There are few cities more spectacular than Chicago. Nestled on the banks of Lake Michigan, Chicago has everything from sandy beaches and luxury shopping districts to vibrant cultural scenes and art galleries and there is something for everyone.
The Windy City is a fabulous year-round destination for those who crave art, culture, adventure, world-class restaurants, and hotels. From fancy shops like Tiffany & Company on Michigan Avenue to quiet neighborhoods like Andersonville and Hyde Park, the city of Chicago offers an unequaled travel experience. With so much to see and do in Chicago, it’s hard to fit it all in one trip! Here are my favorite things to do in Chicago, including where to eat!
Best Things to Do in Chicago
Chicago is a very walkable city, especially in downtown areas like the Loop, River North, and along the Magnificent Mile. Chicago is bike-friendly, with many bike lanes and trails, especially along the Lakefront Trail. The city’s bike-sharing program, Divvy, offers an easy and affordable way to rent a bike for short trips. To get downtown from the airport, book a private airport transfer
Part One – Things to Do in Downtown / Waterfront
Looking for more information on Chicago? Read our article about the Best Places to Stay in Chicago.
1. The Bean – Millennium Park and the Cloud Gate
The Bean at Millennium Park is perhaps one of the most iconic sculptures in Chicago, or at least that’s how most visitors describe it. It’s actually named the “Cloud Gate”, created by the world-famous sculptor Anish Kapoor. Visit the beautiful Millennium Park to take advantage of a wonderful photo op with The Bean. Its gleaming mirrored finish makes a beautiful backdrop as it seems to distort the city’s skyline creatively.
Other Things to Do at Millennium Park
Millennium Park isn’t just about seeing Cloud Gate, there are plenty of things to do to make it a day out. In winter, enjoy ice skating at the McCormick Tribune Ice Rink and in the warmer months, the rink is transformed into a rock-climbing wall.
While at Millennium Park, you can’t miss the magnificent Crown Fountain and its two 50-foot glass towers bordering the reflecting pool. The Crown Fountain towers showcase video projections of Chicago faces and life. You’ll also find rotating public art installations in the park.
Keep an eye out for two designs by architect Frank Gehry. Jay Pritzker Pavilion is a state-of-the-art outdoor concert venue hosts a variety of music events, including the Grant Park Music Festival, free concerts, and movie screenings in the summer. The BP Pedestrian Bridge is a winding bridge that provides a unique pedestrian route from Millennium Park to Maggie Daley Park and offers great views of the park and the city.
Book this Segway tour – perfect for first-time visitors to Chicago, where you’ll visit Millennium Park, Grand Park, and the famous Buckingham Fountain.
2. Stroll the Chicago Riverwalk
Take a stroll along the Chicago River downtown on the Chicago Riverwalk. The Chicago Riverwalk is a 1.25-mile-long path that runs through downtown Chicago. There are shopping, dining, and museums along the path. Plus, it is easy to catch a boat tour from the Riverwalk to take in the sites in comfort.
Start your day with this Yoga Riverwalk Tour. This Yoga-inspired walking tour combines sightseeing and wellness. Follow your guide along the Chicago River Walk while hearing about its history and famous architecture, all while stretching and doing meditative exercises.
3. Chicago Architecture River Cruises
One of the best things to do in Chicago is to tour the city on the Chicago River. The Chicago Architecture River Cruise, also included with the CityPASS, is one of the top attractions in the city. Chicago, known for its rich architectural history, is home to some of the world’s most iconic buildings and world-famous architects. You can book it in advance here.
4. Chicago River Boat Tour
If the architectural history of downtown Chicago isn’t your thing, you can book a shorter 45-minute boat tour of the Chicago River. This family-friendly boat tour with live commentary along the Chicago River is tailored to entertain the whole family and shorter to keep the kid’s attention.
If you are looking for more things to do in Chicago with kids, the Chicago Children’s Museum is another fun to for the kids. A riverboat tour is a great way to take in the skyline and the city’s architecture while enjoying a pleasant trip through Chicago.
5. SkyDeck Chicago at Willis Tower
To get unparalleled views of the Chicago skyline, suburbs, and Lake Michigan, visit the Skydeck Chicago perched high atop the Willis Tower (formerly known as Sears Tower).
