Last Updated on March 18, 2023

Imagine driving an interstate highway on a clear day as your eyes turn towards two giant toothpick-like antennae in the sky. Willis Tower is among the top Chicago attractions for tourists. As you journey on further, keeping your eyes on those antennae, get ready for the rapid budding of Chicago’s towering skyscrapers on the horizon.

If you are flying in from either O’Hare or Midway International Airports, regard the iconic Chicago skyline from the air with long narrow strips of golden, sandy beaches constantly being swept by the rolling waves of Lake Michigan.

Found on the second-largest Great Lake by volume and third by surface area (just slightly smaller than West Virginia), the Windy City welcomes you. 

With a population of 2.7 million citizens in an area of 11,841 square miles, Chicago is the third-largest city in the United States. It has been called many names such as City of Broad Shoulders, Chi-town, Windy City, Mud City, Second City, and the Heart of America. Chicagoans, as we like to be called, are welcoming, friendly, and proud to stand behind all of these aliases.

Whether you stop us on the street to ask for directions, talk to us about our successful (or not-so-successful at the time) sports teams, or order a classic Red Hot from a Chicago-style hot dog street vendor (more to come on this later), you will be awarded a smile and get to hear our “short a” vowel sound accent. 

In that spirit, here, advice from a local: Chicago attractions for tourists.

What to see in Chicago, IL

Take the Family and Friends to Navy Pier

You can spend an entire day exploring the 3,300-foot-long pier off of Lake Michigan. The most picturesque views are revealed riding the two-sided gondolas of the spectacular state-of-the-art Ferris wheel, the Centennial Wheel. For more aerial adventures, be rushed to the top only to drop way down low on the Light Tower, or fly through the sky on the Pepsi Wave Swinger.  

If heights aren’t your thing, ride the classic carousel. Or let the kids be kids at the Children’s Museum; it’s full of fun activities for young ages. Or try the 4,000-square-foot Funhouse Maze for fun for the whole family.  

Afterward, relax with a cold brew at the Beer Garden while listening to a live band, and observe the frolicking lake activity of the boaters with the backdrop of the skyline. 

Navy Pier is also one of the best viewpoints for the annual summer Chicago Air and Water Show. This two-day event started back in 1959 and has drawn millions to thrilling exhibitions and demonstrations of pilots, parachute teams, and diving teams performing stunts both on roaring aircraft overhead and buzzing boats in the lake.

If you would rather be part of the water activities, purchase a ticket for a beautiful sunset dinner cruise or a thrilling speedboat tour. Rent a pontoon boat and join the local boaters at the Playpen, a hangout pocket of the lake for socializing. Kayaks, paddleboards, canoes, motorboats, and even yachts are available to rent from Monroe Harbor or Chicago Riverwalk.

For indoor fun, stroll through the mall of souvenir shops and kiosks; explore the lush green Crystal Gardens under a six-story greenhouse filled with palm trees, exotic flowers, and a dancing fountain; or immerse yourself in a 3D IMAX experience with luxury seating, golden butter-drenched popcorn, and the latest blockbuster movie. 

Bring Your Appetite 

When it comes to food, deep dish pizza is the iconic must-have indulgence for visitors. We take the term pizza “pie” literally and bake our pizza in an iron skillet or pie pan allowing for a deep bowl-like crust that is filled with an upside-down technique of thick layers of crushed tomatoes, your choice of favorite toppings, and finished with a blanket of milky mozzarella cheese.

When it is brought to your table, the server expertly serves each piece using an actual pie knife. Your choices are deep dish, pan, or thin crust. 

The most popular pizzerias are Lou Malnati’s, Pizzeria Uno, Pizzeria Due, Giordano’s, Pizano’s, Flo and Santo’s, and Gino’s East. The list could keep on going. For the best bang for your buck, take one of the many Chicago pizza tours to sample it all. You can book either walking or bus tours at chicagopizzatours.com or pizzacityusa.com

You’ll notice hole-in-the-wall storefronts with brightly colored signs, neon lights, and/or a drawing of hot dog in a bun with names like Superdawg, Wolfy’s, Jimmy’s, and Booby’s. What’s so special about a hot dog you ask? A Chicago Red Hot is a steamed poppy seed bun enveloping a “red” all-beef frankfurter bookended with finely chopped white onions, florescent green sweet relish, daisy yellow mustard, firm tomato wedges, and topped with a dill pickle spear, tart spicy sports peppers, and a sprinkle of celery salt.

Would you like a side of cheese fries and a cold pop (soda) with your order? Yes, please!

