Travel Forums North America Chicago-Toronto-Boston-NYC

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1. Posted by BCNguy (First Time Poster 1 posts) 12y Star this if you like it!

Hi everyone!

I've planned to drive from Chicago to New York City going through Toronto and Boston at the end of July. I have several questions, and your help will be greatly appreciated:

1) What places do you recommend seeing on my route? I plan to travel from Chicago to Toronto, spending the night mid-way, then continuing to Toronto, spending one night there at a nice hotel (any suggestions?), then spend the next night somewhere half-way between Toronto and Boston, and finally go to NYC. About these... "in-between" places... What would you suggest seeing? I'm mainly going to see architecture, but any typical or specially nice places to see will be most welcome! :)
2) If I rent a car in Chicago, will I be able to cross the border to Toronto with it?
3) I live in Barcelona, and I'll be flying from Barcelona to New York. Once there, I'll fly to Chicago. I'd like to get a one-way ticket, but these fares are much more expensive than a return fare. Is there any problem in the US if I get a return ticket and don't use the return part of the ticket? I'm just curious, as I wouldn't like to be stopped at the border with authorities thinking I'm some sort of terrorist or something...

Your help is greatly appreciated!!

Best regards


2. Posted by GregW (Travel Guru 2635 posts) 12y Star this if you like it!

There isn't much half-way between Chicago and Toronto. Half-way would put you in Michigan. Perhaps you could think about Ann Arbour - it's supposedly a nice little college town. I wouldn't bother with Detroit. If you like gambling, you could think about going all the way to Windsor and hitting the casinos there.

What's your budget for a Toronto hotel? There are lots of nice hotels.

Half-way between Toronto and Boston - you could stay in Montreal for a night. Montreal is an interesting city, kind of the love child between a North American city and a European city.

You should be able to rent a car and cross the border, but make sure you let them know that you are doing that. Are you planning on driving back to Chicago, or dropping the car in New York. One way rentals can be very expensive.

For the return ticket, do you mean that you'll buy a ticket from NYC-Chicago return, and not use the Chicago-NYC portion of the ticket? If so, while technically not allowed, there is little the airline can do about it. If pressed by the airline, just say that your plans "changed" and you didn't need the return part of the flight.

If, however, you mean you want to buy a Barcelona-NYC-Chicago return ticket, and only use the NYC-Barcelona leg on the way back, then that isn't possible. Once you don't show up for your Chicago flight, the entire rest of the ticket will be cancelled.


3. Posted by karol4u (Inactive 5 posts) 12y Star this if you like it!

Being that I've been to Toronto a few times I can help you a bit with that end of your trip. I would recommend staying downtown at Sutton Place Hotel, it is a very classy hotel. Old City Hall is a great place to visit for it's architecture, and a must see is the CN tower. Down the road from there is Skydome where the MLB pros the Toronto Blue Jays play. Please feel free to ask me about other areas of Toronto like dining, I know of many good restaurants there..;)

4. Posted by katezufall (Budding Member 11 posts) 12y Star this if you like it!

Hola Alex!

I am on your way. As GregW noted, there is not much between Chicago and Detroit except about 5 hours of driving. Ann Arbor (my hometown) is a great stop, just before Detroit and maybe 1-1/2 hours to the border. Ann Arbor is home to the University of Michigan (a Big Ten school), lots of trees, great people, and lots of summer activities. See re the Summer Festival (June-July) and

for our biggest events, including art fairs (in July) and a jazz festival (in September. The Michigan Theater ( is also one of only 12 venues in the U.S. hosting a series of films from the Sundance Film Festival this year.

I would echo others' notes re the car rental. Make sure you have it cleared with the rental company that you can take it through Canada AND that you are paying a minimal, if any, drop charge to return it in NYC. I would also suggest that you check on your current car and home insurance and determine what, if any, additional coverage you may need to buy from the rental company -- or to have covered by a travel insurance policy. Particularly as you will be in two countries. (so, I would look into the trip/travel insurance).

From Ann Arbor, the best route to Toronto is NOT through Detroit and the Windsor Tunnel (or across the Ambassador Bridge) but through Port Huron MI across the Blue Water Bridge to Sarnia, Ontario, Canada. This is a less used crossing so crossing is generally faster. Also this is the most direct, and shortest route to Toronto.

From Ann Arbor to Toronto is about a 5 hour drive. Be aware that once you cross into Canada and leave Sarnia behind, there will -- literally, be no where to stop for a bathroom or a snack for about an hour -- all countryside.

Besides the places others mentioned in Toronto, I would recommend The Hockey Hall of Fame (if you enjoy hockey) and seeing a play. IMHO, the top theater cities in North America are NYC, Chicago, Los Angeles, and Toronto. Like Chicago, shows are often developed in Toronto and then move to Broadway. I know that right now the big draw is the new musical version of Lord of the Rings which debuted there in March.

I would also highly recommend Montreal! Especially the Old Town -- lots of sites and activities and great food. And the bagels <-- best anywhere, baked in wood-fired ovens. Also local to Montreal are Whippets (yummy little shortbread cookies topped with a dab of raspberry jam, then covered with marshmallow and surrounded by chocolate!) and smoked meat.

Re the airline tix... GregW has it down. If you don't use part of a ticket in the middle of the routing, the whole ticket gets cancelled out. You may want to investigate getting a round trip Barcelona-Chicago and using the first part of that then a round trip NYC-Barcelona and using the first part of that OR do the round trip Barcelona-Chicago (which you may be able to do non-stop) and then buy a one-way NYC-Chicago. You'd spend more time coming back and need to allow enough international check in time in Chicago to connect, but it might be cheaper.

My husband and I are visiting Spain in October and found it cheapest to go Detroit-Chicago-Madrid RT @ about $700 each, travelling on a Tuesday. If your dates are flexible, that might also be a way to get the cost down.

Good luck and let me know if I can offer any more info.


5. Posted by judejones (First Time Poster 1 posts) 12y Star this if you like it!

Many thanks for these ideas, we, 2 adults and 3 teenagers, are travelling from Chicago to Toronto as part of a trip this August. We have organised the rest of the trip from Toronto to NY to Chicago, having spent a few days in West PA. it's the final bit we need to organise! We were hoping to spend a couple of nights en route, maybe close to a lake to chill out. Any suggestions