TL;DR: Chicago has plenty to do for families, career-driven individuals, couples, and seniors alike. From free attractions like parks and museums to high-end luxury, boredom is never an option.
Are you considering a move to Chicago, Illinois in 2026? Or maybe you’ve already decided to relocate for professional reasons. Either way, researching the top attractions in Windy City should form a key part of your preparations.
While finding the best Chicago rentals gives you the foundation for building a better life, appreciating the city’s vibrant atmosphere and most popular attractions will enrich your life and help you feel like a Chicagoan in no time.
Whether moving to Windy City for a few months or relocating for life, this guide on what to do in Chicago will provide ample inspiration.
The Diversity Of Chicago Attractions
As the third largest city in America, Chicago unsurprisingly has a lot to offer its 2.7 million residents and millions of annual visitors.
Even before you search rental listings in Chicago, the following points should help you appreciate Windy City as a great place to live a fulfilling lifestyle;
- Chicago is served by an excellent public transport network. Even renters who do not own a car will find it very easy to explore Chicago in style.
- The city boasts world-class attractions and experiences across dining, entertainment, sports, music, nature, and so much more.
- Chicago additionally has plenty to offer at all price points from free concerts and trails to luxury high-end experiences.
- Windy City also has everything from highlight attractions loved by tourists to daily life experiences that are arguably more geared towards residents.
- There are plenty of things to do in Chicago regardless of whether you seek family-friendly attractions, data nights, or solo activities.
Furthermore, Chicago’s attractions are spread out across the city center and across all neighborhoods into the suburbs. So, what are the best things to do in Chicago for renters in 2026 and beyond? Here’s all you need to know:
Chicago Riverwalk
The Chicago Riverwalk is one of the city’s most iconic attractions, but it is equally impressive for locals as visitors. The 1.25-mile stretch covers four distinct areas (The Confluence, The Arcade, The Civic, and the Esplanade) to provide proximity to the Chicago River. The attraction is free to all, although paid activities are available.
Whether enjoying the waterways or planning to get out on the water, it is the perfect setting for things to do throughout the year. Unsurprisingly, there are plenty of brilliant places to eat and drink nearby at various stages of the Riverwalk. It is also an idyllic way to find routes into the best nearby attractions.
Art Institute Of Chicago
The world famous Michigan Ave is home to several attractions including the Magnificent Mile, but the Art Institute of Chicago is one that no new resident of the city should sleep on. Aside from the breathtaking nature of the artworks, it is a venue that instantly makes you feel more connected to the city.
After all, many of the pieces and exhibitions are from local artists, often depicting life in the incredible city. Soaking it all in while surrounded by locals is an experience you should look to enjoy within the first few weeks of living in Windy City. And not least because you then step back out onto the iconic avenue.
Chicago Water Tower
Built in 1869 and found on Michigan Avenue, Chicago Water Tower is a building of huge historical significance for the city. It famously survived the Great Chicago Fire of 1871, cementing its status as a symbol of resilience for locals throughout Windy City. Visiting it is a moving experience.
Simply seeing the iconic water tower makes you feel closer to the city’s history. However, there are plenty of guided tours, as well as city bus tours, that include this attraction on its itinerary. While it could be argued that this is a touristy way to explore your new home city, you will learn a lot from it.
Field Museum
As a major city, Chicago is home to several museums but The Field Museum of Natural History is arguably the best. Situated at 1400 S Lake Shore Dr, it is best known for SUE the T-Rex. It is an epic sight that you won’t forget in a hurry while the Evolving Planet section also contains the life-sized Quetzalcoatlus.
However, Field Museum additionally hosts a number of exciting exhibits and artifacts to explore. Notably, the Pokemon exhibition is ideal for families with young Pokemon fans. Or big kids who have been collecting Pokeballs since the 90s. There’s free entry while even the paid exhibits and tours offer good value for money.
Lincoln Park Zoo
Lincoln Park Zoo is a 35-acre attraction that sits in the heart of Chicago’s Lincoln Park. It’s free to enter, providing over 3.4 million annual visitors a chance to see over 200 species of animals. Alternatively, you can pay to get up close and personal with select animals courtesy of zookeeper experiences.
