Answers from Our Experts (3)
You’ve likely heard about the big-time attractions in Chicago: Navy Pier, Millennium Park, the Magnificent Mile. While these spots are perennial favorites with visitors and are worth at least a quick look, you may also want to make like the locals while you’re here.
First up? Grab brunch — preferably at a spot with an outdoor patio like The Publican or Perennial Virant. Brunching is practically a rite of passage on the weekends here. During the warmer months, go for a walk, run or bike ride on the path along Lake Michigan or hit North Avenue Beach. In the cooler months, hit up a museum (the Art Institute of Chicago and the Museum of Contemporary Art are excellent choices) or an art gallery (Kavi Gupta in the West Loop is a favorite).
For an upclose view of the city you won’t find atop the Willis Tower or from the Ferris wheel on Navy Pier, head to one of River North’s luxury hotels for a cocktail — Trump International Hotel & Tower, The Ritz-Carlton Chicago and Park Hyatt Chicago all have outdoor decks high above the city streets.
To get your bearings and take in one of the best views of the entire city, I recommend cocktail hour at the Signature Lounge on the 96th floor of John Hancock Center. It's pricey but worth it, and oddly, one of the absolute best views is from the women's lounge. Sorry, gents!
Weather permitting, you're going to want to get on the water at some point. My all-time favorite activity for both first-time visitors and long-time residents is to get tickets for the Chicago Architecture Foundation's architectural boat tour, which winds down the Chicago River's main branch with a well-versed docent at the helm. Especially in fair weather, this is one of the most awesome ways to take in downtown Chicago and its incredible architecture.
Chicago loves (like, really loves) its sports teams, so if you can score tickets to a game while you're visiting, you're guaranteed to have a good time. During baseball season, Sox tickets are generally more obtainable than Cubs, but both stadiums are easily accessible via the CTA, Chicago's efficient public transportation system. (Just don't ask a local to choose between the rival teams, and you'll be fine.) For winter sports, forego a freezing four-hour Bears game (brr!) and instead look into getting tickets to the Blackhawks, who not too long ago brought home the Stanley Cup.
If it's summer in the city, you have to find a way to get on a boat. Chicago's skyline is especially majestic when viewed from out on Lake Michigan. Luckily, there are a few easy ways to get out on the water. Navy Pier offers a number of boating options, from dinner cruises to speed boat tours. (FYI: That's also where you'll view an impressive fireworks show on Wednesday and Saturday nights.) The Chicago Architecture Foundation boat tours take you through Chicago's river, where you'll get new views (and some background info) on some of the city's most famous buildings.
Bike riding is becoming more popular in Chicago. Proof: Divvy Bikes recently set-up a bike-sharing program throughout the city, where you can rent a bike for the day and pick it up at any docking station. Riding a bike along the lakefront path is also a great way to see Chicago like a local.
Chicago also has a great theater community, and if you have time to see a show, I'd definitely recommend it. There's always Second City, The Goodman and Steppenwolf as well as the many storefront theaters located throughout the city. Many famous actors (including Tina Fey, John Malkovich, John C. Reilly and more) got their starts on Chicago stages, so chances are you'll catch a performance from the next big thing.