June 2025 from Chicago
 

I am beginning to plan our first European vacation. Our family of four (youngest will be 19) will be traveling from Chicago in early June right after school gets out, planning on two weeks give or take a day or two with travel. Current family requests are Greece, Paris (least amount of time here), Italy, and possibly Austria. Our itinerary is completely flexible at this point and it looks like airfare from Chicago to London is our most reasonable option, but not sure about the return flight. Would rather not backtrack to London, but flying out of other areas is considerably more. Would really like to get our flights secured, but also wonder if I should hold off a little to see if rates come down at all. Wondering if we are better off doing round trip Chicago to London rather than multi-city for a different return flight.

Sounds like a wonderful family vacation! Should be fun to plan.

In my experience tracking flights from here (Chicago) to LHR or CDG, fares for June won't drop much. June is peak season; fares jump after the last week of May. If you can get a non-stop RT or non-stop multi-flight/open jaw from ORD to LHR, or ORD to Paris/CDG, LHR to ORD, for $800-850, I'd say you're doing really well. (I only fly non-stop b/c the timing serves me better. I'm still working and need to leave after a workday to maximize vacation; there's that cheap flight connecting flight through Iceland Air which many Chicagoans do, and maybe that appeals if you can build in a longer layover of a day or two.) You can put a flight tracker on google flights and monitor for 3 weeks to see how things are shaping up, but I think trying to sharpshoot a perfect day to book the lowest possible fare is really hard these days as everyone is making up for lost travel during covid.

In any case, be prepared for lodging in Paris and London to be very expensive. With 4 adults, plan on at least $400/night for a reasonable location/accommodation in a city.
Because you're traveling during a peak season, you should secure your cancelable hotels as quickly as possible. Apart-hotels (apartment-hotels) would be good, or apartment rentals. Or think connecting hotel rooms with (2) adult children.

The other thing: 14 days on the ground is quickly eaten up once you start adding in all the things you want to see in/around a city. So you may want to choose Paris-London, or just Italy, or just Greece.

My feeling is all England, or Paris-London (start in Paris, end in easier London.)

If all England, you can do RT to LHR and see SO MUCH in England/Scotland with no language barrier. Easy rail connections to York, Edinburgh, Bath/Cotswolds, or over to Cornwall/Land's End. Castles, museums, nature hikes, Jane Austen landscapes, HISTORY... so much for everyone in the family. You could possible rent a holliday cottage in some gorgeous landscape. https://www.nationaltrust.org.uk/holidays/cottages

Look at Eurostar for the easiest rail connections from London. You can visit Paris, Amsterdam, Brussels, and areas around there by rail. BUT... eurostar tickets get more expensive the longer you wait. (Eurostar is only booking through February 2025 now, so you'll want to start booking around late November/December to get the really cheap tickets.)

You're starting your children off with (hopefully) a love for travel. All of you can return on your own, so I think starting with an easier plan is the way to go. Have fun planning!

Also, RE: Paris, I just returned from there in May. If you're family is least-excited about the city, maybe just drop it. It is a beautiful city, but many places are very crowded. If enthusiasm is low, I'd strike it from the list.

Also: RE: England; keep in mind their Monday, May 26 bank holiday. So May 23-June 2 might have more British travelers enjoying their own country, too.

Thanks ChgoGal! The kids have already been to all 50 states, so they definitely have the travel bug. We have a former exchange student near Paris, so that's really the only reason it's on our list. I think it's a matter of wrapping my head around paying more for flights for simplicity and flexibility rather than just what is cheapest.

One thing worth reflecting on is the slowness of air travel compared to the speed of rail travel in Europe. Once you factor in the early start to an airport, the security the waiting the delays, the waiting for baggage, lines the transport to the city centre, flying short distances make no sense compared to hoping on a train.

I might look at London, Cambridge, York, Durham, Edinburgh as a trip. London is Europe's biggest city and a melting pot far more mixed than NY with lots going on. Cambridge is a small university town but with some glorious buildings, York is a walled city, Durham is just odd and Edinburgh is a small capital with a completely different vibe. seat61.com for general advice

I think you'd better skip Greece if you also want Paris or London. I think for the very first European trip, Paris-London is perfect ... with each, you'd be able to manage a day-trip outside the capital... and Eurostar such fun & so efficient! From center city to center city, with scenery going to/from the coastal entries. For budgeting accoms, I agree looking for 2 separate rooms rather that all-in-one (also, this avoids 4 people/1 bathroom).

So encouraging that you're thinking far in advance; and please do real homework on good websites, not just "eye candy." Also go to Chi's fab library & get an armful of guides; just browsing will give u insights. This Spring I was asked by relatives (couple in their 60s) for tips for their first-ever Europe trip London-Paris in 10 days. I groaned... but when they showed me their planned route, logistics, bookings & top priorities, I applauded. Efficient transport, great hotel locations, so all I had to do was add treats & hidden-gems. The more Planning, the more Pleasure.

