Ah, the Windy City. But there is other stuff besides wind in Chicago, right? Luckily, the answer is yes. And if you are only planning on spending a weekend in Chicago, we have outlined nine activities that will maximize your time while also giving you a true taste of the Chicago experience. Plus, do not forget to book a comfortable, upscale Chicago vacation rental, so you can enjoy everything this city offers even on your down time.
See the view from the Willis Skydeck
Start your weekend in Chicago with a trip to the Willis Skydeck, a classic Chicago activity where the bird’s eye view of the city extends over 50 miles. And if you are feeling brave, you can even step out onto The Ledge, a glass box jutting out from the side of the Skydeck, over 1,300 feet above the city.
Take a classic photo in Millennium Park
After your morning at Skydeck, head over to Millennium Park where the iconic Cloud Gate (aka, “The Bean”) is located. Gaze upon this enormous sculpture inspired by liquid mercury that reflects the Chicago skyline off of its stainless steel, and of course, take a picture to prove you were truly in Chicago.
Eat deep dish pizza
Obviously if you go to Chicago and do not eat deep dish pizza did you even, like, go to Chicago? Chicago is basically the deep dish pizza capital of the world and luckily there are plenty of opportunities to try out this national treasure. Our top picks? The caramelized crust at Pequod’s or the strange, but wonderful “pot pie” pizzas from Chicago Pizza and Oven Grinder Co.
Catch a show at Second City
Finish up your first night at Second City, the infamous improv theater where the likes of Amy Poehler, Steve Carell, and Stephen Colbert performed in their early days. If you are a comedy history buff, the Best of Second City Show is 90 minutes of the best sketches from all of Second City’s 58 years, so you are guaranteed to watch something your favorite stars once performed.
Spend the morning on the the Lakefront Trail
If your weekend in Chicago takes place during warmer months, a few morning hours on the Lakefront Trail is a relaxing way to break up your time in the city. Located along the shore of Lake Michigan, the Lakefront Trail is an 18-mile path perfect for biking, jogging, or just a simple stroll as you take in Chicago’s skyline from a new perspective.
Visit the Shedd Aquarium
Even a few hours at the Shedd Aquarium is worth it to see the over 32,000 animals that live, swim, and play there. And if you are looking for a Chicago activity for families, the Shedd Aquarium offers up close encounters with seals, otters, and even beluga whales.
Grab lunch at Hot “G” Dog
Hot “G” Dog, which replaced Chicago institution Hot Doug’s in 2015, is one of those places to go if you truly want to experience the type of cuisine all the locals know about and love. Hot “G” Dog serves classic Chicago hot dogs, yes, but they also serve quirky and delicious creations like the jalapeno bacon sausage hot dog with roasted grape sauce, roasted almonds, and cranberries. Um, yes please.
See a show at The Yard
The Yard Theatre is a new addition to the Chicago arts scene, but has already become a cannot-miss Chicago activity. Completed in 2017, The Yards is a innovative theater space that is completely flexible, consisting of nine towers of audience seating that can be moved into any position to accentuate the particular feel of a production. You can truly say you have had a one-of-kind Chicago experience after a show at The Yard.
Go to the Green Mill Cocktail Lounge
For your last night of you weekend in Chicago, we recommend hitting up the Green Mill Cocktail Lounge, a jazz club with an infamously rich and sordid history. First frequented by the likes of Frank Sinatra and Charlie Chaplin, the lounge was eventually overtaken by the Chicago mobsters of the 20’s and 30’s, including Al Capone himself. Today, the Green Mill Cocktail Lounge is a must-visit spot in Chicago with live music every night of the week until four in the morning.
With these nine activities, you are sure to leave Chicago feeling like you had a full experience, even if it was only the weekend!