Things to do During Your First Trip to Chicago

by AptAmigo | Apr 19, 2019 | Chicago, Exploring Chicago

No matter what time of year your first visit to the Windy City may occur, there truly is something for everyone within this vibrant metropolitan in the Midwest. Here is our curated list of things everyone should see 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.

The John Hancock Center

The 100-floor and 1,128-foot Hancock Building is where thrillseekers can get a 360-degree view from the observation deck. But to add to the excitement of the observation deck, it has a TILT feature, which offers 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 offers a competitors’ option in terms of a glass box that extends 4.3 feet out of the Tower’s 1,353-feet high skydeck. For those wanting a view but with less heart pumping action, head down to the Hancock Building’s 96th and 95th floors to the Signature Room or Lounge. While the elevator ride is free, a drink and a casual moment are worth the views. Fun fact: the view from the men’s and women’s bathrooms are amazing.

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-lovers’ 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 offerings in three locations: McCormick Tribune Plaza, Maggie Daley Park’s ice skating ribbon or Millennium Park, where Cloud Gate — informally known as “the Bean” is housed. 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 the 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. The 4th annual Chicago House Music Conference and Festival, 34th Chicago Gospel Music Festival, 36th annual Chicago Blues Festival, Grant Park Music Festival, 41st annual Chicago Jazz Festival and the 21st annual World Music Festival Chicago are also coming to the city in the summer of 2019.

Enjoy the Waters

Lake Michigan and the Chicago River are unique features of this magnificent city, and water-loving visitors have fun options that are sure to be remembered.

Navy Pier & River Cruises

Head out to world famous Navy Pier (which is undergoing some much-anticipated renovations) and hop on one of Shoreline Sightseeing’s Architecture Boat Tours. Voted Trip Advisor’s most popular tour in America in 2017, the architecture tour is a 75-minute trip that goes by way too fast. Journey along the three branches of the Chicago River while getting a 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 Mercury 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.

Take Some Leisure Time

Wander State Street

For visitors looking to view the city at a leisurely pace, shopping on Michigan Avenue’s famed Magnificent Mile can be a bit overwhelming. Instead, head one block West to State Street in The Loop for an array of hidden gems that reflect a 100 plus year history. Macy’s Spring Flower Show and holiday window displays are always a treat. An the family-owned Merz Apothecary is an “old-school” shopper’s dream, located in the Palmer House Hilton Hotel.


If art is on your list, Chicago’s museums are some of the best in the country.

The Art Institute of Chicago is 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.

The 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 is home to 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.

And finally, the Adler Planetarium is a must for all the space and astronomy fans.

Don’t forget to read our list of top 5 Chicago breweries to check out on your visit!

Once you visit Chicago, it might be tough to leave! The amount of transplants is growing steadily, and if you’re looking to make a 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 very first phone call, we make apartment hunting a breeze. Learn More here, and contact us to ditch the stress of finding an apartment.

About Us

AptAmigo has a simple goal: to make finding an apartment easy and maybe even a little fun. With concierge-level care and an expert understanding of the local rental market, we’re more than your average apartment website. We’re perfecting done-for-you apartment searching, and we’re doing it all for free. Reach out to us today and start your VIP apartment search.

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