If you’re feeling adventurous, hang over the city on the ledge, a glass enclosure with floor-to-ceiling windows and a transparent floor. You’ll feel like you’re floating 103 floors above it all. Visiting the iconic Willis Tower will teach you about Chicago’s history and architecture.
Make sure to download the Willis Tower Skydeck Chicago Mobile App to show famous Chicago Landmarks. The Skydeck Pass gives you express entry to The Ledge, Free Wifi, and Theater presentation.
6. Art Institute of Chicago
In the center of Grant Park, on the famous Michigan Avenue, The Art Institute of Chicago is an architectural masterpiece is easily accessible with the Chicago CityPASS. Just walk between the two lion statues and step into a fantastic collection of art worldwide.
The Art Institute of Chicago was voted the #1 Museum in the World by Trip Advisor, and it’s easy to see why when you gaze at masterpieces by Chagall, Matisse, and Georgia O’Keefe. Located in the Loop community of Chicago’s Central Business District, there are plenty of things to see in this area.
Get your skip-the-line tickets for the Art Institute in advance, where you’ll enter 30 minutes before the museum opens to meet your guide and see iconic pieces by Picasso, Salvador Dali, and Andy Warhol. The Art Institute of Chicago has one of the world’s greatest collections of impressionist art. You can book with peace of mind for a full refund should you cancel within 24 hours of the activity.
7. Take a Chicago Food Tour
A great way to explore Chicago by foot is to book a guided food tour. This guided tour takes you from the Chicago Theater to the Chicago Pedway, where local commuters move about the city’s underground tunnels. You’ll then walk from City Hall to the Chicago Riverwalk, where you’ll see famous landmarks such as the Marina Towers, the Britannica Building, and the Willis Tower.
It’s then on to part two of the Chicago City tour with food tastings in the River North Neighborhood to sample Chicago staples like the Chicago hot dog, popcorn, and Chicago-style deep-dish pizza. Bring your appetite because there’s a lot of food on this tour. Check out more food tours here.
8. Enjoy The Crimes of Chicago Mob and Crime Bus Tour
Chicago has a colorful criminal past with some of the most notorious mob and crime bosses in history. This Chicago crime boss tour is one of the more unique things to do in Chicago.
Ride through the Windy City by bus to see the areas frequented by the likes of Al Capone, John Dillinger, and the Terrible Tommy O’Connor. You’ll see mob staples like the Biograph Theatre, Holy Name Cathedral and the Site of the St. Valentine’s Day Massacres.
This year-round attraction will take you to places like the criminal courthouse where the notorious criminals of Chicago were tried. You’ll recognize names like The Untouchables and Chicago Blackhawks and you’ll see notorious crime scenes from the Windy City like the Biograph Theatre, Holy Name Cathedral, Clark Street Bridge, and the St. Valentine’s Day Massacre
9. The Magnificent Mile
The ‘Mag Mile’ is a mile-long street that boasts over 460 retailers, including restaurants, major department stores, popular brands, luxury labels and designers, as well as three vertical shopping centers, museums, and the Loyola University. It is one of the most popular shopping districts in the city.
This 13-block stretch of North Michigan Avenue is one of the city’s cultural hubs. You can also see historical gems like the Water Tower and Pumping Station, as well as two of the survivors of the 1871 Chicago Fire. Get the full experience complete with lake views by walking the entire mile.
See more of Chicago by booking a tour with ‘Inside Chicago Walking Tours’; they do an incredible job of telling Chicago’s story in an engaging, entertaining way. They’ll tell you some fascinating details about different buildings and areas in the city.
10. TILT At John Hancock Center
Soaring into the Chicago skyline, the John Hancock Center observation deck offers the best views of the city skyline and Lake Michigan.
Don’t miss this landmark of Windy City itinerary. Ascend to the 360 Chicago Observation Deck, and you’re greeted with panoramic vistas that stretch across the city and beyond, offering a bird’s-eye view of Chicago’s stunning urban tapestry and the vastness of Lake Michigan.
But the thrill doesn’t stop there – dare to experience TILT, a unique glass lookout that tilts you over the edge of the building for an adrenaline rush like no other. Beyond its heights, the John Hancock Center is nestled in the heart of the Magnificent Mile, surrounded by a vibrant array of shops, restaurants, and cultural attractions. Its central location makes it the perfect starting point for urban explorers seeking to immerse themselves in the lively spirit of Chicago.
