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City Guide: Chicago - How to visit the Windy City

September 9, 2021 By Deborah Wakefield

Like Goldilocks in the classic nursery tale, I've looked high and low and found Chicago to be my "just right" American city. Much as I love New York, my sensible shoes and dutiful observance of flashing "Don't Walk" signs immediately flag me as a tourist in a sea of fashionable jaywalkers on their way to the latest, coolest restaurant/gallery/club. And my chubby 5'2" frame screams "outsider" in casual-glam LA, where super-fit residents sip designer cocktails and nibble on cauliflower-crust pizzas topped with charred kale.

You can keep the kale. I'll take Chicago, where the pizzas are deep-dish, the vibe is down-to-earth, and the music a heady jazz-blues mix.


Chicago is a big city with dozens of distinct neighborhoods and a well-earned reputation for architectural diversity. First-time visitors often stick to the better-known areas—The Magnificent Mile (shopping on steroids), Lincoln Park (a nature lover's paradise), South Loop (home to Museum Campus), and Hyde Park (home to former President Barack Obama). For those who want to venture a bit farther off the usual visitor track, however, check out Choose Chicago's fantastic Neighborhood Guide. It provides a great overview of more than 40 neighborhoods, including tips on things to see, places to eat and where to stay.

Free Tours: You can book free guided tours of Chicago's neighborhoods with a Chicago Greeter tour. These 2-to-4-hour explorations are led by friendly locals, who offer a deep dive into the personality and history of each district. Tours can be customized based on your choice of neighborhood, language and interests.

Neighborhood: The Loop (downtown)

The Travel Channel's inventory of the world's most incredible architectural destinations consistently puts the city of Chicago near the top of the list. And the Windy City has embraced that honor. The Chicago Architecture Center (CAC) is located in the Illinois Center at the start of The Magnificent Mile (Michigan Avenue and Wacker Drive), The CAC, which offers architectural walking, bus, train and boat tours, opened its newly refurbished museum in 2018. A favorite exhibit is a massive model of the city of Chicago, located on the center's first floor in an atmospheric, low-light gallery that heightens the drama about to unfold. The model includes more than 4,200 individual buildings and uses dynamic video and lighting effects to visually accent the city's history. It is especially chilling to watch an eerie orange-red glow engulf large swaths of the model to illustrate the devastating path of the Great Chicago Fire of 1871. (Note: In October 2021, Chicago will observe the 150th anniversary of the fire that was the impetus for changing a small city on the prairie into the thriving metropolis it is today.)

Just steps from the CAC is the Chicago Riverwalk, a pedestrian-only walkway that borders the Chicago River. In addition to top-notch people watching, you'll find the dock for the Chicago Architecture Foundation Center River Cruise aboard Chicago's First Lady. In 2021, this internationally renowned sightseeing excursion was named the "Best Boat Tour in North America" on the USA Today 10Best Readers' Choice list. It also has the honor of being the city's "Official Architecture Tour." What makes it a true standout is its people. For more than 25 years, the CAC's expertly trained architecture docents have led the 90-minute river cruises, sharing stories behind 50+ buildings along the Chicago River and pointing out striking architectural details. The tour also travels under several bridges (Chicago has more drawbridges than any other city in North America). Many of these bridges and their bridge houses are prime examples of major architectural styles, including Art Deco, Beaux Arts and Modernism.

Bridge Lifts: Twice yearly—spring and fall—the city coordinates bridge lifts to allow sailboats and other recreational craft to make their annual trip from the open waters of Lake Michigan to their winter moorings. Visitors lucky enough to be in Chicago on scheduled bridge lift days can watch the fascinating choreography of bridges opening and closing in succession during these "boat runs." Check with the Chicago Department of Transportation's website for more information.

Once you've surveyed Chicago's architecture from the water, how about a bird's-eye view? Skydeck Chicago is located on the 103rd floor of Willis Tower, the second tallest building in the Western Hemisphere (New York's One World Trade Center building claimed the No. 1 spot when it opened in 2014). Skydeck offers spectacular views (weather permitting) that span 50 miles (80 km) and up to four states. The Ledge at Skydeck—an enclosed glass balcony extending 4.3 feet (1.3 meters) outside the building—dares visitors to step out for a head-spinning view 1,353 feet (412 meters) straight down.

