Unveil the Architectural Wonders of the Windy City
As an avid traveler, I’ve seen some incredible skylines, but Chicago’s is a jaw-dropper. The city is renowned for its stunning architecture, and a visit to Chicago is incomplete without admiring these iconic structures. Two of the most famous buildings you must visit are the Willis Tower, formerly known as Sears Tower, and the John Hancock Center. The Willis Tower’s Skydeck offers breathtaking views of the city from 1,353 feet above ground, while the 360 CHICAGO Observation Deck at the John Hancock Center lets you soak in panoramic views.
For an immersive experience, take an architectural boat tour down the Chicago River. Companies like Chicago Architecture Foundation Center River Cruise and Wendella Tours & Cruises offer insightful tours guided by experts who share the history and stories behind the city’s magnificent buildings.

Indulge in the Legendary Deep-Dish Pizza
Chicago’s deep-dish pizza is legendary, and as a foodie, I can confirm that it’s worth the hype. The Windy City is home to numerous pizzerias serving this mouthwatering treat, but my personal favorite has to be Pequod’s Pizza. Their caramelized cheese crust is simply divine! Other popular deep-dish pizza joints include Lou Malnati’s and Giordano’s. Make sure to arrive early or be prepared to wait, as these famous spots tend to have long lines.
Immerse Yourself in Chicago’s World-Class Museums
Art and history buffs will love Chicago’s rich array of world-class museums. The Art Institute of Chicago, for instance, houses an extensive collection of artworks spanning thousands of years. Be sure to check out Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jette.”
The Field Museum and the Museum of Science and Industry offer immersive and interactive experiences for all ages. If astronomy interests you, the Adler Planetarium is a must-visit, with fascinating exhibits and an incredible view of the Chicago skyline from its terrace.
Stroll Through Chicago’s Beautiful Parks and Gardens
Chicago’s parks and gardens are perfect for unwinding and soaking in the city’s natural beauty. Millennium Park, located in the heart of downtown, is a favorite among locals and tourists alike. The park is home to the famous Cloud Gate sculpture, affectionately known as “The Bean,” and the stunning Lurie Garden.
The Lincoln Park Zoo and Conservatory, a haven for nature lovers, offers free admission and features a beautiful botanical garden, as well as diverse wildlife exhibits. It’s a great place for a leisurely stroll or a family day out.

Groove to the Tunes of Chicago’s Iconic Music Scene
Chicago has a rich musical heritage, particularly in the realms of jazz and blues. Music enthusiasts should not miss live performances at Buddy Guy’s Legends and Kingston Mines, two of the city’s most iconic venues. Additionally, the Chicago Symphony Orchestra is internationally renowned and regularly features guest artists from around the world.
If you’re in town during the summer, be sure to catch music festivals like Lollapalooza and the Chicago Jazz Festival, which showcase a diverse array of genres and talents.
Shop ‘Til You Drop on the Magnificent Mile
For shopping enthusiasts, Chicago’s Magnificent Mile is a dream come true. This bustling stretch of Michigan Avenue features upscale shopping destinations like Water Tower Place and 900 North Michigan Shops, offering luxury brands and department stores. However, if you’re on a budget, fret not! Nordstrom Rack and other discount stores in the area offer stylish finds at wallet-friendly prices.
While shopping, be sure to explore local boutiques and hidden gems that showcase Chicago’s unique fashion scene. You’ll find everything from designer brands to local artisans, making it the perfect place to shop for souvenirs and one-of-a-kind finds.

Experience Chicago’s Vibrant Theater Scene
Chicago’s theater scene is world-class, offering a wide range of performances from Broadway-style productions to cutting-edge experimental theater. Catch a show at the iconic Chicago Theatre, or check out smaller venues like the Goodman Theatre and Steppenwolf Theatre Company for intimate, thought-provoking performances. For a memorable night out, be sure to catch a performance at Second City, the famous improv comedy club that has launched the careers of legends like Tina Fey, Bill Murray, and Steve Carell.
Take a Bite Out of Chicago’s Diverse Culinary Landscape
Beyond deep-dish pizza, Chicago’s culinary scene is incredibly diverse and delicious. As a food lover, one of my most memorable experiences was exploring the flavors of the city’s ethnic neighborhoods. Devour authentic Mexican cuisine in Pilsen and Little Village, or savor delicious Middle Eastern dishes in Albany Park.
For a truly unique experience, head to the West Loop neighborhood, where acclaimed restaurants like Girl & the Goat and Au Cheval serve up innovative dishes that will delight your taste buds. Don’t forget to make reservations in advance, as these hotspots fill up quickly!
Cheer on Chicago’s Beloved Sports Teams
Chicago is a sports lover’s paradise, with passionate fans cheering on their beloved teams across various leagues. Catch a Chicago Cubs game at historic Wrigley Field, or head to the South Side to watch the White Sox in action. For basketball and hockey enthusiasts, the United Center is home to the Chicago Bulls and the Chicago Blackhawks, respectively.
No matter the season, there’s always an exciting game to watch and a lively atmosphere to enjoy, making it the perfect way to experience the city’s sports culture firsthand.
Unwind at Chicago’s Beautiful Beaches
While it might surprise some, Chicago boasts stunning beaches along its Lake Michigan shoreline. During the summer months, North Avenue Beach and Oak Street Beach are popular spots for sunbathing, swimming, and beach volleyball. The picturesque lakefront also offers walking and biking paths, providing a scenic and relaxing way to explore the city’s natural beauty.

Time to Plan Your Chicago Adventure
With so much to see and do, it’s no wonder that Chicago is a top destination for luxury travelers on a budget. From world-class museums and delectable dining experiences to beautiful parks and a thriving music scene, the Windy City offers endless opportunities for unforgettable experiences. Join the Classy On A Coin travel community and sign up for our newsletter to receive insider tips, destination guides, and budget-friendly recommendations that will elevate your travel experiences.
Happy Travels! – Anderson




