Chicago is a vibrant city with so much to do that it would take practically a lifetime to experience it all. Whether you’re looking for cultural attractions like world-class museums, to shop till you drop, catch a sports game or a concert, or take part in the thriving nightlife, you’ll find plenty here. Of course, dining is wide-ranging too, with stands for picking up one of the city’s world-famous hot dogs, restaurants serving iconic Chicago-style deep-dish pizzas, and Michelin-starred venues worthy of a celebration.
With the cityscape flanked by Lake Michigan, many hotels showcase beautiful lake views, and there are even options for hotels with hot tub in room in Chicago. The Langham has rooms with private spa tubs where you can gaze out at the iconic architecture, but we also love the Italian-inspired Villa D’Citta, where you’ll have your own private hot tub.
But no matter where you stay in Chicago, when it comes to putting together an itinerary that makes the most of your time, you’ll want to put at least a few of these things to do on your list.
Take in a Panoramic View from the 360 Observation Deck
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The John Hancock Building’s 360 Observation Deck sits at approximately 1,000 feet above the Magnificent Mile (Michigan Avenue) on the 94th floor, providing a 360-degree vista of Lake Michigan, the city’s skyline, and even four neighboring states. If you’re looking for a thrill, don’t miss the TILT, a ride that tilts guests out and over the city from the observation deck. There’s a cafe and bar here too, with an impressive selection of cocktails and a front-row city for taking in Chicago’s best view.
Insider tip: Start your visit to Chicago with a visit to this observation deck to get a perspective of the city’s layout, along with the breathtaking view.
The Magnificent Mile – Best in downtown Chicago
The Magnificent Mile is the section along Michigan Avenue that stretches from the bridge spanning the Chicago River to Oak Street’s northern point. This is where shopping enthusiasts come to work out their wallets. The 13-block area hosts nearly 500 stores, primarily large retailers, including well-known venues like Bloomingdale’s, Nordstrom, and Saks Fifth Avenue. Closer to Oak Street, you’ll see designer boutiques such as Dior, Prada, and Hermès, where it’s not uncommon to run into a professional athlete or another type of celebrity dropping some serious cash.
For some quirky, independent venues, head slightly off the main street, onto the smaller side streets, and you’ll discover more unique treasures. If you want to add color to your home or buy a cool gift, look for Colores Mexicanos, which has some great Mexican decor. There are multiple landmarks too, like the neo-Gothic Tribune Tower, the historic Chicago Water Tower, the 100-story John Hancock Center, and the Wrigley Building skyscraper. In between, you’ll find trendy restaurants and high-end hotels. Wear your comfortable walking shoes to fill a day exploring it all.
Mag Mile landmarks and the nearby riverwalk are essential things to do in Downtown Chicago.
Navy Pier – Most fun thing to do
Navy Pier bundles some of the most fun things to do in Chicago, from the Centennial Wheel to lakeside theater and summertime concerts. The lakefront Navy Pier dates back to 1916 and is considered a must-visit with a wealth of attractions. It was originally designed as a hub for freight boats and events like expos and conferences, but today, you’ll find highlights like the nearly 200-foot-high Ferris wheel with enclosed gondolas showcasing 360-degree views of the lake and the city. Other highlights include a carousel, a wave swinger, a mini-golf course, a funhouse maze, the Chicago Shakespeare Theater, the Chicago Children’s Museum, and an outdoor stage for entertainment, including live music from May through September.
You’ll find many retail venues for shopping and plenty of tasty eats, including grab-and-go items like classic Chicago-style hot dogs and sit-down restaurants. The iconic Harry Caray’s Tavern on the waterfront is especially popular for dining with a beautiful lake view.
Spirit of Chicago Cruise – Best thing to do for couples
In addition to all the fun on the pier, you can take the Spirit of Chicago dinner cruise departing from it for an evening out on the water. It all begins just before sunset, perfectly timed for watching the sun go down over the city skyline. During the two-hour excursion, you’ll have your own private table for dining on dishes from the buffet-style menu, including fresh, seasonally inspired dishes with mains such as Atlantic flounder, sesame chicken, and braised beef short ribs. There’s also a DJ and dance floor, and interactive games like giant Jenga and shuffleboard. Sunset sailing, a private table, and skyline views make this one of the best things to do in Chicago for couples.
