No matter what time of year your first visit to the Windy City may occur, this vibrant metropolis in the Midwest buzzes with excitement and bursts with culture. In fact, the vast number of places to visit can feel overwhelming, so we curated a list of activities and events everyone should experience during their first visit to Chicago.
Related: Best South Loop Bars
Get A View from the Top
The famous glass floor, downward-looking view of Chicago can be found in two locations: The John Hancock Center and Willis Tower.


875 North Michigan Avenue (The John Hancock Center)
Thrill seekers head straight to the 100-floor and 1,128-foot tall John Hancock Building to get a 360-degree view from the observation deck. But, to add to the excitement of the observation deck, it offers a TILT feature, which enables downward facing views extending outward over Michigan Avenue and the general skyline from 1,000 feet up.
Willis Tower
Not to be outdone, Willis Tower’s Ledge provides a competitive option with a glass box that extends 4.3 feet out of the Tower’s 1,353-foot high Skydeck. Even if you can’t bring yourself to step onto the ledge, every first-time visitor to Chicago should ascend this icon of American history.
See the Great Outdoors
Lincoln Park Zoo
Founded in 1868, the Lincoln Park Zoo is one of the oldest zoos in America, and, better yet, admission is free. Families and friends alike can visit Pritzker Penguin Cove, observe a Great Ape Training Session, or take a stroll through the Nature Boardwalk. Planning your zoo trip over the winter months? ZooLights is a holiday-lover’s dream, complete with an astounding 2.5 million lights, ice sculpting demonstrations, a light maze, ferris wheel rides, and, of course, photos with Santa.
Ice Skating (and the Bean)
Winter lovers will also love ice skating in three special locations: McCormick Tribune Plaza, Maggie Daley Park’s ice skating ribbon, or Millennium Park, where Cloud Gate, informally known as “the Bean,” shines bright. Great for a photo op, the Bean is 110 tons of seamless, polished, reflective stainless steel.
Summer Festivals
If summer is more your forte, festivals abound in this city. Choose from an endless variety of options, starting with the Millennium Park Summer Music Series, outdoor concerts held twice a week at the Jay Pritzker Pavilion. Film festivals, music festivals, art festivals, cultural festivals, you name it, Chicago hosts it. From Ribfest to Burger fest, Pride celebrations to Puerto Rican parties, summer hops with multiple events around the city every weekend.
Related: The Inside Scoop on Living in Chicago
Enjoy the Waters
Lake Michigan and the Chicago River are unique features of this magnificent city, and water-loving visitors can choose from an array of fun and memorable options.


Navy Pier & River Cruises
Head out to the world famous Navy Pier and hop on one of Shoreline Sightseeing’s Architecture Boat Tours. Voted Trip Advisor’s most popular tour in America in 2020, the architecture tour is a 75-minute trip that goes by way too fast. Journey along the three branches of the Chicago River while hearing an entertaining history of more than 40 architectural wonders of the city. It’s truly a highlight of any visitor’s journey.
And, we can’t forget our furry travelers — the First Lady Canine Cruise offers outdoor seating, puppy water bowls, a newspaper-lined restroom, and a beautiful cruise out on the shores of Lake Michigan with our best friends.
Adventure Rentals
If adventure is more your style, Wateriders is a Chicago River Kayak Tours and Rentals company that provides private tours and sunset paddles.
LakeFront Trail and Beaches
Get an up close view of Lake Michigan by walking, jogging, or biking the 18-mile long Lakefront Trail. In the summer months, you might join the locals for a beach day, whether to swim, relax, read, play volleyball, or all of the above. Catch some rays and soak in the summer vibes at any one of Chicago’s many popular beaches.
Related: How to Spend a Summer in the Windy City
Take Some Leisure Time
Wander State Street
For visitors interested in viewing the city at a leisurely pace, shopping on Michigan Avenue’s famed Magnificent Mile can feel a bit overwhelming. Instead, head one block west to State Street in The Loop for an array of hidden gems that reflect over 100 years of history. Macy’s Spring Flower Show and holiday window displays are always a treat. In addition to big name stores, such as Anthropologie and Sephora, you can find a few local spots as well, like the Chicago Teahouse.
Museums
Hands down, Chicago’s museums are some of the best in the country.
The Art Institute of Chicago takes visitors on a complete journey through Art History, with more than 300,000 artworks. If you’re a fan of The Met, you’ll love it here.
Griffin Museum of Science and Industry is a must-see for history buffs and fans of trains, planes, and everything in between. It offers an interactive experience, complete with a restored U-505 German submarine.
The Field Museum houses some of the largest and most complete dinosaur skeletons ever found. Sue and her new friend Maximo are two of the dinos on display here.
Dive underwater at the Shedd Aquarium to encounter a variety of fresh and salt water creatures.
And finally, the Adler Planetarium is a must for all space and astronomy fans.
Don’t forget to read our list of the top 5 Chicago breweries to check out on your visit to this beer-loving city.
You’ll never run out of things to do in Chicago, but the fun doesn’t end at the city borders. Explore what lies outside the city too with these fun-filled day trips.
Come for the Attractions, Stay Forever
Once you visit Chicago, it might be tough to leave! The number of transplants grows steadily every year, and if you want to move to this exciting, yet affordable city, contact AptAmigo to help you find the perfect apartment. Most people spend 30+ hours looking for an apartment, but not AptAmigo customers. We pride ourselves in making a difficult process totally seamless. From your first phone call, we make apartment hunting a breeze. Contact us to ditch the stress of finding an apartment.
* The original version of this article was first published on April 19, 2019.


