Skydeck recently completed a multi-year, multimillion-dollar renovation. A highly interactive museum serves as the new Skydeck entrance. Designed for the Instagram generation, the museum has lots of places to take selfies, including a giant deep-dish pizza platform and a 9-foot-long (2.7 meters), Chicago-style (no ketchup!) hot dog bench. Another standout exhibit is the life-sized "L" train car that takes "passengers" on a tour through nine different Chicago neighborhoods. You'll feel the motion of the train through the seats as the windows (actually video screens) display footage of each neighborhood.

In Ferris' Footsteps: Most Gen Xers remember the movie "Ferris Bueller's Day Off," which focused on the Chicago escapades of three truant high-school students: the eponymous Ferris (Matthew Broderick), his girlfriend Sloane (Mia Sara), and Ferris' sad sack best friend Cameron (Alan Ruck). Among their many adventures is a visit to Willis Tower (then known as the Sears Tower), where they press their foreheads against the glass to see the view straight down (this was before the Ledge glass balconies were added). Skydeck's recent remodel added footprints in the carpet to indicate where the actors stood when the iconic scene was filmed.

Another stop for Ferris and his friends was the Art Institute of Chicago, where the film's characters ponder works of art by Mary Cassatt, Pablo Picasso, Jackson Pollock and others. (The late John Hughes, who wrote and directed the film, has said that he regularly took "refuge" at the Art Institute when he was in high school. The paintings featured in his later movie were among his favorites.)

One of TripAdvisor's top-ranked museums in the world, the Art Institute has the greatest Impressionist collection outside Paris. Stand before classics like Water Lilies (Claude Monet), A Sunday at La Grande Jatte—1884 (Georges Seurat), The Poet's Garden (Vincent van Gogh) and Woman at Her Toilette (Berthe Morisot). Beyond the Impressionism galleries, you'll encounter lots of other famous artworks (e.g., American Gothic by Grant Wood), as well as discover groundbreaking work by new artists. There are dozens of other galleries where you can see the art of ancient Greece, Japan, Africa, the Americas and more.

Within a few blocks of the Art Institute is Millennium Park. Here you'll find the sculpture Cloud Gate (aka "The Bean"), one of the most photographed spots in Chicago. Nearby are the Crown Fountain, peaceful Lurie Garden (a free, four-season garden) and the Jay Pritzker Pavilion, used for the Chicago Blues Festival, the Chicago Jazz Festival and other events.

Neighborhood: The Magnificent Mile (downtown shopping district)

In a city that was home to the world's very first modern skyscraper, it shouldn't be surprising that there's a second tower whose observation deck is open to visitors. 360 Chicago lives up to its name, offering panoramic views of the Chicago skyline and Lake Michigan waterfront. 360 Chicago's Tilt experience is a thrilling attraction not for the faint of heart. Once guests are safely positioned on the Tilt platform and holding the handrails (usually with a sweaty, white-knuckled grip), the entire structure tilts outward from the building, giving riders the feeling of falling forward. After you catch your breath, you'll enjoy a view 1,030 feet (314 meters) down to The Magnificent Mile.

Neighborhood: South Loop (Museum Campus)

Bordering Lake Michigan, the South Loop is home to Museum Campus, where three of Chicago's largest attractions are located: Shedd Aquarium, Field Museum and Adler Planetarium.

From whales to snails to angelfish and zebra sharks, meet 32,000 animals from aquatic habitats around the world at Shedd Aquarium. Sharks cruise at a diver's-eye view, stingrays swim below your feet, and beluga whales smile. Definitely make time for Shedd's "4-D Experience," which brings on-screen movies to life with such special effects as water mist, breezes, bubbles, enhanced floor lighting and seat vibrations.

Although the animals are the stars of the show at Shedd, pay attention to the beautiful sea-themed design touches throughout this nearly century-old Beaux Arts building. Personal favorites: The historic clock that uses nautical symbols in place of numbers and the octopus light fixtures (both visible in the main lobby).