Chicago Botanic Garden
Spread over 385 acres on nine islands, the Chicago Botanic Garden is made up of more than two dozen gardens and four natural areas. One of the top science conservation centers and living museums in the city, it includes over 2.4 million plants with a blooming rose bush, one of the highlights, exemplifying just how hardy this species is, with its ability to endure Chicago’s severe weather. The bonsai collection is also impressive, as one of the best that can be seen anywhere. It includes nearly 200 bonsai plants, one of which is a Japanese white pine gifted by bonsai master Susumu Nakamura.
Lincoln Park Zoo – Best free thing to do
Established in 1868, Lincoln Park Zoo is one of the oldest zoos in North America. It’s also one of the few in the entire country that you can visit for free. There are over 1,100 animals that represent almost 200 different species, with highlights including the Regenstein Center for African Apes and Regenstein African Journey, which houses gorillas and other African wildlife. The Kovler Lion House, the Sea Lion Pool, and the children’s zoo are just a few of the other popular spots.
Check the zoo’s event calendar before your visit, as there are often seasonal and other special events like Fall Fest. It’s free to attend and includes all sorts of fun for harvest time, like pumpkin picking and pumpkin carving demonstrations. Plus, there is live entertainment, a fire pit where you can warm up while toasting S’mores, and lots of fall color in the gardens, providing some fabulous photo ops. During the winter, the Zoo Lights display is also worth visiting, drawing many visitors every year.
With free admission year-round, the zoo ranks among the top free things to do in Chicago for all ages.
Delve Into the Booming Art Scene
Chicago is highly acclaimed for its art scene. One of the liveliest in the country, it would be easy to create a trip focused on art alone, starting with the exceptional Art Institute of Chicago, located downtown by Millennium Park. Named by Tripadvisor readers among the “Best of the Best” US attractions of 2025, it sits within a Beaux Arts building flanked by bronze lions that have long been a symbol of the city. Of course, it’s what’s inside that most come for, with one of the finest collections of Impressionist works in the world. Works by icons like Picasso, Dali, and Warhol are just a few of the most notable. The vast Asian collection, a photography collection spanning the history of the medium, and a medieval armory are all worth browsing too. If you have any interest in architecture, don’t miss the quirky Thorne Miniature Rooms.
They capture architecture worldwide from the 13th to the 20th century in dollhouse proportions.
The Museum of Contemporary Art is a must for modern art enthusiasts, holding one of the nation’s most extensive collections. Plus, it hosts major touring exhibits and film screenings. Yet another highlight is the Loyola University Museum of Art, with highlights like the Martin D’Arcy, S.J. Collection, with medieval, Renaissance, and Baroque art.
Visit Shedd Aquarium – Best with kids
One of the best institutions of its kind you’ll find anywhere in the world, Shedd Aquarium is popular among families with children, but it’s a delight for all ages. There is a wide variety of exhibits, such as the Amazon, the Pacific Northwest, and the Great Lakes, but it goes way beyond simply looking at marine creatures through the glass. There are hands-on experiences like touching starfish and stingrays, or even feeling the scales of a lake sturgeon. The Polar Play Zone provides interactive exhibits for the little ones, including a kid-sized submarine, and there are even unique encounters like the shark feedings and the chance to be a “Trainer for the Day.”
There’s a rather terrifying predator shark tank where some come to face their fears, and adorable penguins that you can watch waddling around. Larger sea mammals can be seen here too, including sea lions, dolphins, and beluga whales, with the aquarium assisting in rescuing and rehabilitating orphaned or stranded belugas. The whales can be seen in the Abbott Oceanarium aquarium exhibit, a 3-million-gallon habitat which was designed to recreate the Pacific Northwest’s coastal ecosystem, including the region’s cold, saltwater environment. Presentations and shows starring the marine animals are hosted here as well. Hands-on touch pools and the Polar Play Zone make Shedd ideal when you’re planning things to do in Chicago with kids.
Cheer on the Home Team at Wrigley Field
One of the most storied landmarks in the city, Wrigley Field is an icon. A visit is on the bucket lists of many baseball fans, with millions flocking here just to get a photo in front of its legendary marquee, whether rooting for the Cubs or not. The very first National League Baseball game was played right here in 1916, which means a visit or catching a game here brings the chance to witness baseball history. While the best way to experience it is to cheer on the home team alongside the passionate Cubs’ fans, if you’re here outside the season, there are plenty of other options, including guided tours where you’ll get to go behind the scenes while learning more about the stadium’s past and some of the most legendary players.
The ballpark serves as the anchor of the Wrigleyville neighborhood, which has many venues of its own, including the adjacent outdoor plaza, Gallagher Way, that hosts events for the kids, movie nights, markets, fitness classes, and more. There are several bars, restaurants, and the Hotel Zacary is here if you want to stay right on-site.
