Mark Twain famously said about Chi-Town, “She is novelty; for she is never the Chicago you saw when you passed through the last time.” Twain’s quote is still true today. This city can and does change on a dime. You can visit again and again and still find awesome new things to see and do. The Midwest’s largest city, Chicago’s history dates back to 1830. In 1871, one-third of the city was destroyed by fire, but it bounced back even stronger than ever.
Chicago is the site of the very first skyscraper, the birthplace of Chicago jazz and blues, and the former home of Al Capone’s multi-million-dollar bootlegging and gambling ring. With its amazing skyline, historic architecture, landmarks that wow, and world-class eats, arts, and entertainment, it’s no wonder the Windy City is a magnet for travelers.
Even better, it’s a friendly city that welcomes visitors with a smile. If you’re ready to dive in to great things to do in Chicago, then start brainstorming with this handy guide.
Best Chicago Tourist Spots
More than 50 million tourists flock to Chicago every year, which shouldn’t come as a surprise, since there are so many cool things to see and do. From world-class museums to massive parks and mouthwatering eateries, Chicago has it all.
Like most big cities, Chicago boasts a motherlode of museums. The entrance of the Art Institute of Chicago, with its grand staircase and bronze lions guarding the door, is also where hundreds of Chicago marriage proposals happen every year.
And the museum itself is rated by U.S. News & World Report as one of the city’s top attractions. It’s home to more than 300,000 works of art — everything from ancient treasures to modern art. It’s also home to one of the biggest collections of impressionist art. Here are a few other top museums:
The Museum of Science & Industry has more than 35,000 artifacts and loads of hands-on exhibits that are all about the city’s history of creativity and knack for new ideas.
The Museum of Contemporary Art is home to one of the nation’s most mind-blowing art collections, highlighting works by local artists, up-and-coming talent, and the greats.
Adler Planetarium is part museum, part out-of-this-world experience. Check out the Sky Theater, with its incredible high resolution, and the Mission Moon exhibit that brings the space race to life.
Take it outside and check out some of the city’s famous parks. Millennium Park is right inside the Loop, just a quick walk from the Art Institute. Covering more than 24 acres, this city park is home to some awesome landscaping and public art, including the “Cloud Gate” sculpture — also called, “The Bean.” The park gives seasonal tours of the architecture and gardens.
The impressive Crown Fountain, designed by Spanish artist Jaume Plensa, features 50-foot towers and a reflecting pool that make a super-cool backdrop for selfies and family photos. It’s a great park for chowing down on a picnic and sitting back for some people watching.
Another famous Chicago green space is Grant Park, which a lot of folks call the city’s “front yard.” This 319-acre park is home to other top go-tos like the Field Museum and Shedd Aquarium. It’s also loaded with open fields, baseball diamonds, walking paths, and landscaped gardens. The heart of the park is its showpiece, Buckingham Fountain, one of the world’s biggest fountains. In warm weather, 133 jets shoot water up to 150 feet in the air for about 20 minutes at the top of every hour.
There’s no better way to see this amazing city than from high up in the sky. When it comes to picking things to do in Chicago, observation decks are unbeatable. Three main spots serve up the best views when you want to get a birds-eye look at Chi-Town: Chicago Temple’s Sky Chapel, the Skydeck/Ledge at Willis Tower, and 360 Chicago in the John Hancock Building. As a bonus, Sky Chapel is inside the tallest church on earth, Chicago Temple. The chapel is 400 feet above the sidewalk and delivers eye-popping city views.
When it comes to thrilling observation decks, 360 Chicago and Skydeck are neck and neck. 360 Chicago’s observation deck soars 1,000 feet above the Magnificent Mile. And, yep, it offers 360-degree views of Chicago’s skyline. One of its newest draws, Tilt, is billed as the highest thrill ride in Chicago. This enclosed platform moves to tilt you out over the street from the 94th floor.
No slouch either, Willis Tower’s Skydeck also serves up city views that don’t quit. The thrilling Ledge attraction lets you safely step out — it seems, into the air — to eyeball the city from 1,353 feet above the street.
