The Windy City. Whether you know this city in all its glory from the film Ferris Bueller’s Day Off or your own personal despair during yet another unexciting business trip, Chicago has certainly earned a reputation. In reality, it’s actually a city with a rich history and a whole lot of character. Hopefully, this guide will shed some light on a few gems and tourist staples for the next time you’re looking for an urban getaway.
Chicago is a very walkable city. Many places of interest are close enough together that you’ll end up traversing half the city on foot without even realizing it. Cities are like that; they’re intuitive. With something new and exciting around every corner, you’re sure to get your steps in. That being said, there’s something special about exercising in nature, and Chicago has no shortage of parks to explore.
The quintessential Grant Park boasts lakefront views and cultural standouts that make it a must-visit. On the north end sits Millennium Park, home to Cloud Gate, or “The Bean” as it’s more commonly known. Snap some photos early in the morning during weekdays on your way to breakfast and cherish the sparse crowds. There are also gardens, public art displays and an amphitheater, making this a gathering hub of the downtown. The gorgeous centerpiece of Grant Park is Buckingham Fountain. Its waters flow May through October with a water and light show every hour.
A quick train ride to the Lincoln Park neighborhood of the city allows visitors access to the Lincoln Park Zoo, one of the last free zoos in the country. Exhibits include the Helen Brach Primate House, Farm-in-the-Zoo, McCormick Bird House, Walter Family Arctic Tundra, Penguin Cove and more. Both children and adults alike can spend hours wandering through all the different exhibits with all kinds of animals to see. When you’re done, venture further into the park for a beautiful, lakeside stroll.
If you prefer a bit more structure for your movement, try out a yoga class at the Lighthouse Art Space. Enjoy about 30 minutes of yoga before being released into the space to experience the artistry of Van Gogh or Frida Kahlo. This unique wellness offering allows you to become fully engrossed in these two artists’ works. Instructors may invoke a mantra reflective of the artist, deepening your connection to the space and reverence for these amazing painters.
For an atmospheric and tasty brunch, check out The Hampton Social. Whether you’re there for the drinks, apps or a full meal, not a single thing on the menu disappoints. Bring your friends and prepare to settle in for a meal full of coastal vibes and great eats. I highly recommend the frosé and crab bruschetta appetizer. Plus, their River North location showcases the iconic “Rosé All Day” wall to display proudly in your Instagram feed.
An excellent lunch option is Goddess and The Baker. With long tables inside that evoke a communal dining feeling and cute café-style seating outside, this is certainly a place to sit and stay a while. Order a specialty coffee concoction, choose a main from their breakfast or lunch menu (both are served all day) and indulge in one of their many baked goods, enticingly displayed right by the door.
Okay, now the recommendation you’ve all been waiting for. Chicago is known for their pizza, specifically the Chicago Style or deep-dish pizza. While I could give you a long (really, really long) list of pizza places to check out, I think I should leave it to the expert. If you’re as much of a pizza fanatic as I am, I definitely think it’s worth it to embark on the Chicago Pizza Tour. Jon Porter, the founder of the tour, was my guide, and I can confidently say that there is no better leader of a “pizza support group,” as he calls it. Deep dish or thin crust. Cheese, tomato sauce, crust consistency, toppings. Jon imparts a plethora of knowledge about the various pizza-making processes and the history behind each pizza place on the tour. Lou Malnati’s, Pizano’s, Unos, Coalfire. The line-up changes depending on the tour, but trust Jon, and you’ll end the tour more stuffed than a pizza crust full of cheese.
Finally, the cherry on top — dessert. Jeni’s Splendid Ice Cream is an absolute must for any ice cream enthusiast. The glorious smell of waffle cones greets visitors upon arrival. Then, stare at the menu and ponder what the best flavor combination will be. My personal favorite is the coffee ice cream paired with vanilla. Simple, but a match made in heaven. All of their ice creams are extremely smooth and flavorful, and they offer a few different vegan-friendly options. I went to Jeni’s twice during my visit; it was that good. And, they sell pints to take home, so customers can down a whole pint from the comfort of their own couch. Pure bliss.
There is so much to do in Chicago and truly something for everyone. For the all artists out there, The Art Institute of Chicago is insanely impressive. I visited from open until close (with a break for lunch) and still didn’t manage to see everything. With four stories filled to the brim with incredible works of art, including some from renowned artists like Georgia O’Keefe, Monet and Pablo Picasso, there is no shortage of breathtaking artwork to experience. And for modern exhibitions, check out the Museum of Contemporary Art which showcase timely, insightful pieces from today’s rising artists.
Interested in a good laugh? Stop at the Museum of Illusions to witness mind-bending illusions and puzzles. With a goal of educating and entertaining, the Museum of Illusions is a great place for the whole family to learn more about the brain’s inner workings while having a blast with their 80-plus exhibits. For exclusively adult groups, a comedy show put on by Second City will definitely end in some rolling-on-the-floor laughter. Second City is the birthplace of a ridiculous number of comedians that have become household names — Bill Murray, John Candy, Tina Fey, Amy Poehler, Dan Aykroyd, John Belushi, Catharine O’Hara, Mike Meyers, Gilda Radner, Steve Carrell … the list goes on and on. Many of their shows are improvised and ask for audience participation. Becoming part of the show makes it that much more entertaining, engrossing and exciting. Who knows when you’ll become the butt of the next joke!
Finally, for visitors who love a good tour of this historic city, two stand out above the rest. First, the Chicago Crime Tour, which dives deep into the, at times, seedy underbelly of the city. But as you’ll learn on the tour, so much of the city wouldn’t be the way it is today with these notorious crime bosses. While the tour is offered at various times throughout the day, I recommend going on one of the night tours to heighten the spook factor of the experience. My other recommendation is the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady. Yes, it’s a mouthful, but the CAFC River Cruise is packed full of fascinating information about the city’s one-of-a-kind architecture. The Chicago fire altered the trajectory of construction leading to a unique amalgamation of different architectural styles. Since you’ll be outside and on the river for the tour, I suggest going on a warmer day. I did not check the weather prior to my tour, which was a mistake to say the least.
In this bustling city, there’s no shortage of lodging options, from unique bed and breakfasts to apartments allowing renters to get a taste of local life. But there’s certainly something special about a hotel stay, especially a high-end experience like that offered by Swissôtel Chicago’s Vitality Suite. The Swissôtel is located just steps from the Chicago Riverwalk and the Magnificent Mile and is just a short walk away from Millennium Park. The suite itself provides incomparable views of Lake Michigan and includes five rooms, two bathrooms and a wellness area equipped with a Peloton bike, water rowing machine and wellness wall with additional exercise equipment. The all-glass hotel also offers a Penthouse Fitness Center on the 43rd floor to ensure all your wellness needs are met.
Seeking to combine design elements both old and new, Viceroy Chicago is another great luxury option for accommodations. Located on State Street, Viceroy also provides easy access to the Magnificent Mile for shopping, as well as a straight shot to the lakefront. The outside of the building is a little deceiving; a squat brick building gives way to a towering glass structure above. While a bit tricky to decipher from the ground floor, this combination of styles emulates the old transitioning into and blending with the new. Visitors are sure to feel the historic neighborhood coziness, with all the benefits of modern upgrades.
Learn more at choosechicago.com.
All photos by Lauren Farrauto, unless otherwise noted.