Welcome to Fodors. Two weeks is a nice vacation -- but it really moves fast and you may have a lot less time for seeing/doing than you assume. You do say 2 weeks give or take a day or two. For discussion working with '2 weeks' i.e. exactly 14 days . . . that nets out to 11.5 days free on the ground in Europe. Then the first day or two at least some of your may be jet lagged. So maybe 9 days running on all cylinders. THEN you have to deduct another ½ to full day every time you move from one city to another.

That is not much time for more than 1 country, or maybe 2 or 3 cities within easy commute time of each other. Certainly not enough time for Greece and Austria and Italy and Paris and London. It isn't even enough time for two whole countries.

Adding a day or two will help a bit bit a 16 day trip still only net 13.5 days on the ground.

Re flying in to London - that only makes sense IF you plan on visiting the UK. Otherwise, any $$ saved on the airfares will be eaten up plus with getting to the other places on your wish list and back.

I'd maybe re-think this and do something like 1) JUST London, Paris and maybe one other short stay in a more rural part of England or France; or JUST Austria and a couple of days in Paris to see the friend; or JUST Italy + a couple of days in Paris (and you'd really only have time for a couple of places in Italy -- Rome and Naples, or Florence and Venice, or some other combo)

Two weeks and five countries? I resign from any advice about that;

I agree with dropping Paris. I will also add that moving around a family of four can be time consuming and expensive. If you are price sensitive, then consider visiting fewer 'countries' but flying directly to where you want to be. Flying into one airport and out of another means less waste, easier and happier traveling.

I'm not sure how Greece, Paris, Austria and Italy would be best served by a flight to London. While it may be cheaper, your transfer costs to other places eat that up quickly.

"Would rather not backtrack to London, but flying out of other areas is considerably more."

Did you search as two one-way flights on possibly two different airlines? You need to search "multi-city" flights on one airline (which would also include partner airlines). One-way fares are almost always the most expensive option.

Since this is your first European vacation, I suggest you keep the logistics simple, pare down the destinations, travel in a smaller geographic area overall, use trains if/where possible, etc. If you were to keep all four of the requested destinations in the itinerary, it would result in a big-cities-only trip with at least 3 days lost to transfers.

Since London isn't on your list of places to see, I would aim to fly to someplace you actually want to visit. Yes, flights to London may be cheaper but you then have to figure out the cost of transportation to get to where you want to be and the cost of backtracking. Two weeks is not a lot of time but limiting your trip to Greece and Italy and not wasting days traveling to and from a location you don't wish to visit, should work well.

You seem to like the idea of Chicago to London ("most reasonable"), but then don't seem to want any time in England. I infer from that that you only view that as "cheaper than landing in Paris". Are you forgetting about the time and cost to go from London to Paris? Time carved out of a 2 week span?

Been to all 50 states? Sounds like my brother-in-law, a now-retired schoolteacher, who was somewhat proud of having taken his family to all the lower 48 states during summer vacations. Yet he had NOT traveled to some (to me) interesting sites in some of those states. In other words, what's the point of saying you've been to Wyoming, if you didn't get off the expressway to stop in Yellowstone? or Utah, without Bryce? or out of the car whatsoever, going thru Iowa?

To me, the purpose of a trip to Europe is to experience, to absorb, to imbibe the local culture. You CANNOT do this from a car window, or a train window, or from behind the screen of an iPhone. You must talk with local people. and that takes time.

If all you want to accomplish is to get as many country stamps on your passport as possible in two weeks, land in Amsterdam, hire a car, and get stamped for France, Belgium, Netherlands, Germany and Luxembourg in a short distance.

I'm also wondering what the family's interests are: why Greece, but not Paris? why Austria, but not Germany? why Italy, but not France?
Aside from that, I question the point of seeing the exchange student (taking 15% {two days out of the 14} of your time in Europe, to the exclusion of so many other sites and experiences. Nice to do, if you had the time, yes, but you don't. You could "face-time" her at far less expense.

Flights
 

I recommend direct flights, especially during peak travel season. It is a lot less hassle and you spend less time in airports. You don't have to worry about connections and getting stuck in an airport either. My wife and I were booked on a flight from Genoa to Amsterdam in May 2022. The plane got delayed and had to go around some rough weather, and we didn't make our connection. KLM did put us up in a hotel at the airport, but I had to complain to get that.

To me it is worth the money to book the return flight from wherever it is you end up instead of backtracking - assuming you can get a direct flight.

Another thing I would recommend is getting a phone plan before you go. We use Verizon and I got a plan with them. Not as expensive as it was a couple of years ago. And make sure you know your PIN if you have one.