceptionally walkable, and has many hotels near the Hauptbahnhof, which is walkable to 80% of the sights. (I stayed almost across the street, at the soul-less but comfortable Hilton.)

You might sleep a night in Brussels if you have a specific desire to
see one of the three to five exceptional art museums, or the other
museums and sights of Brussels

Right. That's why we stayed that one night/partial day: wanted a walkabout to see the cathedral, Grand Place and general look at that part of the city. True, though, that you can be in Bruges in an hour if choosing to just go onward upon arrival.

If the price of flights to Brussels is the same as for Amsterdam, then Belgium-Amsterdam-Berlin is the most logical order, as there are direct trains from Amsterdam to Berlin whereas you need to change between Brussels and Berlin (same duration, though).

Thank you for the sage advice. These comments have been very helpful.

Hey travelers,
We have booked our flights to Brussels with a return from Berlin and have booked a room in Bruges for 7 nights (We may only stay 6). Thanks for the advice on the train from the Brussels airport direct to Bruges, we arrive at 9:00 am so that will be good. We will plan on seeing Brussels, Antwerp and maybe Ghent on day trips.

We may just wait until we arrive in Belgium and then book a train from probably Antwerp to Amsterdam (Is that easier than taking train to Brussels? Do they connect in the same train station?) .... it is a relatively short trip, so it may not matter much to us whether it is a high speed train or a local.

We will be staying 3-4 nights in Amsterdam.

I will take the advice and book a train in advance from Amsterdam to Berlin. Using the Bahn website was kind of confusing, not being familiar with the either the train system or the way you navigate the website. I have looked at the DB navigator ap and am not clear about the terminology. thereare several trains throughout the day all at the same price. When it says "changes", does that mean you actually change trains and seats and have to carry your luggage from train to train? Are there any other agencies or websites that are easier to use? Does the Rick Steves organization book train travel?

As for sightseeing in Belgium, we plan on using the Rick Steves guidebooks and audio guide. Are there any particular cities or locations that a private or group tour is recommended?

Using the Bahn website was kind of confusing
You could see whether you find Loco2 or Trainline (both trusted ticket agents, offering exactly the same tickets as the Bahn) easier to handle.
A change of trains is indeed a change of trains, which means moving yourself and your luggage to the connecting train. On the Amsterdam to Berlin route that will be in Hannover, where you probably only have to cross the platform to the other track. Assuming you'll have seat reservation, make sure you stand at the platform section where your carriage will stop, using the information panels (Wagenstandanzeiger, Train composition, or similar wordings) on the platform.

There are direct trains (=one-seat-rides) between Amsterdam and Berlin; I'd prioritize those over any route with a change of train even if changing trains saves 15 minutes. Of course, if there is a large price difference, then changing trains is just a minor hassle.

Sounds like your plans are coming together - it makes sense to stay in one place to minimize hotel reservations. There are many opinions on the length of stays in Bruges vs Ghent. Should you find seven days is too long in Bruges, I can recommend highly the Hotel Carlton in Ghent. The proprietors are brothers who know the area Ghent and Bruges and can give you tips that you were quite helpful to us. Their establishment is easy walking distance from the train station and bus service is just three blocks away. Ghent is more centrally located between Brussels, Antwerp and Ghent.
If you decide to try a couple of days in Amsterdam, consider staying outside the city proper. It is very easy to get around; we found a house to rent in Zandaam which worked out well for us and was reasonably priced. Consider a reservation at Martine's Table for dinner in Amsterdam.

Have fun!

a train from probably Antwerp to Amsterdam
Antwerpen Centraal is a complicated station with three levels. Your train from Brugge or Gent will arrive at the highest (3rd) level, while your train to Amsterdam leaves from the lowest, connected by a series of escalators.
Changing trains at Brussel Zuid/Bruxelles Midi (same station with the Dutch and French names) is easier.

Tonfronleiden,
Thanks for the train advice. I am looking on the Rick Steves train ticket website, which is very easy to use, and found tickets from Brugge to Amsterdam. The transfer in Brussels is 22 minutes. Is that a reasonable time to allow for a transfer?

Not to disagree with tonfromleiden, who knows more about the low countries than I know about my own hometown, but if you have a choice of taking a train from Brussels or from Antwerp, I strongly recommend Antwerp. It's absolutely one of the most beautiful train stations in the world. And it's not so complicated that you will be unable to find your train. Try to get a few minutes to look around, and go outside to see the building from a short walk away,

Thank you for the train advice. We will be doing a day trip to Antwerp, so we will see the station then. We are opting for the Amsterdam train via Brussels because of the transfer, which is onlt 7 minutes and then having to deal with the various levels that were described.