Embark on a Guided Walking Tour Through Oak Park
If you’re a history or architectural enthusiast, you won’t want to miss the chance to explore the Oak Park neighborhood. It’s home to the world’s largest collection of Frank Lloyd Wright-designed buildings. It’s possible to take a self-guided audio tour with narration revealing more about the structures’ history. Or, even better, take a guided tour with an expert.
There are multiple options available, but I highly recommend taking a tour via the Frank Lloyd Wright Trust, which includes the Wright Home and Studio. You’ll explore the birthplace of the architect’s vision for new American architecture, tracing his early years from the studio where he conceived the Prairie-style design to the incredibly well-preserved private Prairie homes. Wright designed dozens of these homes between 1900 and 1920. As the trust notes, it’s an opportunity to “witness the evolution of Wright’s architectural design philosophy in the neighborhood where the architect lived and worked.”
Hit the Lakefront Trail
The Lakefront Trail travels 18 miles, following Lincoln Park and six miles of Lake Michigan shoreline. It’s the perfect place to walk, jog, or cycle, with multiple venues renting bikes that include helmets and locks if you can’t bring your own. The trail passes several sandy beaches, vast parkland, a bird sanctuary, the zoo, and a rock garden. There are also vantage points for taking in spectacular views of the Chicago skyline and numerous places to stop, grab a bite, or simply rest. You might even pedal around to some of the top cultural attractions with many accessible from here, like the Theater on the Lake in Lincoln Park, and the Museum Campus toward the southern end, which includes Shedd Aquarium, Adler Planetarium, and the Field Museum.
Need easy things to do in Chicago today?
Rent a bike and follow the Lakefront Trail for skyline views and beach stops.
Paddle along the Chicago River or Lakefront
Another fun way to get active while soaking up fantastic views is to paddle along the Chicago River or the lakefront. There are many different guided kayaking tours available, including historic tours, sunset, and even nighttime excursions hosted by Urban Kayaks. You’ll glide across the water right through the heart of the city on the river, or along Lake Michigan, which includes circling the Museum Campus with Shedd Aquarium, the Field Museum, Soldier Field, and Adler Planetarium.
If you take the 90-minute skyline paddle on Lake Michigan, you’ll get a unique perspective on many of the major tourist sites without having to deal with the crowds, including the Navy Pier and Grant Park. I also like the after-dark tour on the river. On this tour, you’ll be able to admire the illuminated Merchandise Mart with its rotating digital art displays that are projected onto the building.
Chicago’s Chinatown packs a full afternoon of culture, food, and riverfront views into just a few walkable blocks. Enter through the Chinatown Gate and stroll Wentworth Avenue past herbal shops, bakeries, and bustling dim sum halls. Detour to Ping Tom Memorial Park for skyline photos and a breather by the water, then pop into the Chinese American Museum of Chicago to add context to what you’re seeing (and tasting).
Don’t miss the Nine Dragon Wall and the Zodiac Plaza at Chinatown Square for quick, colorful photo ops. When hunger hits, join the dim sum carts at MingHin Cuisine or order hand-pulled noodles at a casual spot nearby, followed by bubble tea or a traditional tasting at a local tea shop. As part of your itinerary of things to do in Chinatown Chicago, time your visit for late morning into early afternoon to catch peak energy—and bring cash for bakeries and snack counters that may not take cards.
Insider tip: hop the Chicago Water Taxi to/from Chinatown for a cheap mini–boat tour with great skyline angles.
Find Your Favorite Deep-Dish Pizza
When it comes to food in Chicago, the city is most renowned for its deep-dish pizza. While it’s a bit of a controversial topic here, many say it was invented in 1943 at Uno Pizzeria by founder Ike Sewell, including the business itself. However, a report from the Chicago Daily News dated to 1956 disputes that, writing that it was the original pizza chef at Pizzeria Uno, Rudy Mainati, who developed the recipe.
Regardless of the true inventor, there’s no doubt that it’s the most iconic dish in Chicago, with a thick crust that resembles a pie more than your typical flatbread pizza. Some say Uno’s still makes the best in the city, but it’s up for debate, which means you’ll need to try at least a few from various pizzerias to determine your favorite. Insider tip: Pequods definitely gives Uno Pizzeria a run for its money – as you’ll see by the long line where patrons wait as long as two hours for the chance to enjoy a buttery crust pie that oozes with gooey mozzarella and a mouthwatering tomato sauce. Lou Malnati’s and Gino’s East both make exceptional pies as well, which means you’ll need to decide for yourself!