Get a thrill at Tilt, where you get a downward-facing view of the city from 1,030 feet up in the air. Grab a drink at bar 94 and take in the 360-degree views of the skyline and Lake Michigan from its 17,000-square-foot observation deck.
11. Tour the Wrigley Building
The 1920s were an essential time for Chicago architecture, and when the Wrigley Building opened in 1925, it set the pace for the city’s development.
When owner William Wrigley Jr. (of the Wrigley gum company) scouted locations for the building that would become his company’s headquarters, he chose a unique triangle shape of land that eventually became the bustling Magnificent Mile.
This walking tour of the Magnificent Mile takes you on a journey telling the story of how Pine Street turned into the Magnificent Mile – Chicago’s premier shopping district. You’ll see iconic Chicago buildings including the Tribune Tower, the Wrigley Building, and 875 N. Michigan Ave. (formerly the Hancock Tower).
12. Chicago Cultural Centre
If you love Chicago’s stunning architecture, you must visit to the Chicago Cultural Center. This breathtaking building is the home of two magnificent stained-glass domes and stunning rooms showcasing it’s past.
Designed in the Classical Revival style, the dazzling interior has a Tiffany art glass dome, mother-of-pearl mosaics, and a Carrara marble lobby. They offer free exhibitions, music, dance, and theatre events.
13. Navy Pier
Navy Pier is one of the best places to visit in the city. It is a waterfront event space housing year-round attractions. This family-friendly destination has the Pier Park amusement park, where kids can ride the historic carousel, the Wave Swinger or the Centennial Wheel. A 200-foot Ferris wheel that has enclosed climate-controlled gondolas offering beautiful views of downtown Chicago.
This iconic city landmark has welcomed one hundred eighty million visitors in the last 25 years to its 50 acres of attractions and experiences. To get a birds-eye view of the city, jump on the Centennial Wheel, a 200-foot Ferris wheel with enclosed gondolas enabling year round fun for the whole family no matter the weather.
With the Navy Pier Express ticket, you’ll get a fast pass express ticket to ride the Centennial wheel. Located at the Historic Navy Pier, be suspended over Lake Michigan at the mouth of the Chicago River with panoramic views of Downtown Chicago. The Centennial Wheel was built in 2016 to celebrate the 100th anniversary of the Navy Pier opening.
Part 2 – Sports and Entertainment in Chicago
14. Catch a White Sox Game
Baseball is quintessentially American and no trip to a city in the United States would be complete without enjoying a ball game. Something that makes Chicago unique is that it is home to two Major League Baseball teams making baseball a way of life in Chicago. You can’t do Chicago without experiencing a White Sox Game. Guaranteed Rate Field is always filled with enthusiastic fans who cheer on their team while munching hotdogs, burgers and beer. For tickets and game schedule check out the Chicago Whitesox website.
15. Catch a Game at Wrigley Field
Or you can catch the Chicago Cubs play a game at the historic Wrigley Field. Being blessed with two major league baseball teams makes it twice the fun. Wrigley Field is the second-oldest ballpark in the major league. It sits in a residential neighborhood of Chicago close to Lake Michigan and is an excellent way to spend an afternoon or evening in the Windy City.
16. Cheers on the Bulls & Blackhawks at the United Center
Continuing with our sports portion of this list… When in Chicago, a visit to the United Center, an iconic sports and entertainment arena, is a must for any itinerary. Known as the home of the Chicago Bulls and the Chicago Blackhawks, the United Center offers an electrifying glimpse into the city’s sports culture.
Whether you’re catching an adrenaline-pumping basketball or hockey game, or attending one of the many concerts and events hosted here, the experience is always unforgettable.
Don’t miss the famous statue of Michael Jordan, a symbol of the Bulls’ legendary NBA legacy, perfect for a memorable photo opportunity.
17. The Second City
Chicago is famous for its comedy scene and this legendary comedy club launched the careers of Bill Murray, Eugene Levy, John Belushi and Catherine O’Hara and so many more great comedians of our time. Located in the Lincoln Park neighborhood of Chicago, this is one of the top rated things to do in Chicago.
