TL;DR: On your first trip to Chicago, prioritize skyline views, a Chicago River architecture cruise, Millennium Park, and at least one of the city’s renowned museums. Add Lincoln Park Zoo, lakefront activities, seasonal festivals, or winter ice skating based on when you visit, and check admission requirements and schedules before heading out.
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
Where Can You See the Best Skyline Views in Chicago?
Chicago offers two memorable high-rise experiences, but they work differently: 360 CHICAGO at 875 North Michigan Avenue features TILT, a moving platform that angles outward, while Skydeck Chicago at Willis Tower features the glass-floor Ledge.
875 North Michigan Avenue (The John Hancock Center)
For sweeping city views, visit 360 CHICAGO on the 94th floor of 875 North Michigan Avenue (formerly known as the John Hancock Center), approximately 1,030 feet above the city. For an extra thrill, try TILT, which slowly angles visitors outward over Michigan Avenue.
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.
What Outdoor Activities Should You Try in Chicago?
Lincoln Park Zoo
Founded in 1868, Lincoln Park Zoo ranks among the oldest zoos in the United States, and regular daytime admission is free. Explore Pritzker Penguin Cove, visit the Nature Boardwalk, or check the daily schedule for experiences such as the Ape Cognition & Care Demonstration. Visiting during the holidays? The 2026–27 ZooLights celebration features more than 3 million lights, seasonal displays, and select entertainment. Unlike regular zoo admission, ZooLights generally requires a ticket, although certain dates offer free admission with advance registration.
Ice Skating (and the Bean)
Winter visitors can skate at the McCormick Tribune Ice Rink in Millennium Park or try the skating ribbon at nearby Maggie Daley Park. While exploring Millennium Park, stop at Cloud Gate, better known as “the Bean,” for a classic Chicago photo. The striking sculpture weighs approximately 110 tons and features a polished, reflective stainless-steel surface. Check seasonal skating dates, reservations, and skate-rental details before your visit.
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
How Can You Explore Chicago’s River and Lakefront?
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
Visit Navy Pier or the Michigan Avenue riverfront for a narrated Chicago River architecture cruise. Shoreline Sightseeing offers 60- and 75-minute tours from both locations, covering all three branches of the Chicago River and more than 40 architectural landmarks. A Chicago architecture river cruise topped TripAdvisor’s most-booked U.S. tours list in 2017. It is an engaging way to learn about the buildings that shaped the city.
Traveling with your dog? The seasonal First Lady Canine Cruise runs on select weekends from July through October. Guests and leashed dogs can enjoy an open-air deck, onboard water bowls, and views of the Chicago skyline. Check its schedule and pet guidelines before booking.
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
Explore the shores of Lake Michigan using Chicago’s dedicated Lakefront Trails, which include an approximately 18-mile route for cyclists and a separate 18.5-mile route for pedestrians. Watch for seasonal maintenance and any posted detours. In warmer weather, enjoy the city’s public beaches for relaxation, reading, or volleyball. Swimming is allowed only at designated beaches while lifeguards are on duty during beach season.
Related: How to Spend a Summer in the Windy City
Take Some Leisure Time
Wander State Street
For a more leisurely shopping day, consider Chicago’s historic State Street in the Loop, west of Michigan Avenue’s famous Magnificent Mile. You can browse major retailers, including Macy’s State Street and Sephora. Macy’s hosted a seasonal Flower Show pop-up here from April 16 through May 10, 2026; check its events calendar for future seasonal displays. If you want to continue north along State Street into the Gold Coast, visit Chicago Teahouse at 1160 N. State Street.
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 saltwater creatures.
And finally, the Adler Planetarium is a must for all space and astronomy fans.
Don’t forget to read our list of the best breweries in Chicago 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
Enjoyed your first visit to Chicago and thinking about moving here? AptAmigo helps renters explore apartment options that match their preferred neighborhoods, budgets, and priorities. Our Chicago apartment locators help with recommendations, scheduling, and tour logistics so you can spend less time coordinating your search. Contact us to get started.
Apartment Spotlight: Neveseno
* The original version of this article was first published on April 19, 2019.
FAQs
This article was AI-generated by AptAmigo.