Whether seeking a wallet-friendly day out or a local attraction that offers a once-in-a-lifetime experience doesn’t matter. Lincoln Park Zoo is one of the best. As the second oldest zoo in the country, it is ingrained into the very fabric of Chicago. The Helen Brach Primate House exhibit is a particular highlight.
Lake Michigan
Lake Michigan is one of the five Great Lakes and the third-largest by surface area (second by volume) of them all. Amazing views are enjoyed from virtually every spot along the lake, where you can find a total of 33 beaches without leaving Chicago. Of course, an array of water sports are available to be enjoyed.
An 18-mile paved path, known as the lakefront trail, is another highlight. Many locals use it for walking, jogging, and cycling on a daily basis. It’s a chance to exercise while embracing the epic views and feeling the fresh air on their lungs. However, an afternoon lazing around on one of teh beaches is just as enjoyable.
Millennium Park
Millennium Park was opened in 2004 as a 24.5 acre public park on the Lake Michigan shoreline. Visited by thousands of people daily, including locals and tourists alike, it is one of Chicago’s best attractions. Not least because it provides the perfect counterbalance to the hectic nature of the city center.
The park is home to the iconic Cloud Gate statue, also known as the Bean. Interactive fountains, public art, skating rinks, and trails are also available. You can additionally find a host of free events and green space. Paid tours and activities are also readily available, offering exceptional versatility for days out on your terms.
Shedd Aquarium
Opened in 1930, Shedd Aquarium is a huge public attraction that’s home to over 32,000 animals including Beluga Whales and incredible species from North America and beyond. Residents get free access to the entire aquarium, including its exhibits, at certain times too. So, it is truly one of the best attractions offering good value to renters throughout the city.
The huge tanks transport you to a whole new dimension while the layout of the venue provides a comfortable and convenient experience. Guided tours lasting 75 minutes are available or you can explore at your own pace. Either way, it is truly a fantastic day out for families, couples, or solo renters alike.
Wrigley Field
Historic Wrigley Field is home to the city’s three-time MLB World Series winners the Chicago Cubs. Whether you catch a game at the iconic venue or book a tour, the electric feel is palpable. Located in the North Side district of the city, the stadium first opened its doors in 1914 and has brought Chicagoans together ever since.
Away from Wrigley Field, you could visit Rate Field, which is home to the city’s other MLB team the Chicago White Sox. The city’s other sports teams include the Bears (NFL), Blackhawks (NHL), Bulls (NBA), Sky (WNBA), and Fire (MLS). The atmosphere of gameday at any of them is sure to fill you with local pride in your new home city.
The United Center
The United Center is located in the Near West Side Chicago and stands out as the city’s biggest indoor arena. Its resident sports teams are the Bulls and the Blackhawks. So, it is the venue to catch a home game of your favorite basketball or ice hockey team. However, the venue is also used for so much more.
There is always something happening at the venue, which can hold 23.500 spectators for concerts. Having opened in 1994, it has witnessed some epic nights as well as huge sporting moments, not least for the late 20th-century Bulls teams. From events to tours, it is a must-visit venue for anyone living in the city.
Soldier Field
If the unmistakable uniting atmosphere of a sporting occasion is something you want to experience, catching a home game at Soldier Field is another top thing to do. It is the home of the city’s NFL franchise, the Chicago Bears, and has been used for this purpose since 1971. It has been used in both the men’s and women’s soccer World Cups.
The iconic nature of the stadium, which was actually built in the 1920s, extends to its status as both the oldest and smallest stadium in the NFL. As a former National Historic Landmark, it is a venue loved by sports fans across the nation. You now have the perfect opportunity to add it to your Chicago itinerary. Make sure you do.
Willis Tower
Built in 1974 and formerly known as the Sears Tower, Willis Tower remains Chicago’s tallest building. It stands a colossal 1,451 feet (or 442 meters) tall, piercing the Chicago skyline to stand out as a truly iconic landmark. Its 103rd floor skydeck offers incredible panoramic views of the city, which is especially ideal for keen photographers.
Similarly, it forms a significant part of the iconic Chicago city views seen from ground level. Whether looking across the water or up close, the Willis Tower is sure to grab the attention. While it certainly stands out as an attraction for tourists, its historical context and awe-inspiring size make it a must-see for locals too.
