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Which city to visit: Boston or Chicago?

edited March 2010 in - USA
I'm on a trip to the States and I've got a choice of a weekend break in Chicago or a weekend in Boston? What do I choose? I like live music, great art and some outdoor activities... Any call on which of these two awesome cities I should go for?

Thanks for any advice, Simon A


  • edited 8:34AM
    Both cities are great! However, if you only have a weekend, I would select Boston. Boston is compact and easy to get around. It has good public transportation, and taxi service. The different areas are small enough to walk it, too. You will love the museums. Harvard, in the Cambridge area, has a great Natural History Museum. The campus itself is awesome to walk around. Harvard Square is full of activity. The Museum of Fine Arts, is excellent. Also, you can walk the Historical Freedom Trail. The entire city has a trail line to follow and relive the history of the city. Paul Revere's home, the Old City Market, Faneuil Hall, The Revolutionary War monument of Bunker Hill, and Beacon Hill with the charming cobblestone streets such as Acron St, are among the delights on this trail. is a good site for looking at all the things to do and see during the time you are visiting. is a great company to use if you like more explanation during your walks. They do a great job. Don't miss the Harbor front and the city Aquarium. The Boston Harbor Hotel is on Rowes Wharf, across the street from the Financial District and 2 blocks from Faneuil Hall Marketplace. It is the best place to stay if you want the water views and the beat of the city. The 2nd area I would stay around would be Copley Square. The best dining is around Tremont Street or eat in the oldest Tavern in the USA, The Union Oyster House...where our forefathers met to discuss the politics of the day. B&G Oyster House is another favorite of mine. Ask to sit at the kitchen bar to watch the chefs do their thing! If you enjoy Italian, you must go to the North End. There are excellent Italian restaurants everywhere. Hope you enjoy your weekend! Crissy
  • edited 8:34AM
    Crissy, thanks so much for the advice. I hope you don't mind a few more questions. First up: is it possible to do a 1 day ski trip from New York City in early April? Are there are any resorts close enough to make this viable?

    Second option: How long would it take to get to Boston from NYC and what's the best way? Train is my preferred mode - is this a good idea and cost effective?
    Thank you, Simon
  • edited 8:34AM
    Go to Chicago one of the worlds greatest cities.
  • edited 8:34AM
    I love to ski, too, however, with only 1 day, you'd spend the entire day traveling. Best to wait for a 4 day weekend. 2hrs from NYC is Hunter Mt, in the Catskills, but it is only 1600ft vertical. Killington & Stowe Vermont are the other mts, but they are 5-6 hrs from NYC. It is best to fly to the Rockies, Direct flights to Denver with evening flts. You could leave on a Thurs or Fri eve. and be in a resort by midnight. Winter Park and Loveland Ski area are closest to Denver. Direct flts also to Salt Lake City. Slopes are close to the airport. Buses run from the airport. Alta is a super mt. Crissy
  • edited 8:34AM
    Crissy, have you ever gone skiing at Mountain Creek in NJ? Do you know any transfer services that take people from New York to the mountain and back for day trips?
  • With its glittering lights and joyous atmosphere, Chicago is a delightful, snow-filled wonderland.mosphere, Chicago is a delightful, snow-filled wonderland.
  • Both are great city. But its totally depend on you were you want to visit.
  • Both are good city.but according to me if i choose than i choose Chicago.
  • Personally, I love Chicago:-)
  • I worked in Chicago and while I enjoyed my time I prefer Boston , more from a historical point of view.
  • Yeah both places are really beautiful and very impressive and fascinating and attract the tourist from all over the world to watch it.I,m a tourist and explore many countries yet.I am a history lover also so i prefer Boston then Chicago.I take a lot of information from this city and some of my friends also lived there so i preferring it according to my point of view.
  • edited July 2015
    I have been to Boston and its an awesome place.I would suggest you to refer "Boston in 20 Minutes" by Cristiano Nogueira. Its one of the best travel guides with a good selection of attractions, points of interest and excellent places to dine .
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