Need advice on how to book my air bnb

I don't know where you are travelling from, but is it possible to do this as an "open jaw" trip. Flying into Amsterdam and out of Paris, or vice-versa? That would save you doubling back.

We're leaving from Chicago. That would work out better.

It depends on whether you want to keep the Amsterdam lodging and pay for days you'll be away from Amsterdam.

Just book each night as you need. I would start in Amsterdam, hit Brussels, then Paris and come home from Paris. More efficient use of time and travel and probably cheaper. Do you have ten days including travel or ten nights excluding travel. I would do four nights in Amsterdam, 2 nights in Brussels, and four nights in Paris. Nice trip - relaxing schedule, min travel time.

I agree - fly into Amsterdam and out of Paris (or vice versa). Don't book 2 one-way tickets, use the search for "multi-city" flights and it should cost about the same as a round trip. Especially when you consider the cost of getting back to AMS after Paris.

So book an airbnb in Amsterdam and one in Paris. Leave from Paris.

If you have to go in and out of Amsterdam for some reason, consider arriving in Amsterdam, get a train to Paris THAT DAY, spend 2-4 nights there, then go back to Amsterdam for the rest of your time. I personally have a rule of thumb that I like to end my trip in the city I leave from. Otherwise you might need to spend a night near the airport, and time is better spent in the destination. For example, you could go Amsterdam for 6 nights, Paris for 3, then back to Amsterdam for 1 (so you can get to your flight on time). But that's annoying.

Would I need 2 extra days off for flight travel?

Count the day you fly out of Chicago as Day 1/Night 1 as it is an overnight flight. The day you land in AMS is Day 2. Now you start plotting your nights and where you will sleep. So:

Day 2/Night 2 - Arrive AMS, find your lodging, clean up, have lunch, take a walk, try not to nap, have dinner, sleep like the dead.

Day3/Night 3 - Amsterdam

Day 4/Night 4 - Amsterdam or day trip in The Netherlands

Day 5 Take the train to Brussels. Night 5 sleep in Brussels

Day 6/Night 6 - Brussels

Day 7 Take the train to Paris. Night 7 sleep in Paris

Day 8/Night 8 - Paris

Day 9/Night 9 - Paris

Day 10 - Fly home. You will arrive the same day you leave Europe

This is a very fast-paced trip, IMO. Note you really only have 8 full days on the ground as two days are flying into and out of Europe. You would need three places to stay. Since all are short stays, an AirBnB or other apartment rental is not really optimal. A B&B or hotel would be more efficient and offer you some assistance as well.

Well a flight from Chicago usually leaves in the afternoon/evening and arrives in Europe sometime the next morning - overnight flight. Sometimes a direct flight, sometimes there's a stop. Lets say direct - the United flight I know of leaves around 6PM (and arrives in AMS at 8AM). So you need to be to the Chicago airport 3 hours before the flight leaves and you don't get to Europe until the next morning. Only you can say what that means for your work schedule/vacation time. But it is one night that you will spend on a plane, not in Amsterdam or Paris.

Then return flights usually leave Europe in the morning to early afternoon and arrive in the evening the same day. So if you leave at 12 you get in at 4PM or so. Magic of timezones. That is a day that you spend in a plane, not in Amsterdam.

It's worth noting that different airports have different fees (taxes) that they apply, which is baked in to your ticket cost (the airport taxes are applied when you depart from a city, not when you arrive there). Of your three cities, Paris has the highest airport taxes, and I think Brussels probably has the lowest. So, by all means, do shop around for your best ticket price (I'd hasten to add that you should also consider other factors, such as comfortable travel times/layovers, efficient use of your time, seat comfort, etc. - be smart first, it's not only about the price). You probably would save a few bucks by NOT flying out of Paris (flying in to Paris won't cost extra). Many people find the main Paris airport a bit hectic and inefficient - personally I'd rather experience that on arrival than on departure.

Some other considerations I'd suggest...

1. Your trip is very short - too short for a trip to Europe, IMHO (unless you've been there before and you are experienced and will be very efficient, but that's not you). I'd urge you to try hard to find at least a few more days if there's any way you can - otherwise you are not getting the most from your money spent getting there and back. If you say your trip is "10 days" that means you have about 7 days of usable time in Europe (you lose 1-2 days getting there and 1 day getting back, and your first day or two there will be a bit confusing, foggy and jet-lagged). With less than a week of days when you're feeling 100%, you need to minimize or eliminate moving from city to city. Forget going "back" to a place you just left, that's crazy.

2. As noted above, do NOT fly into city A, go to City B, then return to City A. Incredibly wasteful of both money, and the other commodity that you are short on - time. Do open jaws, fly into City A, train to City B, then train to City C and fly home from there. Once on the ground, take trains - Paris/Amsterdam/all-of-Belgium are close together and I see no reason to fly (it would take longer).

3. For many people, Brussels is a bit of a disappointment compared to other major European capitals. If I had just a day to spend in Belgium, I'd spend it in Bruges.

4. If it were me, I'd suggest this order: Fly into Paris, spend a few days there in Paris. Train to Bruges, overnight in Bruges. Skip Brussels. Train to Amsterdam, spend a few days there in Amsterdam. Fly home from Amsterdam.

Worry about booking your accommodations later. First, plan your itinerary, book your flights, then book accommodations.

What time of the year are you going?

Hope some of this helps.

Thanks everyone for your help!! We're going late September of next year. Our main reason for going is to visit a friend in Amsterdam so we might be able to stay a few nights with him. I think we'll fly into Paris first for 2 nights and spend the rest of our time in Amsterdam.

For Amsterdam apartment lodging, you should look at amsterdam.citymundo.com- they have postings for rooms, apartments and houseboats. They are very responsive to any email questions. I also looked at Tripadvisor listings for apartment. I liked the way you can communicate with the apartment owners.