The Second City in Chicago is the original comedy club, but there are Second City’s in Toronto and Hollywood. It was the inspiration for Saturday Night Live and you name a comedian, chances are they worked on their comedy chops here.
18. Chicago Magic Lounge
From a converted 1940s commercial laundry grew the Chicago Magic Lounge, a 7,200 square-foot, art deco-style, theatre, and lounge. It features a 1930s-style speakeasy performance bar, a 120-seat cabaret theatre and a formal close-up gallery named The 654 Club.
Every polished inch of this elegant new nightclub is dedicated to the art of “Chicago-Style Magic”. Don’t miss this Lounge, it’s highly entertaining, full of tasty tid-bits, delicious cocktails, amazing sleight-of-hand, and a whole lot of fun.
One of our favorite things to do in any city is to take a walking tour with a local guide. Chicago is a foodie city and this walking tour lets you discover the best of Chicago as you tour the city’s vibrant food scene. You’ll see the Chicago Theatre made famous in the musical Chicago, where you’ll enjoy food as you learn of the city’s history. Sample everything from the Chicago-style hot dog, Chicago-style deep dish pizzas, popcorn and a classic Chicago sandwich.
Part 3 – The Best Chicago Museums
19. Museum of Science and Industry
Located in the Hyde Park area of Chicago in the former Palace of Fine Arts from the 1893 World’s Columbian Exposition, the Museum of Science and Industry is the largest of its kind in the Western Hemisphere. See a World War II German submarine that was captured during World War II, walk through a replica of a coal mine and run on a human sized hamster wheel.
One of the coolest new exhibits in the Museum of Art and Industry is the 100 Lego sculptures created by artist Nathan?Sawaya. See recreations of masterpieces such as The Mona Lisa, Michaelangelo’s, David, and a giant dinosaur made out of Lego.
20. Museum of Contemporary Art
The Museum of Contemporary Art is a must-stop on your visit and is filled with interactive exhibits, performances, and programs. The MCA is one of the world’s largest art museums, housing over 2,000 works. They take pride in featuring new and experimental work in all types of media.
Over the summer Virgil Alboh’s “Figures of Speech” exhibit drew thousands of visitors who viewed this gender-bending artist/designer’s work. In fact, the exhibit was extended a few more weeks in September 2019, so audiences could take in the Chicago native’s work.
21. Field Museum of Natural History
Families always love a Natural History Museum, and the Field Museum of Natural History in Chicago has everything from an Egyptian tomb to dinosaur exhibits. Opened in 1894, the field museum showcases exhibits dating back 4.6 billion years.
It was named after benefactor Marshall Field, who donated $1 million to turn the collection into a permanent museum. From China to Ancient Egypt, you’ll trace the history of the world. The star attraction is the most complete T-Rex fossil ever discovered.
22. National Museum of Mexican Art
Another unique museum to visit in Chicago is the National Museum of Mexican Art. Celebrated for its colorful and insightful representation of Mexican and Latino art and culture, this museum is located in the lively neighborhood of Pilsen.
Travel is all about diving deep into the essence of a place, and the National Museum of Mexican Art embodies this perfectly. As you wander through its galleries, you’ll be captivated by an astonishing array of artworks, from ancient artifacts to contemporary masterpieces, each telling a story that bridges borders and generations.
This museum is a vibrant celebration of diversity, identity, and the rich tapestry of Mexican heritage. And the best part? Admission is free, making it an accessible cultural gem for all visitors.
Part 4 Parks and Outdoors in Chicago
23. Lincoln Park
Lincoln Park is one of the best places in Chicago to enjoy the great outdoors. There are many things to do from perusing the exotic flowers and plants of the Lincoln Park Conservatory to seeing the animals and flamingoes of the Lincoln Park Zoo and walking along the Lakefront Trail. You can really spend an entire day in just this one neighborhood.
This expansive park and neighborhood houses the Peggy Notebaert Nature Museum and the Chicago History Museum and the Armitage and Halsted is one of the popular shopping districts in the city with plenty of shops and boutiques.