Chicago has a sizzling hot food scene, and both locals and tourists love to sink their teeth into all the flavors the city serves up. You can count on the famous hotspots dishing up classic Chicago eats. Dig in to Chicago-style hot dogs at Portillo’s or Franks ‘n Dawgs, or chow down on deep-dish pizza at classic joints like The Original Gino’s East of Chicago or Giordano’s Pizza. Here are a few more of the city’s hottest eateries:
Pizano’s Pizza & Pasta has the perfect selection of everything Italian, from thin crust, deep dish, and freshly prepared pasta dishes. A trip to Chicago wouldn’t be complete without a taste of their famous pizza!
For a hearty meal at community-style tables, head over to Smoque BBQ. With ribs, brisket, pulled pork, and mini-sandwiches for the kids, it turns out you don’t need to head down south for good BBQ after all!
Little Goat Diner is a cool eatery that serves tasty dishes that will have every member of your family ready for seconds! This spot takes a creative, gourmet approach to favorite comfort foods, including ooey gooey cinnabons, grilled cheese sandwich with apple-tomato relish, and goat chili cheese fries.
Best Kid-Friendly Attractions in Chicago
Chicago is a great place for a family vacation. The huge choice of kid-friendly hotspots has something for every member of the family, so everyone goes home happy.
Kids and zoos go together like peanut butter and jelly, and Chicago has tons of places for animal-loving tykes to get close up to critters. Although the Chicago Zoological Society’s Brookfield Zoo is outside the downtown hub, it’s totally worth the quick drive or Metra ride to get to this gem in the western suburb of Brookfield.
An all-inclusive pass gets the whole gang in to all the zoo’s attractions, including the motor safari tram — a huge hit with kids of all ages. Ride it round trip, or take it to each of the four stations to explore top zoo spots like the award-winning Hamill Family Play Zoo, where kids can touch stuff, play, build, and explore with dress-up, crafting, and play-acting. The nearby Hamill Family Wild Encounters is a fave with both kids and adults. Here kids can have tons of hands-on fun petting and feeding animals, including goats, red pandas, wallabies, and reindeer.
If you want to explore closer to downtown or check out another zoo, it’s hard to beat the world-famous Lincoln Park Zoo. It’s home to cool things to do like a dazzling light maze filled with 30,000 lights, a penguin encounter where kids can get a close look at African penguins, and the Sea Explorer 5-D show that takes the whole clan on a virtual submarine tour.
You can also zip over to Shedd Aquarium, an indoor aquarium that sits near the shores of Lake Michigan. It’s home to 32,000 animals in exhibits like Caribbean Reef, Polar Play Zone, Abbott Oceanarium, and Amazon Rising that bring different parts of the underwater world to life.
Chicago Children’s Museum tops best-of lists for the 10 and under crowd, but lots of the exhibits are also a hit with older kids. Case in point: The Tinkering Lab is a DIY workshop with real materials and tools that let kids use gears, chutes, and other parts to make their very own gizmos. Younger kids get in on the action in the Early Learning Nook, with tools and hands-on wall panels for safe, fun learning. Don’t miss the ginormous dinosaur expedition, the water playground, and Treehouse Trails, where kids can explore a cool forest.
Keep these other fun kids’ museums on your radar:
The Field Museum: Kids love this natural history museum that makes science fun and cool. Get the details on dinosaurs, watch 3-D movies in the museum theater, and get hands-on in the Crown Family PlayLab.
Skokie Exploratorium: Two words describe the larger than life magic inside: Lite Brite. The museum has a huge Lite Brite wall that wows the kid inside everyone. It also has a theater where kids can dress up, a stream where they can go “fishing,” and a play area that’s perfect for burning off extra energy.
Peggy Notebaert Nature Museum: On a nice day, there’s nothing better than checking out the Judy Istock Butterfly Haven, where these flying beauties often land on you from all directions. Kids also dig the climbable spider web and the underground cave.