Tilt 360
Another iconic tower is Tilt 360. While the deck is “only” 94 floors up, you are still treated to truly spectacular views of the city you now call home. The 360-degree panoramic views give you a whole different perspective of the city, and the excitement is elevated to another level thanks to the fact you lean out over the glass.
Looking directly down on the street from that height can get the heart racing. Thankfully, you can calm yourself down by grabbing a drink and something to eat at the on-site cafe. Tilt 360 observation deck is found at 875 N Michigan Ave, meaning a trip here can be combined with a variety of additional experiences.
AIRE Ancient Baths
As a local, you’re not just looking to enjoy historic architecture and see tourist attractions. Hotspots that enhance your general lifestyle are equally important, and AIRE ancient baths are an idyllic spot to indulge in a range of spa treatments. You will leave the iconic looking and feeling rejuvenated.
In addition to individual treatments, the venue is known for its couples massages. It’s the perfect date for busy professionals in Windy City. The professional treatments are completed in truly peaceful environments featuring beautiful architecture, soothing sounds, and a generally tranquil atmosphere. Bliss.
Chicago Pizza
Chicago is synonymous with world-class deep dish pizza. In fact, the dish plays an epic role in the city’s history. So, when you tuck into a pizza at one of the city’s many, many pizza restaurants, you get a true taste of life in Chicago. From take outs on street corners to historic eateries and luxury restaurants, it’s love at first bite.
It’s impossible to pick one place to try deep dish pizza in Chicago. Every venue has its unique spin on the dish but they are all defined by the high-walled, buttery and flaky crusts as well as the “upside down” cheese first, tomatoes second assembly. You can’t live in the city and not get to love this epic take on pizza.
DuSable Black History Museum
Many of the museums in Chicago have comparable venues across the U.S. and beyond. However, the DuSable Black History Museum is the first of its kind, celebrating the history and culture of African Americans. It underlines Chicago’s importance to equality movements, as well as the significance of diversity to the city.
A number of events and exhibits are on show at the venue, including a dedicated 100 Years of Black History Month exhibition. Founded in 1961 and operating from its current 740 E 56th Pl location since the 1970s, it is an iconic venue within the city’s history, culture, and art scene. Locals can gain a lot from visiting the museum.
Broadway
Chicago and broadway entertainment go hand-in-hand. The famous musical that takes its name from the city remains one of the most popular shows, and there is nothing quite like seeing it in Windy City. However, there are dozens of shows on daily at some of the country’s most iconic venues. It would be foolish to miss out on them.
Locals can often secure discounted tickets for iconic venues like the Auditorium, James M. Nederlander Theatre, Cadillac Palace Theatre, CIBC, and Broadway Playhouse at Water Tower Place. World-class entertainment meets iconic venues, making it impossible not to cherish living life in America’s third-largest city.
Additional Things To Do In Chicago
In truth, the list of attractions in Chicago goes on and on. Centennial Wheel, Skating Ribbon, live entertainment venues, Tribune Tower, and the Children’s Museum are just some of the options to consider. Of course, as a local, you can also enjoy daily facilities like gyms and sporting activities.
From daily comforts to memory-making attractions, you’ll never be short of options.
What To Do In Chicago: FAQs
Does Chicago Have A Lot To Offer Families?
There are loads of family-friendly attractions in Chicago ranging from interactive museums to zoos, beaches, lakefronts, and more. Lincoln Park, Bridgeport, and multiple neighborhoods in the suburbs provide a great quality of life for families too.
What Are The Best Free Attractions In Chicago?
As well as paid attractions, Chicago boasts several great free attractions, although some include paid optional extras. Popular outlets include Millenium Park, the Magnificent Mile, Cloud Gate, Navy Pier, Chicago Riverwalk, and Chicago Cultural Center.
Which Neighborhoods Are The Best For Things To Do In Chicago?
Chicago is blessed with top attractions across the city. Head to River North for dining and nightlife, Lincoln Park for nature, West Loop for food, Wicker Park for arts and creative, or Pilsen for cultural experiences.
Is Chicago A Good Place To Live For Renters?
Absolutely. As well as a diverse range of attractions and entertainment, Chicago is a vibrant city with lower costs than other big cities like New York. This is further supported by a thriving job market in the finance, tech, and healthcare sectors.