Other popular Chicago-style fast foods are Italian beef (dipped or dry), Italian sausage with red gravy, fried pizza puff, and the gyro. To eat like a local, add giardiniera (pickled peppers, olives, cauliflower, celery, and carrots) for a spicy kick.

Chicago’s diversity is displayed in a multitude of ethnic restaurants. The city is a foodie mecca of authentic cuisines from around the world including Armenian, Georgian, Malaysian, Phillipino, Senegalese, and the always favorite home-cooked Italian.

Within these cozy mom-and-pop cafes and Michelin-star restaurants the culinary world is open to all in Chicago.

If you are looking for variety under one roof, Chicago food halls have become the trendiest spots for work lunches, happy hours, and weekend dinners with friends. It’s a great option for sampling a variety of cravings from specialty vendors and does well for groups with various diet preferences and restrictions. 

Experience the Mix of Cultures

The immigration of various cultures to the city developed the 77 neighborhoods with a distinct personality from individual history, special events, shops, and culinary treasures. 

Summers bring neighborhood festivals. Some are ethnic-based, such as Ukrainian Days Fest in the Ukrainian Village neighborhood where everyone is welcomed to learn about the heritage through the universal languages of music, food, and drinks. While others such as Taste of Lincoln Ave boast public block parties with food booths set up by neighborhood restaurants selling their popular dishes and family-friendly entertainers and bands to liven up the crowd. 

You don’t have to wait for a holiday or special event to enjoy the city’s diversity and cultures as restaurants, grocery stores, bakeries, and specialty shops of traditional garments, trinkets, and goods are woven into these neighborhoods. Little Italy, Chinatown, Little India on Devon Ave, the Jewish neighborhood of West Rogers Park, and the Mexican-American neighborhood of Pilsen are just a few examples.

Take A Ride

You won’t need a car if you are staying in or near the city as getting around is very easy with rideshares and taxis. However, for the true city experience use the CTA (Chicago Transit Authority) subway train system we call the L.  

This quintessential mode of transportation has been representative of Chicago in movies and television for good reason. It’s the most rapid form of transit and most effective in avoiding traffic congestion. Tracks run both under and over the city streets.

If you are staying in the surrounding suburbs that we call Chicagoland, there are Metra commuter trains that connect to the L to take you into and out of the city.  

Here’s one travel tip: pick up a Ventra Card from any L station. Fare values and passes can be loaded at the station, online, or on the Ventra app.  

You will notice numerous bike racks with rows of blue aluminum-framed bikes with the word “Divvy” painted on them. This biking sharing system, operated by Lyft, has revolutionized how Chicagoans and tourists move about the city in an environmentally friendly way (weather permitting of course). For more information, visit divvybikes.com.  

For the safety of all bikers, designated bike lanes have been marked on the streets of downtown and major, high-traffic neighborhoods. For a more scenic ride, rent a bike to ride on the scenic Lakefront Trail. This is a 19-mile asphalt and concrete stretch along the shore of the lake and downtown with many of the aforementioned touchpoints for pit stops along the way.  

Another popular scenic trail is “The 606” Bloomingdale trail that was once the blue line for the L. It was carved into a biking and walking trail to connect the east and west sides as well as expand the city’s green space for Chicagoans to enjoy.

Stroll The Museums

The Art Institute of Chicago. Michigan Avenue Entrance.
The Art Institute of Chicago. Michigan Avenue Entrance. Courtesy of the Art Institute of Chicago.

With 50-plus museums, a selection of them have to be on any list of Chicago attractions for tourists. Catering to a multitude of interests from contemporary art, maritime history, sports, and money to life underwater, on another planet, or millions of years ago, surely you will find one to interest you. Five of the most popular museums are located downtown nearby each other.

At the Museum Campus, located on Lake Shore Drive and Roosevelt Road, check out the 32,000 aquatic animals (1500 species) inhabiting five million gallons of tank volume at the Shedd Aquarium.

Across the street at the Field Museum you and your family will be greeted by Sue, the oldest, largest, and most complete Tyrannosaurus rex.

Next door is Doane Observatory and the Adler Planetarium, home to the largest publically accessible aperture telescope. View celestial objects in our universe that are trillions of miles away.  

Another travel tip: take advantage of the Go Chicago pass and visit all three attractions and more at gocity.com.

Just north of the campus, on Lake Shore Drive, take a left on Monroe Street and walk two blocks to savor the expansive collection of famous paintings at the Art Institute of Chicago, one of the world’s great art museums. 