Not all tours are dreamed up with kids in mind. When tots are in tow, look for tours that keep things light and fun. Like, who doesn’t love a scavenger hunt? Big City Hunt’s self-guided scavenger hunt tour takes you on a two-hour scavenger hunt around the Loop, one of the city’s major arts and shopping hubs. Along the way, you have to solve puzzles, complete challenges, explore historic spots, and work together as a team.
Families with older kids rave about the Millennium Park Segway Tours for kids 12 and older. Zoom on a Segway through this pretty park with its lakefront and skyline views. Or hop on the Chicago Architecture Foundation’s River Cruise. Even if the kids don’t care about the architecture, they’ll be psyched to boat down the river.
Navy Pier is a long-time Chicago go-to and home to some awesome rides, including the 200-foot tall Centennial Wheel, which delivers killer views of the city and Lake Michigan. The Wheel is open year-round, and during warm weather, Pier Park kicks into high gear with other rides and fun stuff to do, including:
Remote Control Boats
Best Free Things to Do in Chicago
Whether you’re planning a weeklong vacation or a quick getaway, having a blast in Chicago doesn’t have to break the bank. Luckily, the city is loaded with amazing stuff to do and see to help stretch your budget without losing out on fun. If you’re on the lookout for free things to do, then think about one or more of these top picks.
Take a deep dive into the arts without spending a dime when you visit some of the city’s free exhibits and museums. The Smart Museum of Art is chockfull of works by greats like Frank Lloyd Wright, Ansel Adams, Picasso, Dega, and Mattise. Plus, the Renaissance Society at the University of Chicago has free art history programs. Other free spots that will grab your attention include these gems:
National Museum of Puerto Rican Arts and Culture: This Humboldt Park museum is right in the heart of the city’s Puerto Rican community. It was founded in 2000 with the goal of highlighting Puerto Rican culture through its exhibits and programs.
National Veterans Art Museum” Every bit of the artwork at the National Veterans Art Museum is created by veterans. The museum’s mission is to provide a space for civilians, current military members, and veterans to talk about war and the impact of combat.
National Museum of Mexican Art: The collection at this museum spans 3,000 years of work to showcase Mexico’s rich culture. Loads of the exhibits from here travel around the world to other museums.
The Chicago Cultural Center: This free center is the first of its kind in the U.S. It delivers all kinds of art programs that are a hit with locals. The Tiffany dome — the biggest in the world — might be its coolest feature.
Free Walking Tours
Yup, self-guided tours of the city are one free option, but having a guide can really give you a better feel for the city and help you find the hidden gems, historic highlights, and nooks and crannies you might not get to on your own. Most free guided tours ask for donations but don’t charge specific fees. Some of the top outfits with free walking tours of Chicago include:
Free Tours by Foot runs tons of cool tours, including the North Loop and Millennium Park, Riverwalk History, Gold Coast, Movies and Filming in Chicago, Blues and Gangsters, and Architecture Tours.
Free Chicago Walking Tours is a seasonal tour company serving up two-hour tours that zoom in on the Total Loop, Lincoln Park, Haunted Ghosts, and the Magnificent Mile.
Chicago Greet has year-round tours you can tailor to whatever you’re into. You register online, meet up with your Greeter downtown, and then head out on your two-to-four-hour guided sightseeing walk.
Commune with Nature
It doesn’t cost anything to head outside and play in one of Chicago’s beautiful parks. Maggie Daley Park, set in Grant Park’s northeast corner, has become a local fave. Walking trails and a great play garden mean there’s plenty to do, and the design and attractions are buzz-worthy. Note that some of the activities in the park have a small fee. One is the climbing wall; the low charge includes equipment rental.
To really soak up nature, think about a trip to Lincoln Park Conservatory, a year-round green house full of beautiful plants and flowers. For a winter bonus, it feels like walking in paradise even in the cold. The Garfield Park Conservatory, which is made up of six different greenhouses and two exhibition halls, is the ideal place to see and learn about rare plants.