Next door to Shedd Aquarium is the Field Museum. Here you can see many of the world's wonders in one place. Come face to face with SUE, the most complete Tyrannosaurus rex skeleton ever discovered. SUE's new home in the Griffin Halls of Evolving Planet is part of a renovation that was completed recently. After peeking in on the dinosaurs, descend into an ancient Egyptian tomb, journey along an evolutionary timeline and explore more than 10,000 years of Chinese history and culture.

Sassy SUE: SUE the T. rex has their very own Twitter account. (Note: Scientists aren't sure if SUE was male or female, so on Twitter, SUE uses "they/them" pronouns). The loquacious theropod keeps followers on their toes with such cheeky pronouncements as "I haven't heard the Olivia Rodrigo album. I'm 67 million years old. I find it hard to relate to songs about getting your driver's license."

America's first planetarium—Adler Planetarium—sits on a small point of land that juts into Lake Michigan. In addition to that stunning wraparound view of the lake, the planetarium houses one of the world's finest collections of antique astronomical instruments, including sundials, astrolabes and telescopes, plus plenty of hands-on exhibits for smaller astronauts.

The planetarium's historic Atwood Sphere is a must-do. Built in 1913 (and fully restored in 1999), the sphere provides a magical experience that holds its own against anything our tech-crazy culture has developed in the last century. Twelve guests sit on seats in a sled-like vehicle that slides up into a large, rotating celestial sphere (a curved ball of galvanized sheet iron perforated with 692 tiny holes that replicate the stars visible to the naked eye in Chicago's sky in 1913). Once the door closes behind the guests, viewers encounter a star-filled sky. As the sphere rotates, familiar constellations appear in the east, while others dip in the west. This celestial display continues until a simulated sun rises and eclipses the stars. Adler Planetarium will fully reopen in March 2022.

Neighborhoods: Streeterville and Lincoln Park (family friendly)

Traveling with kids? Head to Streeterville and Lincoln Park.

Streeterville is where you'll find Navy Pier (named in honor of the Navy personnel based there during World War I) and the Chicago Children's Museum. Navy Pier is packed with family-friendly rides, dining options, summer fireworks and the Crystal Garden, a six‐story glass atrium that holds more than 80 live palm trees, lush foliage, hanging twinkle lights and fountains. The pier's historic carousel, with its 36 hand-painted animals, is great for little kids. Tweens and teens will flip for the Centennial Wheel, which takes riders 200 feet (61 meters) into the air. And don't worry about the season: The Centennial Wheel's enclosed gondolas give riders a comfortable experience year-round.

Navy Pier is one of the two departure points for Shoreline Sightseeing tours, whose fleet of distinctive blue-and-white boats cruise both the Chicago River and Lake Michigan. Spring through autumn, passengers can drink in Chicago's striking skyline—and a little history—on a relaxing, 40-minute Skyline Lake Tour. Or, opt for a Wednesday or Saturday-night cruise and you'll have the best seat in the city for the Navy Pier fireworks display (summer only).

Shoreline Sightseeing's Architecture Tours were named TripAdvisor's #1 Travel Experience in the U.S. in 2020. Expert guides narrate this 75-minute cruise through the heart of the city. It's also one of the best ways to collect photos of some of Chicago's most iconic buildings, including the classic Beaux Arts-style Wrigley Building, built in 1924 by chewing gum mogul William Wrigley Jr.; Marina City (aka "the corncob towers"), a retail-condominium complex that has appeared in so many films (Batman Begins, The Blues Brothers, Ferris Bueller's Day Off, The Break-Up and more) that it should have its own SAG membership; and the Lyric Opera House, an Art Deco beauty that opened just six days after the devastating stock market crash of 1929.

Lincoln Park is home to the aptly named Lincoln Park Zoo, as well as lots of outdoor spaces where you can let the kids burn off their excess energy. In a city where skyscrapers rule, the Lincoln Park Zoo is dedicated to all things wildlife. Although its founding in 1868 makes the zoo the fourth oldest in North America, its practices are decidedly modern. Its creative enrichment programs are designed to simulate natural environments, like the automated belt feeder that distributes 80% of the pygmy hippos' diet in different locations throughout their habitat at unpredictable times. This encourages the animals to forage, just as they would in the wild.

Budget Tip: The Lincoln Park Zoo's conservation efforts extend to your wallet. As one of the few free zoos in the United States, it'll definitely help save your travel budget.

