Travel Inspiration: Chicago

Looking for an exciting, vibrant city to visit but not feeling like the Big Apple? Chicago may be the perfect destination for you! Here’s 7 reasons why:

  • Chicago is full of amazing restaurants, entertainment, music and clubs. It is also home to more theatre than London or New York.
  • Everything is easily reachable by foot or rail with great rail connections throughout the city.
  • Millennium Park is a must see! It has a free, open air skating rink and skate rentals (if needed). The park is also home to an amazing garden, a rotation of various sculptures and the beautiful mirrored Cloud Gate and Crown Fountain.
  • During the summer months there are over 30 free outdoor musical performances offered in Millennium Park.
  • The architectural river cruises are amazing. There is great access to the river and there is even an outstanding San Antonio-like river walk lined with bars and restaurants.
  • Chicago has greeters. Greeters are locals who volunteer to show visitors around town. You can arrange a free 2-4 hour custom city tour – just try to remember to tip them!
  • Chicago is a great sports town – home of 4 major league teams. The White Sox and the 2016 World Series Champions Cubs (baseball). The Blackhawks (hockey). The Bulls (basketball).
  • For help planning your next getaway, please contact Gail at

    To read about a trip to another great city to visit please check out Boston and Cape Cod