Take a Walk
Chicago is home to several scenic walks with views that look like a million bucks — but don’t actually cost a cent. The Chicago Riverwalk is one of the prettiest areas to stroll. Wander along the Chicago River with skyscrapers, public art, and live music in the background. It’s also a great way to check out the amazing designs of some of the city’s coolest buildings.
Walking the Magnificent Mile serves you scenery of a totally different kind. This stretch of Michigan Avenue that runs from the Chicago River to Lake Shore Drive is home to some of the city’s top landmarks, swanky hotels, and all kinds of eateries. It’s also home to about 460 different shops, ranging from major department stores to high-end designers.
Best Things to Do in Chicago in the Summer
Summer is a sweet time to travel. You might even find yourself doing a happy dance when you think of rocking a summer trip to the Windy City.
Hit the Beach
You might not think of beaches when you think of Chi-Town, but since it’s right on the shores of Lake Michigan, it’s an awesome place to hit the sand, splash around, and have some fun in summer. Some of Chicago’s best beaches include Montrose Beach, one of the biggest and most popular spots. If Fido is road-tripping with you, book it to the dog-friendly beach on the north end. When you get hungry, grab a bite at The Dock, the full-service beach restaurant that also hosts a weekly reggae jam. Put these other fab beaches on your shortlist:
Oak Street Beach is a popular spot for sunning, playing volleyball, and catching great views of the skyline.
South Shore Beach sits within the South Shore Cultural Center, which has its own nine-hole golf course, a solarium, and a nature sanctuary next door with wetlands and a butterfly garden.
North Avenue Beach is an easy walk from Lincoln Park and tops locals’ best-of lists, partially due to its onsite restaurant, volleyball courts, and skyline views.
Ohio Street Beach boasts a mile-long stretch of shallow water that’s a hit with swimmers.
31st Street Beach on the South Side has a restroom, concession stand, lifeguard, and a playground that’s perfect for kids when they need a break from building sand castles.
Attend a Street Festival
Chicago’s street festival scene starts heating up in May with the Randolph Street Market Festival, held on the last weekend of the month, jam-packed with more than 200 different vendors who sell clothing, antiques, housewares, and food. During the summer months, the festival opens an outdoor shopping area.
June is a month that buzzes with neighborhood events like Lincoln Park Greek Fest and Andersonville Midsommarfest, a legendary street fair that has wowed Chicagoans with its Swedish traditions for more than 50 years. July is all about the Windy City Ribfest in the early part of the month, and the Southport Art Festival in mid-July in the Southport Corridor. In August, hot city happenings include the Ginza Holiday Festival, which highlights Japanese culture and food, and the Chicago Hot Dog Fest, complete with live music and Vienna beef hot dogs.
Head to the Park
During the summer months, plenty of Chicago’s parks come with extra perks. The city’s Park District publishes its schedule for Movies in the Parks, which shows hundreds of flicks in parks all over the city. Pack a picnic and join the locals at Millennium Park’s Jay Pritzker Pavilion for a night of free music during the Summer Concert Series, where all kinds of music-makers from around the country hit the stage.
When Chicago warms up after its monster winters, it’s no shock the city is all about chowing down outside during late spring and summer. Some of the city’s best outdoor chow houses include the laid-back Parson’s Chicken and Fish in Logan Square, which boasts a big patio filled with cheerful umbrellas, picnic tables, ping-pong tables, and plenty of string lights to add magic to the summer nights. Belly up for must-try menu picks like the crave-worthy hush puppies.
Gather is another hot choice. This Lincoln Square gem boasts a 40-seat, covered outdoor patio and a menu of dishes made for sharing. Standouts include the house-made whipped ricotta on baguettes and the steak tartare. If you’re looking to dig into a Chicago dog or Italian beef in a fun, laid-back outdoor spot, Portillo’s second location on the West Loop might just fit the bill.
From stellar museums and zoos to out-of-this-world outdoor attractions, Chicago hits all the highlights for a first-rate vacation.
What are you most psyched about doing in Chicago? Tag Dollar Car Rental in your favorite Instagram photos so we can check out your favorite spots!