Neighborhood: Hyde Park

Hyde Park is Chicago's idea incubator. This is the birthplace of big ideas, new ideas, deep ideas and even a few crazy ideas (i.e., the world's first artificial nuclear reactor being secretly built in 1942 under the University of Chicago's old football stadium). This intellectually inclined neighborhood is bookended by the University of Chicago to the west and the Museum of Science and Industry to the east. In between are Frank Lloyd Wright's Robie House, a stunning example of Wright's Prairie-style architecture and a UNESCO World Heritage Site; the DuSable Museum, the country's first institution dedicated to African American history; and the much photographed Fountain of Time, where an ominous cloaked Father Time figure presides over a reflecting basin and a wavelike procession of 100 human figures for whom time will eventually run out.

If you need to jumpstart your own creative juices, the Museum of Science and Industry will happily provide the spark—literally. The popular Science Storms exhibit has a 20-foot (6 meters) Tesla Coil that puts on a 1.5-million volt display of electrical discharge. You can observe the show from a reclined bench, oohing and aahing as the charge builds and brilliant arcs of indoor lightning jump 10 feet (3 meters) from the center of the coil to the outer grounding rings. Nearby, a 40-foot (12 meters) tornado—a vortex of swirling, illuminated vapor rising continuously from the floor—is the most mesmerizing of the museum's exhibits.

Long as a city block and three times the weight of the Statue of Liberty, a World War II German submarine is displayed on the museum's lower level. The U-505 exhibit tells the nail-biting tale of the deadly U-boat's capture.

Other museum must-do's include the walk-through Numbers in Nature: A Mirror Maze, whose design mirrors (get it?) the mathematical patterns that abound in nature; the Giant Dome Theater, where a five-story, wraparound screen makes every film an immersive experience; and the Henry Crown Space Center, where you can see the real Apollo 8 module that circled the moon in 1968.

A Miniature World of Wonder: Tucked inside the museum, just past the world's largest pinball machine, is a magical, miniature treasure: the Fairy Castle. Built by Hollywood craftspeople and artists for silent film star Colleen Moore, this opulent doll house toured the country during the Great Depression before finding a home at the museum in 1949. The doll house's lavish details include the chapel's real stained-glass windows, the great hall's curved, gilded staircase, and the library's 65 tiny volumes penned by famous authors.


Chicago is a fantastic destination for live theater, music and comedy. There are so many choices and venues that we can't even begin to scratch the surface here. However, below are three options for visitors that are available year-round.

Second City Comedy Club (historic Old Town)

The Second City Comedy Club opened its doors on a snowy Chicago night in 1959. Since then, it has grown to become the world's premier comedy club, theater and school of improvisation. Notable alumni include Dan Aykroyd, John Belushi, Steve Carell, Stephen Colbert, Tina Fey, Eugene Levy, Jane Lynch, Bill Murray, Mike Myers, Catherine O'Hara, Gilda Radner, Harold Ramis, Amy Sedaris, Martin Short, George Wendt and Fred Willard, among many others. Wow!

Each show is an unpredictable roil of raw talent. You might not discover the next Saturday Night Live regular when you visit, but you're guaranteed a lot of laughs.

Buddy Guy's Legends (South Loop)

One of Chicago's true cultural landmarks, Buddy Guy's Legends is also the city's premier blues club. It is owned by Rock and Roll Hall of Famer Buddy Guy, the winner of seven GRAMMY Awards, a 2015 Lifetime Achievement GRAMMY Award, 37 Blues Music Awards (the most any artist has ever received), the Billboard Magazine Century Award for distinguished artistic achievement, a Kennedy Center Honor, and the Presidential National Medal of Arts. Rolling Stone Magazine ranked him #23 on its list of the "100 Greatest Guitarists of All Time"—just to call out a few of his honors.

Buddy Guy is a genuine American treasure and one of the final surviving connections to an historic era in the United States' musical evolution. Fulfilling a promise he made to his friend Muddy Waters (the noted American blues singer-songwriter and musician who is often cited as the "father of modern Chicago blues"), Buddy Guy is keeping the blues alive. His club has been booking some of the best local and national blues bands seven nights a week for 20 years.