10 minutes’ drive south on Lake Shore Drive at East 57th Street, the Museum of Science and Industry is a favorite for science nerds and transportation experts who love planes, trains, and automobiles. You can venture through a U-505 German Submarine captured during World War II or weave through the tunnels of a giant model of the human heart. During the holiday season, families and school trips bring children to admire the whimsical decorations of over 50 Christmas trees from around the world. Find out more at msichicago.org

Appreciate the Art

Downtown Chicago is rich with glamourous architecture and unique artwork as evidenced by the preservation of its historical structures and welcoming of new artists in open public spaces. While soaring skyscrapers of all shapes, sizes, and colors are all around you, the recommended way to learn about their origins and designers is to take one of the many city tours. 

On land, walking tours and double-decker bus tours are a sure way to experience the city highlights and learn of the architects and engineers involved in creating our grand skyline.

There is also the option of taking a scenic architectural river cruise down the Chicago River that showcases iconic buildings such as the Willis Tower, John Hancock Center, Aqua Tower, and more. Architecture is one of the top Chicago attractions for tourists… you’ve seen “The Break-Up,” haven’t you, where Vince Vaughn plays a Chicago architecture tour guide on the river?

You will find the local guides to be very passionate and knowledgeable as well as eager to entertain you with interesting stories of the city’s grandeur. Be sure to ask about the juicy history and rumors of the Crain Communications Building, also known as the Diamond Building. 

One of the city’s most infamous events was the Great Chicago Fire in October 1871. Rumored to have been initiated by Mrs. O’Leary’s cow kicking over an oil lantern and igniting fires, the blaze was then carried by hot, dry winds to the wooden construction and set the city ablaze for miles. Reconstruction afterward was led by new building styles such as the steel-framed skyscraper.  

Up until 1998, Sears Tower, now named Willis Tower, was the tallest building in the world. Today, though no longer the tallest, it still holds the record for highest roof deck, elevator ride, and inhabitable floor. A trip to this Chicago icon would be incomplete without visiting the Skydeck on the 103rd floor and stepping out onto the all-glass ledge. View the city at your feet, literally! 

The 96th floor of the John Hancock Center also has a 360-degree view of shimmering city night lights. Enjoy a drink at the grand bar or dine at the restaurant just one floor below. 

The city pays tribute to countless world-famous artists. You can find them in parks, the city center, courtyards, or around the corner on the sidewalk. 

The south end of Millennium Park opens to the Lurie Garden, a grand city park of vivid wildflowers among lush prairie plants of the Midwest. Here you will find a showcasing of modern art called Cloudgate by Indian-born British artist Sir Anish Kapoor. We affectionately refer to this giant silver structure as the Bean. With some trial angling and positioning, you can take a picture of your reflection with the swirling contour of the Chicago skyline behind you as a backdrop.

Families can also splash and play at Millennium Park’s two-towered interactive video sculpture, the Crown Fountain, by Spanish artist Jaume Plensa. 

In the center of Grant Park, the French-inspired Buckingham Fountain was designed by architect Edward H. Bennet. It’s shaped like a wedding cake and decorated with statues by French sculptor Marcel F. Loyau. From spring to fall, the fountain dazzles crowds with hourly water shows of lights and music. 

While at Grant Park, visit the south end so you don’t miss the iron sculptures of 106 headless (and armless) giants of Agora. The statues were designed by Polish artist Magdalena Abakanowicz. 

The Richard Daley Center is another great central location to visit; inside there is an untitled Picasso sculpture that puzzles and inspires both tourists and locals alike. Kitty-corner to the Daley Center stands Jean Duffet’s fiberglass sculpture, Monument with Standing Beast. (Chicagoans will refer to it as Snoopy in a Blender.) And Alexander Calder’s Flamingo is less than four blocks south on Dearborn Street. 

Reserve Tickets to a Show

The Chicago Theater District, again, a classic of Chicago attractions for tourists, is a vibrant and lively locale in the Loop. Here you can reserve seats to big-time Broadway shows, award-winning productions, and world premieres as well as indulge in the classics at any of the districts’ popular theaters including Cadillac Palace Theatre, CIBC Theatre, James M. Nederlander Theatre, Chicago Theatre, and the Goodman Theatre. For ballet lovers, the Joffrey Ballet performs at the Auditorium Theatre just south of the district. For Shakespearean enthusiasts, the Chicago Shakespeare Theater at Navy Pier has the classics.

For new and upcoming talent, Chicago is sprinkled with independent theaters such as the Steppenwolf Theatre known for projecting the careers of actors Joan Allen, John Malkovich, and Gary Sinise. 

“A day without laughter is a day wasted,” said Charlie Chaplin.

