Skip to main content
  1. Travel
  2. Local Getaways

Shop, Eat and Play in Chicago

See also

Shopping in Chicago

Rating:
Star5
Star
Star
Star
Star

If you're planning a relaxing, kick back vacation, Chicago is not your spot. But, if you are looking for a non-stop, culture filled shopping mecca, say hello to the gem of the Midwest! For shopping, stroll down State Street to visit Macy's in the historic Marshall Field's building, run up and down the Mag Mile and hit the trendy boutiques of Oak Street, where you can easily do your part to help boost the nation's economy. In addition to great shopping venues, the city also offers world-renowned dining, museums, architecture, theater, music and more.

State Street, That Great Street!
Begin your shopping adventure on State Street, home to Chicago's landmark department stores, Macy’s, H&M, Nordstrom Rack, Sephora, the Disney Store and much more. A walking tour of the old Marshall Field’s, now Macy’s, will prove that its’ rich history matches its significant architecture. This tour traces the construction, development, and renovation of this State Street landmark. You’ll be able to explore the 800,000 square feet that has made this structure infamous and have a customized appointment with one of Macy’s Personal Shoppers. Lunch at the elegant Walnut Room and a box of Frangos, Marshall Field’s signature chocolates, will complete this shopping excursion.

Dinner and Second City
After a long day of shopping, I always enjoy dinner in the Old Town area of the city. Topo Gigio, a favorite among locals, visitors, and celebrities, and classed among the top 5 Italian restaurants in Chicago, is definitely a favorite of mine. If Italian is not your thing, there are many other options for restaurants all within walking distance. Looking for a good laugh? Top off your evening with a show at the famed Second City Improv Theatre, a Chicago landmark that has launched the careers of such comic greats as John Belushi, Mike Myers, Bill Murray, Gilda Radner, and more.

Mag Mile
Your shopping fantasy continues on the Magnificent Mile, one of the world's glitziest shopping boulevards. You'll want to visit the multi-storied shopping malls like Water Tower Place, 900 North Michigan and the Shops at North Bridge. But don't neglect the trendy boutiques on fashionable Oak Street, Nike Chicago or that Valhalla for little girls, American Girl Place.

Eat Chicago Style
What makes eating out in Chicago fun is the variety. They've got it all: For lunch, sample Chicago pizza at local pizzerias like Uno’s or Giordano’s or for a more adventurous palate your can enjoy stylish see-and-be-seen spots, an amazing array of steakhouses, chef-owned temples to fine dining, and every kind of ethnic cuisine you could possibly crave. Because there are too many to list, here’s a restaurant guide in order to navigate these amazing restaurants.

High Tea at the Drake
Take a break from all the heavy lifting (of your credit card, that is) and enjoy a late afternoon of High Tea at the famed Drake Hotel. The Drake Hotel is a Chicago landmark and has been a symbol of white glove elegance for over 80 years. This is how you were meant to live!

Off to the Theatre
If you’re a fan of Broadway, check out Chicago’s theatre district. Here you can sample world-class theater at the Goodman Theatre or Steppenwolf Theatre; enjoy a Broadway-style show at the Cadillac Palace Theatre, the Ford Center for the Performing Arts/Oriental Theatre or many other theatres around the city.

Whatever you're looking for, you'll find it in Chicago. It's your kind of town!

Advertisement