Gospel Brunch at House of Blues (River North)

A chain restaurant might seem like an odd addition to this list, but the Gospel Brunch at House of Blues is a blast. Dig into a signature all-you-can-eat breakfast buffet featuring favorite dishes from the South: chicken and waffles, savory biscuits and gravy (everything's better with gravy), Cajun shrimp and more. Once you've filled your plate, settle in for an uplifting Gospel concert that is both moving and energizing. Before you know it, you'll be clapping, stamping your feet and waving your napkin in the air. When I visited, there was a point in the program where the MC pulled a dozen or so audience members up onto the stage for a dance-off. So, if you don't enjoy the limelight, make sure your party includes at least one good sport who's willing to take one for the team. (Due to COVID, the Gospel Brunch is on a temporary hiatus. Please check the House of Blues website for its return.)


Choose Chicago has an excellent online Food and Drink Guide that is easy to navigate and chock-full of delicious options. I do recommend exploring the site on a full stomach. Otherwise, it's kind of torture.

If you're not from the Midwest, here are a few local delicacies you might want to try:

Chicago-style Hot Dogs—Typically topped with mustard, relish, onions and peppers—but never ketchup. While there are as many places to try them as there are variations on the combination of condiments, I recommend checking out the dogs at Gene & Jude's, Hot Doug's, Portillo's, Phil's Last Stand or Wolfy's. Seriously, though, don't even think about asking for ketchup!

Italian Beef Sandwich—Al's #1 Italian Beef (for some historical flair, try the restaurant's original location on Taylor Street) constructs its sandwich with seasoned (lots of garlic) beef piled high on a crusty French roll and then dipped—the entire sandwich—into a vat of hot, meaty au jus. Top with a spoonful of sweet peppers and spicy giardiniera (Italian pickled veggies) and you're ready for some juicy-oozy, drip-down-your-arm goodness.

Deep-dish Pizza—Cheese on the bottom, sauce on top. Order one at Bartoli's, Giordano's or Lou Malnati's. (Because the fierce rivalry over the best pizza in Chicago runs far deeper than the crusts, the suggested restaurants are listed in an unbiased alphabetical order.)

Garrett Popcorn—You'll see a lot of travelers boarding flights for home with a tin of Garrett's popcorn clutched tightly in their hands. Popping for over 70 years, Garrett's knows its corn. There are a ton of flavors to choose from, but Garrett's Mix (half caramel, half cheese-flavored) is the best for those who crave a little salt with their sweets.

The Original Rainbow Cone—Five flavors of ice cream stacked high. Since 1926, Rainbow Cone has been scooping and stacking the same five flavors in the same order: (from top to bottom) orange sherbet, pistachio, Palmer House (New York Vanilla with cherries and walnuts), strawberry and chocolate.


Chicago CityPASS® Tickets

Save half off combined admission to Chicago's top attractions with a Chicago CityPASS® ticket. Each ticket includes prepaid entry to five attractions, including Shedd Aquarium, Skydeck Chicago, the Field Museum and any two of the following: the Art Institute of Chicago, Museum of Science and Industry or 360 CHICAGO observation deck. (Note: Once Adler Planetarium reopens fully in early 2022, it will again become one of the option attractions on Chicago CityPASS® tickets.)

Chicago CityPASS® tickets can be ordered online and are delivered moments later to your email. You can save the tickets to the Apple Wallet on your smartphone or simply leave them in your email. Once you begin using your tickets, you have nine consecutive days to use the remaining admissions. That generous time allowance lets you spend a full day exploring each attraction while still leaving plenty of time to discover other parts of the city.

Chicago Style on a Budget

Choose Chicago offers tips on how to explore the Windy City while still being frugal. Browse lists of free activities and attractions, inexpensive hotels and do-it-yourself walking tours.


Chicago is a great walking city, but you will need transportation (Lyft, taxi or transit) to get to some neighborhoods and attractions. One option is a Ventra Card, a contactless and convenient way to pay for rides on Chicago Transit Authority (CTA) buses and Pace trains. The Ventra app has a trip-planning tool to help get you from point A to point B. You can even load your virtual card onto your iPhone, Apple Watch or Android phone, which makes paying a quick tap and go.

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