Don’t waste a day without checking out an improv show at the infamous Second City comedy theater where legends of comedy such as Bill Murray, John Candy, Mike Meyers, Dan Aykroyd, and Catherine O’Hara debuted. 

Chicago is also known for what we call storefront theaters. These can be unique theater companies who have either boldly transformed a storefront space to make a permanent home for small audience shows or traveling companies that set up shop in various venues across the city. Add your name on their mailing lists to see where they will pop up next.  

Catch a Game

Are you a sports fan? If you answered yes, then you came to the right city! We love our sports teams and love discussing them more, no matter the season or their win record.  

Our baseball season is open at two ballparks, delineated by locals as the Northside and Southside teams. Wrigley Field, home of the Chicago Cubs (northside), is one of the few antique baseball parks still in use in the United States with a manually-operated scoreboard, ivy-covered outfield walls, and an organist. Other baseball fans bleed black and white for the southside Chicago White Sox, who play at Guaranteed Rate Field (formerly Comiskey Park and US Cellular Field). Renovations were completed in 2019 with a Rain Room to cool off during the dog days of summer and a 15,000-square-foot Kids Zone to keep little ones entertained.

Chicago is also a football town as it cheers for the Monsters of Midway at Soldier Field, the oldest stadium in the NFL. Even on a frigid, wintry game day, you can find face- and body-painted fans loudly chanting “Da’ Bears” while tailgating throughout the South Loop.

For Major League Soccer fans (the other football), the Chicago Fire has announced that they will be blazing down the natural grass field at Soldier Field starting this year.    

See the flying statue of Chicago’s all-time legend and basketball hero, Michael Jordan, who led the Chicago Bulls in winning two, three-peats in the 1990s. The nostalgia for those times runs high and the games are still revered: when you enter the arena look up at the six championship title banners proudly hung from the rafters. 

The United Center is also home to our six-time Stanley Cup title ice hockey team, the Chicago Blackhawks.  

Hear the Music

Music is a must when visiting the birthplace of soulful Chicago blues. This urban version includes electric guitar and harmonica with some tunes including drums, bass, and piano. Infamous blues clubs such as Blue Chicago and Kingston Mines are casual and friendly venues known as rustic gardens for growing authentic talent of the down-and-dirty blues.  

Jazz music has a special place in the hearts of the people of Chicago and has long been enjoyed at snazzy bars such as the Jazz Showcase and Andy’s Jazz Club. 

Meet fellow classical music lovers at events throughout Chicagoland at musical theaters such as the Chicago Symphony Orchestra, Civic Opera House, and Harris Theatre.  

Chicago is also the home to one of the biggest music festivals in the United States, Lollapalooza, where more than 170 global bands come together on eight stages for a four-day concert series in Grant Park. Musicians from genres including punk and alternative rock, pop, heavy metal, hip-hop, and more have collided for music lovers since this once world-touring extravaganza planted permanent roots in Chicago in 2010. 

Lollapalooza is not the only music festival drawing toe-tapping, hand-waving, sing-along crowds. Other annual summer outdoor concerts include Ravinia, Blues Festival, Jazz Festival, Taste of Chicago, Pitchfork Music Festival, Riot Fest, World Music Festival, RuidoFest, Reggae Festival, Maritime Festival, Chicago Open Air, Grant Park Music Festival, North Coast Music Festival, Spring Awakening, and Summer Dance. 

Listening to live music, on of best Chicago attractions for tourists.

Celebrate the Winter Holidays

The winter holiday season opens with the Chicago Thanksgiving Day Parade on State Street in the city’s Loop with a lively marching band, a giant inflatable Turkey, and entertaining floats. 

To shed off some of that Thanksgiving meal guilty calories join the Hot Chocolate 15K run or any of the neighborhood Turkey Trots throughout the city.

Chicago will be brimming with the holiday spirit as approximately one million festive lights glow on 200 trees as part of the Magnificent Mile Lights Festival. The charmingly decorated windows of a city landmark, Marshall Field’s (now Macy’s), are a trademark tradition with new themes each year. There is no better way to enjoy the decor than by nestling under a blanket with your loved ones on a horse carriage ride through downtown.

Grab a paper cone filled with warm cinnamon-and-sugar-roasted nuts or a bucket of cheddar and caramel popcorn from local street vendors or snack shops such as Nuts on Clark and Garrett’s Popcorn Shops for your city stroll or carriage ride.