Check Out a Farmer’s Market – Best thing to do on weekend
One of the tastiest things to do in Chicago this weekend is browsing Green City Market and picnicking in Lincoln Park. The many foodies and talented chefs in Chicago have access to a remarkable bounty of fresh products, including fruits, vegetables, dairy, and meats that come from rural communities in the surrounding area. As the population is so diverse, ethnic ingredients are easy to find too. There are over 60 different farmers’ markets in the city that locals and visitors alike can take advantage of, so while it can be hard to know where to start, the largest is the Green City Market. It’s been around for over two decades, originally set up with only a handful of vendors in an alley near the Chicago Theatre.
Today, you’ll find nearly 60 vendors here alone on Saturdays at the south end of Lincoln Park. It’s the perfect place to sample a wide range of foods while participating in a huge social event. On a sunny day, many local families come to pick up ingredients for a picnic on the grass, often with their dogs.
Insider tip: There are so many enticing food stands here, but it’s hard to beat Gayle V’s Best Ever Grilled Cheese. While it’s particularly famous for its grilled cheese sandwiches on house-baked sourdough, the chili and tacos are amazing too.
Check Out the Skyline from North Avenue Beach
If you visit during the summer, you should really make your way to North Avenue Beach. Located in Lincoln Park, it’s a hotspot for sunbathing and swimming, while the lakeshore path here is filled with walkers, bikers, and rollerbladers. Not only is it a popular place for people watching, but it’s another one of the best places for a skyline view.
Catch a Live Show – Best for adults
Chicago is home to nearly an endless list of venues hosting live music, including intimate spots and establishments where you can catch a big-name artist. One of the best thing to do in Chicago as an adult, head to the Green Mill, which Conde Nast Traveler named among its list of the very best bars in the city, noting it as “old-school Chicago at its finest” and a “legendary spot on the nightlife circuit.” It’s been here for more than a century, and as it’s so popular, you’ll need to arrive early for a good seat, available only on a first-come, first-served basis.
Just a few of the other notable spots include Rosa’s Lounge, which hosts live blues that attracts a diverse crowd. It also has a full-service bar for sipping while listening to the sounds of bands like Billy Branch & the SOB. Thalia Hall is a historic landmark, initially designed as an opera house that opened in 1892. Today, you can see renowned musical acts in the ornate concert hall.
Looking for things to do in Chicago tonight?
Check Thalia Hall’s calendar or book an evening architecture or dinner cruise.
St Paddy’s Day Celebration
It’s worth planning a trip around Chicago’s St. Paddy’s Day celebration as one of the best in the country. The river is even turned green just for the event. Arrive early, and you can watch the transformation, which starts with an orange hue before some leprechaun magic makes it a brilliant emerald green, reminiscent of Ireland’s lush hills and mountains. The celebration includes a parade that marches from Balbo Drive to Monroe Drive, with Irish step dancers, bands, bagpipers, and elaborate floats. Green beer is ever-flowing, and nearly everyone will be wearing the color, so take heed and blend in with the locals!
Keep in mind that the Irish take the name seriously, including those who are likely to be here during the event, so whatever you do, when referring to the holiday, remember this: St. Paddy’s is derived from the Irish name Pádraig, while Patty is the common nickname for Patricia.
Bonus Day Trips & Weekend Getaways from Chicago
As mentioned, it would take practically a lifetime to see and do it all in Chicago, but if you want to escape the city for the day or the weekend, consider one of these destinations:
- Starved Rock State Park (2 hours) – hiking trails for viewing waterfalls and canyons
- Indiana Dunes National Park, Indiana (50 minutes) – over 50 miles of trails leading through woodlands, prairie, wetlands, and shifting sand dunes
- Andersonville (20 minutes) – known for its Swedish heritage with a Swedish American Museum, diverse dining, and shopping
- Midewin National Tallgrass Prairie (80 minutes) – protected natural prairie habitat with a small herd of bison and other endangered or threatened animal species
- Rockford (100 minutes) – A city renowned for its gardens, home to the Anderson Japanese Gardens and Klehm Arboretum & Botanic Garden, with a children’s garden, themed specialty gardens, and walking trails
- Milwaukee, Wisconsin (1 hr, 45 minutes) – A top spot for beer lovers with over 40 breweries
- Lake Geneva, Wisconsin (90 minutes) – Outdoor adventures, beaches, a waterpark, museums, & much more
For those with extra time, be sure to check out our top weekend getaways from Chicago for even more ideas!
