To commemorate living in the Midwest for a decade, I decided to pen my definitive list of tried and true Chicago experiences. This isn’t a list of the newest or hippest (or hipster-est) hangouts, but rather the places that have kept me coming back again and again. There’s something to be said for staying power!

The one classic Chicago experience I heartily endorse is taking an architectural boat cruise down the Chicago River. This is so popular that it’s quite easy to show up at N Michigan Ave & E Upper Wacker Dr and buy a ticket on the spot. To enjoy the Chicago River at your own pace, rent a kayak or pontoon boat instead. If you choose to enjoy the Chicago Riverwalk by foot, stop by the Centennial Fountain to see the water arc shoot off. Finally, there’s always the option of taking what I call “the poor man’s architectural cruise” by boarding the Chicago Water Taxi or better yet, the Shoreline Sightseeing Water Taxi. Its two taxi routes run between Union Station/Willis (Sears) Tower and Navy Pier, as well as between Navy Pier and Shedd Aquarium/Museum Campus. I highly recommend catching the sunset — and a beautiful panorama of the city — from the grassy hill overlooking Monroe Harbor at Museum Campus.

The other classic experience I recommend is taking a picture of yourself (and a dozen other tourists) in front of Cloud Gate (The Bean) at Millennium Park. While you’re there, cross the street to view the free art exhibits at Chicago Cultural Center, my favorite architectural gem in the city. Be sure to swing through Preston Bradley Hall and admire the ceiling.


Chicagoans live for summer. We overindulge in street festivals and block parties as a reward to enduring the icy wind chill and subzero temperatures from December to March. Here’s how I chase away the winter blues:

While Ferris Bueller is probably Chicago’s most loved movie, many movies have been filmed in Chicago. I always get excited when I recognize Chicago film locations.

Believe it or not, it is possible to survive winter in Chicago! Even fall is fun. My absolute favorite Chicago even happens each October: Open House Chicago. Here are more recommendations, many year-round:

Plus, Chicago has plenty of events of a more cerebral nature:

The event listings are endless on Thrillist, Sosh, Timeout and Do312. I’m constantly snagging deals on Gilt City, Goldstar, Hottix, Travelzoo, Groupon and LivingSocial.

Chicago has great drop-in classes!

  • Second City: choose between improv acting, writing and musical improv. It’s the best kept secret in Chicago!
  • Old Town School of Folk Music: in addition concerts, the school offers a variety of music and dance classes! (Note: it is not actually located in Old Town)
  • Trapeze School New York: fly high over Belmont Harbor in summer and at the Broadway Armory during the rest of the year
  • Chopping Block: improve your cooking skills and then enjoy your creations
  • Flirty Girl Fitness: giggle and get strong at the same time

And there are plenty of streets for strolling and shopping:

  • Loop: along State Street or the Magnificent Mile
  • West Loop: love shopping at M2057 by Maria Pinto
  • Old Town: along Wells from Division to Lincoln
  • Bucktown: head north or south on Damen from the Blue Line stop
  • Lincoln Park: start at Halsted & Armitage; go west on Armitage or north on Halsted; oh, and try the peanut butter bon-bons at Vosges Chocolate Haus
  • Andersonville: stroll along Clark, stopping for ice cream at George’s Ice Cream and Sweets or a beer at Hopleaf Bar

My favorite designer boutiques include:

Here are my favorite lesser known Chicago gems:

Here are my favorite hotel lobbies:

  • Check out the peacock doors on your way into the ornate lobby at Palmer House on State Street
  • Blue Bottle Coffee and salty dark chocolate cookies served at Soho House
  • I come for the cloud-like chocolate cookies that accompany espresso at Salone Nico at Thompson Chicago

Sampling Chicago’s native foods is a given — specifically Giordano’s deep dish pizza, Portillo’s Chicago hot dogs, Borinquen’s jibaritos and Garrett’s popcorn (the Chicago mix is butter, cheese and caramel – all in one bag!). I can only handle so much of those dishes; but these local specialties keep me coming back over and over again:


Lunch & Cheap Eats

  • Xoco by Rick Bayless: milanesa torta (sandwich) with extra salsa on the side
  • Big Star: taco al pastor and chips with guacamole; you’ll have enough chips to warrant an extra guacamole to go!
  • Penny’s Noodle Shop: hot pepper noodles with beef
  • Irazú: chifrijo paired with an oatmeal shake made with soy milk
  • Tank Noodle: pho or bun thit nuong cha gio
  • Lula Cafe: menu changes seasonally and I’ve always enjoyed it all
  • Many options at Chicago French Market; I always stop at Saigon Sisters for the Hen House sandwich
  • 3 Arts Club Cafe at Restoration Hardware: not quite in the “cheap” category, but the ambiance in the skylit dining room is worth the visit




While Chicago may not have the same depth of weekend getaways of place like San Francisco or D.C., there are a few places worth visiting outside of the Windy City:

  • Illinois: Hike Starved Rock and check out the Illinois Wine Trial on the way; or head down near Missouri to see historic Cahokia Mounds, toward Iowa to visit Galena or toward Wisconsin to visit Lake Geneva
  • Wisconsin: city strolling in Milwaukee or Madison; hiking or skiing Devil’s Head State Park
  • Indiana: Indiana Dunes or relaxing at a lake house
  • Michigan: Hike Warren Dunes and have your fill of Michigan blueberries, cherries, apples and pumpkins from the numerous farms you’ll pass along the way; plus there are cider mills and breweries galore, including Virtue Cider, Founder’s, Grand Rapids Brewing Company and Brewery Vivant. There are still many Michigan wineries I want to try!

Even after ten years here, there’s still more I want to do! Chicago, you’re A-OK by me…

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