I am looking at the Brugge to Brussels to Amsterdam train ticket fine print and am wondering if this is info that is of need to know importance:

Does anybody know what the following means with respect to "diablo", "ABS", "Brussels Midi and Brussels Airport stations."?

From BRUGGE To BRUXELLES MIDI
Train 2810 - Reservation not included
2 x B - 2nd Cl ABS Connection

The schedule information provided is only a suggested itinerary. You will be able to use your ABS ticket to/from Brussels Midi Station to travel to/from Any Belgian Station (ABS) within a restricted time period. A separate ticket for this portion of travel will not be printed. Travel to/from Any Belgian Station (ABS) is covered under the ticket to/from Brussels Midi station. ABS tickets are not valid on Thalys trains. Please refer to the conditions provided with your ticket.
From BRUXELLES MIDI To AMSTERDAM CS
Thalys 9327 - Reservation included

2 x 2nd Cl Leisure 3 ABS Adult
Subject to availability - Includes ticket for domestic Belgian (SNCB) segment that is valid for 24 hours before/after arrival in Bruxelles. If domestic Belgian (SNCB) segment is between Antwerp/Brussels<>Brussels Airport, a fee is payable locally. Print at Station (TOD) tickets, when available, can only be retrieved from French stations. Please select your ticketing method accordingly.

ABS fares do not include Diabolo Fee for travel between Brussels Midi and Brussels Airport stations. This fee is payable at the SNCB counter.

This all simply means that BRU airport, in which you have no interest or desire, is not part of the Brussels urban zone (3 stations.) You don’t need ABS to move from Midi/Zuid to Centraal Station (for Grand Place or Museums or Hotels, it’s included with all Eurostar/Thalys tix. All local tickets to Brussels cover three non-airport stations.

But ABS can take you to or from Bruges (or any Belgian station) the day of your trip, without having to wait in line and buy an unreserved local train ticket. This covers about 6 to 8 trains an hour to Bruges, just as an example.

»Diabolo« is the ticket for the train between Brussels Airport (locally known as Zaventem) and one of the stations in Brussels proper.
Whatever train you take from Brussels to Amsterdam, have some cushion time - half an hour or so - for your connection from Brugge. Nothing is so nerve-wracking as a short connection time at an unknown station, while your first train is slowly building up a delay. Your ticket will be valid for all trains between Brugge and Brussels.

Hi folks,
We are back from our trip and i wpould like to provide some feedback to those who provided us with advice.

Thank you to all advisors, we had a great trip.

We stayed in Bruges for six nights and it was a very good choice.... definitely a vacation mode. We stayed at a Rick Steves recommended B&B, Amaryllis, and it was very nice and a good value. We did the walking tours, saw some great art, went to the Dali Museum, which was surprisingly good, a boat ride, and ate chockolat, nugget and some good meals. Bistro den Amand was particularly excellent. We took one day trip to Brussels, did the RS walking tour and went to the Royal Museum of Art and the Magrite Museum and had a great dinner at Chez Leon. We were also able to catch a free full day classical music extravaganza at the Concert Hall, which was produced by the owner of the B&B that we stayed in. That was a treat.

The advice about taking a train from the Airport to Bruges was very good advice. We arrived at the airport at 9:00 am and it was good to go direct to a hotel in Bruges and get over out jet lag without any additional travel stress or moving. If I would do anything different, I would have stayed overnight in Brussels on the last day and not have to deal with the travel to Brussels to catch a train to Amsterdam in the morning of our departure.

In hindsight, we should have skipped going to Amsterdam for 3 nights, two full days. Not really enough time for a meaningful experience. We had been there previously and had already seen the Rik and van Gogh Museums; this time we went to the Stedelijk Modern Museum. We walked the walking tour, went to the flea market and found some decent restaurants on Restaurant row (we stayed at the RS choice Alexander Hotel, which was near Liedseplein) which was close to where we were staying. Getting high is no longer a priority!

Over the years, we have found that RS recommended restaurants and hotels are always a good value, hunting for a RS recommended restaurant, while often fun, is sometimes too far to go and takes too long.

The train to Berlin was kind of a nightmare. We had to get off the train because of some kind of disturbance on the track and had to take four trains because we missed the scheduled train in Hannover. So much for the 1st class upgrade. I guess German trains no longer run like clockwork.

I will provide feedback on Berlin on another thread.

Thanks to all for your advice.