7 Unforgettable Reasons to Add Chicago to Your Travel Bucket List
It’s no surprise to me, as someone who has worked and toured there, that Chicago ranks 11th on Time Out’s Annual Best 50 Cities In The World. Taking into account culture, dining experiences, nightlife, world-class museums and music performances, among others, Chicagonians are proud of their city and happy to live there, despite what recent media depictions might say.
For tourists, the city offers a dazzling array of entertainment and unique experiences to enjoy. From family-friendly to unique romantic dinner alcoves and historical tours to the opera, there is virtually something for everyone. The city sparkles with splendid architecture and decadent bridges while showcasing the reflection of sleek buildings echoed in the rivers and lake below.
With modern accessibility and a well-thought-out transit system that includes trains, Els, buses, taxis, rentable bikes and ride shares, Chicago is easy to get around. The city’s grid-like street structure runs North and South and East to West, beginning at the shores of beautiful Lake Michigan. Even I, possessing possibly the world’s most terrible sense of direction, can find my way around.
The Number 1 Reason To Visit Chicago: Shopping
Michigan Avenue, dubbed the Magnificent Mile, is home to over 400 retailers, ranging from high-end luxury brands like Tiffany and Dior to local artisan shops and whimsical experiences at the Harry Potter Shop, the Lego Store and American Girl. Set parallel along the deep-blue shores of Lake Michigan, over winding canals, exquisite landscapes, street vendors and opulent architecture, a trip to Chicago without visiting the Magnificent Mile would be like visiting Paris without exploring the Champs-Élysées.
For the ultimate Chicago shopping expedition, start at the South end at Wabash and Madison (just one block West of The Bean) and explore the legendary Jeweler’s Row. Featuring over 20 retailers showcasing one-of-a-kind designs, you’ll sparkle with inspiration and get in the spirit for perusing the shops along the Magnificent Mile.
Walk one block right to Michigan Avenue and move North among well-known retailers like Zara, Nike and Bloomingdale’s. Enjoy custom service at luxury brand stores like Zegna, Gucci and Louis Vuitton, where you can expect exquisitely tailored clothes and accessories, guaranteed to elevate your wardrobe.
Insider Tips & Favorites:
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Garret’s– a Chicago staple for mouth-watering popcorn has outlets along the way. Combine sultry with sweet when you order the ‘Chicago Mix’ for a true windy city treat while you shop the Magnificent Mile.
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The Chicago Sports Museum- Located on the 7th floor of Water Tower Place adjacent to the legendary Harry Caray’s restaurant, this must-see sports museum boasts of unique Chicago teams’ apparel and memorabilia.
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The American Girl Store- Let your inner child come alive at this life-like store featuring a variety of dolls from different areas and cultures worldwide. Dine with your doll or get expert doll care at the hospital that offers interactive X-rays, eye charts and more.
Insider Tips & Favorites:
- The Art Institute conveniently offers same-day reentry so you can grab lunch or a quick break and go back inside.
- At Willie Dixon’s Blues Heaven Foundation, book a ticket ahead online for the West Side Showroom featuring live music.
Don’t underestimate the Field Museum, home to over 40 million historical objects ranging from full dinosaur skeletons to mummies in an Ancient Egyptian burial chamber.
2: Chicago Is Home To Many Top-Rated Museums and Tours
Many world-class museums displaying Art, Music, Sports and History are peppered throughout Chicago, with several located along the Michigan Mile. Most notably, the Art Institute of Chicago, flanked by bronze lions symbolizing strength and worldly wisdom, sprawls across 10 city blocks in Grant Park. Founded in 1879, the classical museum we know is widely regarded as the oldest and largest in the United States.
Home to several distinct collections from African Art to the Bronze Age and masterpieces depicted by highly-lauded impressionists like Van Gogh to leading Cubist painters like Picasso, here a few of the highlights from the Art Institute’s immense collection:
Willie Dixon’s Blues Heaven Foundation is in the historic Chess Records building at 2120 S. Michigan Avenue. The museum showcases the emergence and growth of blues music throughout Chicago. The Blues initially found its way to Chicago in the 1920s, as Jim Crow laws and other influences led to the Great Migration, during which many African Americans moved North. With them, they brought southern musical influences such as Delta Blues (emerging from Mississippi) combined with acoustic guitars, harmonicas and soulful lyrics. Artists like Muddy Waters and Buddy Guy are names synonymous with the growth of the Blues genre.
The museum features black and white photo galleries, insights into Chess Records recording studio and tributes to modern-day Blues musicians who have incorporated the Blues style, like Eric Clapton and The Rolling Stones.
Number 3: Sports, Sports & More Sports
Whether you’re a hockey fan, baseball fanatic or are into College or NFL football, Chicago is home to some of the best teams and stadiums in the league. Take in a Cubs game at the historic Wrigley Field. Root for the multi-time Stanley Cup winners or the legendary Chicago Bulls at the United Center. Cheer on the Bears at Soldier Field or attend the annual Chicago Marathon, considered one of the top-tier marathons in the country.