The Lincoln Park Zoo is said to have hauntings in its bathroom, and you can visit it by taking the Lincoln Park Ghost Tour. The bathroom mirror at Lincoln Park Zoo is said to be home to the ghost of the Woman in White. Visit eight historic sites, including the forgotten burial ground, and learn about the gangsters of Chicago and the spirit that haunted Al Capone.
24. Garfield Park Conservatory
Garfield Park Conservatory is one of the most extensive gardens under glass in the world. What makes it even more of a feat is that it was built in 1908. It is often referred to as “landscape art under glass”
Inside, it feels like a tropical rainforest with palm trees and ferns sprawling across 10 acres of gardens and ponds both indoors and out.
25. Chicago Botanic Garden
Discover a serene oasis amidst the bustling city at the Chicago Botanic Garden. This sprawling garden, located just north of Chicago, offers an idyllic escape with its 385 acres of lush landscapes and over 2.7 million plants.
Each of the 27 gardens and four natural areas tells a unique story, offering endless opportunities to immerse yourself in the wonders of nature. Stroll through the Japanese Garden for a moment of Zen, or marvel at the vibrant colors in the English Walled Garden.
Seasonal events like the Orchid Show and the Butterflies & Blooms exhibition add an extra layer of enchantment. For photography enthusiasts, nature lovers, or those simply seeking a tranquil retreat, the Chicago Botanic Garden is a picturesque paradise.
26. Ping Tom Memorial Park
Ping Tom Memorial Park is a hidden gem in Chicago’s bustling Chinatown neighborhood. It is easily accessible by the CTA Red Line or Water Taxi; this park offers a delightful escape with its stunning views of the Chicago skyline and the South Branch of the Chicago River.
The park’s design was inspired by traditional Chinese landscapes. Embrace the spirit of adventure as you kayak along the river or take a stroll through the pagoda-style pavilions and a bamboo garden, providing a tranquil backdrop for meditation.
The playground and fieldhouse offer fun for families, while nearby Chinatown provides a journey into a vibrant cultural and culinary scene.
27. North Avenue Beach
North Avenue Beach is a gem along the waterfront of Lake Michigan. For anyone seeking a bit of adventure, relaxation, and cultural immersion. This popular beach offers more than just a stretch of sand; it’s a lively urban escape where the city’s energy meets the tranquility of Lake Michigan.
From volleyball and kayaking to simply basking in the sun and enjoying the Chicago skyline. The beach’s centerpiece, the sleek, ocean-liner-inspired beach house, provides amenities and unique photo opportunities.
28. Jackson Park
Located near the Museum of Science and Industry, Jackson Park is also worth a stop when visiting Chicago. This historic park is famed for hosting the 1893 World’s Columbian Exposition. The Statue of The Republic is a must-see for history buffs.
Wander through the serene Japanese Garden, a symbol of peace and friendship between Japan and the United States, and immerse yourself in its tranquil ambiance. There is also golfing, and it’s an excellent place for bird watching and exploring the numerous walking and biking trails.
Jackson Park also boasts beautiful beaches along Lake Michigan, perfect for a relaxing day by the water. And soon you’ll be able to see the Obama Presidential Center. Chicago Architecture Center
29. Chicago Jazz Festival
If you are in Chicago in late summer, don’t miss the Chicago Jass Festival. Groove to the soulful rhythms for this annual celebration of jazz. Typically held around Labor Day weekend, this festival transforms Millennium Park into a lively music and culture hub.
As you wander through the stunning Jay Pritzker Pavilion and the surrounding lush gardens, you’re enveloped in the sounds of legendary jazz icons and rising stars, showcasing the diverse tapestry of jazz music.
The backdrop of Chicago’s skyline adds to the magic, making it a picturesque setting for enjoying some of the best jazz the world has to offer. Free to the public, this festival aligns perfectly with ThePlanetD’s ethos of accessible and enriching travel experiences. Whether you’re a jazz fan or a casual listener, the Chicago Jazz Festival is a must-visit event,
Where to Eat in Chicago
Whether you crave street food or fine dining, there are many Chicago restaurants to choose from. Don’t miss the world-famous Chicago Red Hot or a Chicago Deep Dish Pizza, like the one I had at Lou Malnati’s. Check out where to eat in Chicago by local writer Lisa Lubin.