The Friday before Thanksgiving marks the opening day for over 1,000,000 Chicagoans and tourists to attend the most anticipated holiday market in the midwest, the enchanting Christkindhl Chicago Market. Here you can shop the quaint market for handmade ornaments and decorations from Germany, Ukraine, and Austria, drink rich hot cocoa and spiced wine, and indulge in sweet and savory snacks all while listening to a holiday brass band or caroling choir. 

Celebrating Hannukah? The Center for Jewish Life and Chabad of Lincoln Park hosts a gorgeous Grand Menorah Lighting in Daley Plaza. Chitribe.org is a great resource for Jewish events such as dreidel tournaments, trivia nights, and socials sponsored by restaurants and centers to gather the youth for fun drinks, sweet doughnuts, and traditional latkes.

Chicago celebrates Kwanzaa from December 26th to January 1st at venues such as the DuSable Museum, the Bronzeville Children’s Museum, and the Rootwork Gallery. A week filled with hearty feasts, meetings with friends and family, and gift sharing with loved ones while celebrating the seven core principles of this beautiful African-heritage holiday.

Bring in the New Year with a reservation at any of the numerous restaurants throughout the city. You will find both kid-friendly and adults-only New Year’s Eve dinner packages that suit your group. For the party-goers, tickets to New Year’s Eve balls at the fabulous Congress Plaza Hotel or the Crystal Ballroom at Navy Pier sell out fast! Another festive option is to head down to the lakefront or anywhere along the riverwalk to catch the countdown and fireworks displays. 

Shop the Magnificent Mile

New York has 5th Avenue. Los Angeles has Rodeo Drive. In Chicago, we have the Magnificent Mile. True to its namesake, this magnificent 13-block span of Michigan Avenue is brimming with high-end shops, premium fashion outlets, charming boutiques, luxury hotels, and trendy restaurants.  

This robustly popular shopping area in Chicago boasts more than 450 retailers including individual chic designer brands such as Tory Burch, Burberry, Louis Vuitton, and Ugg as well as large department store retailers such as Nordstrom, Saks Fifth Avenue, Neiman Marcus, and Bloomingdale’s.  

Specialty shops such as Sephora, Lush, and Mac may lure you in with their colorful window displays showing off their seasonal cosmetic collections. Or find the perfect piece of fine jewelry at Cartier, Tiffany and Co., and David Yurman. 

For the more active visitor, there is no shortage of popular sports and outdoor brand shops such as Nike, Under Armour, and Patagonia. Kids’ stores such as the Disney Store, the LEGO Store, and American Doll Place carry their latest and most exclusive merchandise as well. 

You can do all of your shopping in one place at any of the three multi-story shopping malls on this grand boulevard: 900 North Michigan Shops, the Shops at North Bridge, and Water Tower Place. 

Enjoy a Night Out On the Town 

The notorious Al Capone was once a big name on the streets of Chicago. The American gangster had command of over 10,000 speakeasies within the city during the Prohibition era. Today these secret bars serve up the trendiest cocktails under dimly-lit, wood-paneled ceilings. Low, cool jazz music playing in the background makes for an intimate outing.

For a more holistic experience, learn the history, hear the stories, meet the bartenders, and savor the drinks by checking out the vibes on a Chicago Prohibition Tour. For more information visit prohibitiontours.com.  

Rooftop bars in the summer and soaring hotel lounge bars are staple hangouts for evening and weekend socializing with friends. 

For those who prefer feet on the ground and fraternizing with locals, you will want to visit any of the hundreds of neighborhood bars, wine bars, and sports bars sprinkled throughout the city’s most popular neighborhoods. 

Finding a spot to get your groove on in Chicago is easy as there is no shortage of nightclubs. Options range from lively venues with jazz, country, rock, salsa, and Chicago blues bands to glitzy dance clubs with DJ masters of top 40 hits and electronic music.

Chicago welcomes 58 million domestic and international visitors per year, making this the second most visited city in the United States. There are countless neighborhoods, activities, and culinary adventures for you to explore during your visit.

No matter what time of the year you decide to visit, Chicago welcomes you with big-city exhilaration, neighborhood warmth, and the cool natural breeze from the shores of Lake Michigan. And now you have a few more must-dos to add to your itinerary! As Frank Sinatra sang, “Chicago, Chicago that toddling town…” 

Author

  • Shraddha Majcher

    As a Chicago-born Indian woman aspiring to the world of travel writing, I cherish discovering traditions related to wellness, foods, customs and celebrations. As a first-generation American growing up in two cultures, I have much perspective to share. Coming from the world of healthcare, with opportunities to travel with wellness in mind and surround myself with beauty, I am inspired to capture enlightening stories in my journey as my contribution to spreading love, good health and cultural respect.