If watching a game at a Chicago Sports Bar is more your style, Harry Caray’s, named after the great Cubs Announcer, has two locations, one downtown and the other at Navy Pier. Another great option is Miller’s Pub in the loop. Established in 1935, this renowned restaurant hosted celebrities like Marilyn Monroe and Jimmy Durante, as well as Bill Veeck, who as president of the Cubs, was responsible for innovations like fireworks and planting the ivy on the walls of Wrigley Field.
Insider Tips & Favorites:
- Avoid traffic to Wrigley by taking the Red Line to the nearby Addison Station.
- Soldier Field is a cashless venue and requires clear bags and high security. Check their policies before you go!
- The Atrium at the United Center features the world-renowned statue of Michael Jordan and the MadHouse Team store.
Insider Tips & Favorites:
- For a unique experience with views, visit the Palm Court at the Drake hotel for a full afternoon tea.
- If a refined bar and divine Midwest cuisine are your thing, the Brass Tack with top mixologists will not disappoint.
- For deep-dish pizza with a caramelized crust, try the lesser-known Chicago restaurant Pequads and elevate your pizza game.
Superb Dining By Renowned Chefs Offering Varying Cuisine Is The Number 4 Reason To Put A Trip To Chicago On Your Bucket List
Speaking of dining, while Chicago is best known for its deep-dish pizza, it’s also home to Michelin-starred restaurants and eclectic cuisine from around the world. In the West Loop, visit Girl And The Goat for delectable smoked meat, refined vegetables and hors durves. Travel to River North for Mexican cuisine by top-rated Chef Rick Bayless. His flagship Frontera Grill is brimming with flavors, fresh ingredients that will delight your taste buds. I highly recommend the Tortilla soup and the CREEKSTONE FLANK steak* marinated in garlic & spices.
Known as Chicago’s best burger and for its crispy bologna sandwich, Au Cheval should be on your bucket list. I can personally attest to the intense flavors of their food. Go early, as they don’t take reservations and sometimes have lines outside the door.
5: Chicago Boasts A Unique History, Ranging From The Worldwide Explosion of Candy By The Wrigley Family To The Many Legends Of Al Capone
One of the best ways to explore the storied history of the windy city is on the water. A number of architectural tours with knowledgeable guides parade along the canals and the Chicago River. Learn never-before-heard details about the Chicago Fire, why the city reversed the flow of the River, the Wrigley Building and more.
The Wrigley Building itself is fascinating. Originally built in 1921 as the headquarters of the Wrigley dynasty, it boasts Chicago’s first skyscraper. An iconic blend of Spanish Colonial Revival and French Renaissance, today it houses high-end furniture and luxury stores, a food court, offices and event spaces.
Insider Tips & Favorites:
- Dress in layers for the Chicago Architectural Boat Tour. It tends to get windy and chilly, even in the summer.
- For a true Al Capone experience, the Exchequer Restaurant & Pub, formally known as the 226 Club, was his favorite restaurant in the city. With its speakeasy and tunnels, it was a place for quick escape.
- The historic Union Station, with its grand colonnades and limestone walls, is free to visit as a unique Chicago experience. Filmed in movies like The Untouchables and My Best Friend’s Wedding, you’ll be sure to recognize the grandeur of the elegant cinematic backdrop.
Insider Tips & Favorites:
- You’re best off finding paid parking and then hopping on the CTA or a rideshare to Navy Pier.
- The Millennium Park Ampitheater, otherwise known as the Jay Pritzker Pavilion hosts world-class performances throughout the year.
- The downtown Riverwalk is another attraction not to miss. Grab a coffee or pastry and take in gorgeous views of the city.
Unique Attractions Like Navy Pier & Millennium Park Are The Number 6 Reason Why Chicago Attracts Tourists From All Over The World
Drawing in over 9 million visitors annually, Navy Pier is Chicago’s second most visited tourist attraction. The 3300-foot-long pier was built as a ship dock, but even in its early days, it hosted outdoor expos. Today, the pier lies in pristine condition, extending over Lake Michigan. Dozens of restaurants, retail shops and carnival rides are available. Visitors can take in a show at the Chicago Shakespeare Theater or explore the Children’s Museum, both located on the immense pier.
Known as “the front lawn” of downtown Chicago, Millennium Park is situated between the Art Institute and Grant Park. It features the famed Crowned Fountain, Lurie Gardens, Pritzker Pavilion and The Bean. In the warmer months, kids and adults alike can explore the Maggie Daley Park for rock climbing, picnics and more. During the winter, an ice trail winds around the park, giving skaters a place to glide along in the brisk outdoors.
7: The Beauty Varies By Season & Is Splendid Anytime Of The Year
Lastly, no matter when you visit, Chicago is beautiful any time of the year. From fresh tulips planted along the city in the spring to decadent Christmas displays, water views and a gorgeous skyline. Also hailed as one of the cleanest cities in America, Chicago embodies a spirit and beauty unique to itself.