Purple Pig
How could you go wrong with a restaurant having a tagline like ‘Cheese, Swine and Wine’ – all our favorite things! Located in Downtown Chicago, the Purple Pig is my choice for the best things to do in the city.
Try the charcuterie board or Ham Croquettes, Salt-Roasted Beets with Whipped Goat Cheese + Pistachio Butter, Lamb Ribs Harissa BBQ, Lime Yogurt + Fregola, Pork Belly + Tenderloin Ginger Glaze, Carrot + Espresso. No matter what you order it’ll be extremely well-curated.
Lou Mitchell’s
The skillet eggs, hot coffee, and heaping stacks of pancakes have been a staple of this historical diner since 1923. Specializing in breakfast, lunch, and brunch, this Chicago staple is not to be missed. Plus kids will love the free Milk Duds, and adults will enjoy their delicious donut holes.
Michael Jordan’s Steak House
If you love steak then this is the place to be. Located in the InterContinental Hotel it features an extensive wine list. Steak choices come in Slagel Farms NY Strip, New York Strip, Fillet Mignon and an Aged Porterhouse. The menu has an exhaustive list of starters and sides but save room for the signature 23 layer chocolate cake.
Rooftop Bars
In case you haven’t noticed, Chicago also has a happening bar scene where craft cocktails are all the rage. In a city as amazing as Chicago, you should enjoy your drink at a rooftop bar with a view of the Chicago skyline.
- Suggested rooftop bars for great views of the city include:
- Try LH on 21 at London House
- Cindy’s Rooftop at Chicago Athletic Association Hotel
- The Raised Bar, Chicago.
Lou Malnati’s
Never leave Chicago without trying at least one deep-dish pizza, a Chicago staple for as long as one can remember. Lou Malnatti’s does deep-dish pizzas very well. Start with a delicious green goat cheese salad and finish with your selected pizza. Wash it all down with house made Iced tea – they have gluten-free pizza as well.
Portillo’s Hot Dogs
Portillo’s has been around since the early ’60s and it’s the best place to try one of Chicago’s famous hot dogs. Enjoy it any way you like with chili, hot peppers or just plain. Don’t like the “dog” then there’s salads, pasta, and chicken on the menu as well. The lineups at Portillo’s is long at lunchtime but they do move fast.
Where I Stayed in Chicago
Wondering what hotel complements your stay in Chicago? In one of the most prime locations in the city, the InterContinental Chicago is a destination on its own with a door on the Magnificent Mile. Walking into the InterContinental Chicago, you step back in time – to old Chicago with all its glitz and glamour.
The Intercontinental Chicago has one of the best views of Chicago. Enjoy breathtaking views from the Tower Lounge on the 32-floor; a steak in the sophisticated atmosphere of Michael Jordan’s Steak House. Or visit the master sommelier who creates wine tastings paired with perfect treats at Eno Wine Room.
While there, enjoy the 1920s-era pool or a relaxing massage at the spa. The InterContinental is centrally located to everything the Magnificent Mile has to offer – from shops to dining and all the attractions. See more reviews of Chicago on TripAdvisor / Booking.com
Getting Around the City of Chicago
The fastest and most efficient way to get around Chicago is using the L-Train. The elevated train system also operates out to O’Hare International Airport.
You can also get around Chicago from May to Oct/Nov (depending on weather) via water taxi. Uber operates in Chicago.
Another way we love to get around when visiting a city for the first time is to book a hop on hop off bus tour. It let’s you see all the city highlights with one affordable bundle. This double-decker bus goes by the Willis Tower, Wrigley Building, the Shedd Aquarium and Field Museum as well as driving down the Magnificent Mile. You’ll also travel across the Michigan Avenue Bridge over the Chicago River connecting the north and south sides of Chicago.
Purchase 24 or 46 hour tickets and hop on or off as you choose to see the top tourist attractions in Chicago.
As you can see, there are so many amazing things to do in Chicago and we’ve barely scratched the surface. But if you are planning a trip to the Windy City, this guide is a great start for first-time visitors to see the best that Chicago has to offer.
With its world-class museums, historic architecture of the city center, art exhibitions and lively nightlife, visiting Chicago is up there with a trip to New York or Paris. It is one of the greatest cities on earth with many attractions within walking distance of one another. So what are you waiting for? Book your trip to Chicago today.
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