Ever since watching "My Best Friend’s Wedding" starring Julia Roberts and Cameron Diaz, I’ve been eager to visit Chicago. The iconic images of the Chicago River winding through the city, with boats passing under numerous bridges, left a lasting impression on me. Typically, when I take a city break, I prefer to spend no more than 3-4 hours on a flight to a destination to avoid jet lag and maximise my vacation time. So, a long-haul trip to Chicago was a change from my norm.
After my 8-and-a-half-hour flight, I landed in Chicago and headed to the Moxy Chicago Downtown, my home for the next few nights. Once settled in, I took a stroll around the Downtown area to soak in my first impressions of the city. The hotel's central location made it easy to explore, with the Chicago Riverwalk just a 15-minute walk away whilst Millennium Park was about 25 minutes on foot. Chicago’s efficient public transport system and street grid layout ensured it was easy to navigate. Making my way around the area, I was struck by the city’s cleanliness, thanks to its clever design with 1,900 miles of alleys keeping the scenic parts of a working city, like rubbish disposal, out of sight.
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Exploring the Windy City
My tour of the city started with a visit to Chinatown for an Adventure food tour, which is one of my favourite ways to dive into a new area and discover hidden gems only known to locals. What better way to learn about a culture and the locals than through its food? Guided by a knowledgeable guide, I have the opportunity to learn about the history of the area whilst enjoying the culinary delights. During the 3-hour tour, I immersed myself in the rich history of Chicago’s Chinatown and listened to stories about old Chinatown with a friendly group of tourists whilst sampling dishes such as dim sum, Szechuan dishes and desserts.
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For a budget-friendly alternative to a food tour, the Chicago Greeter tour is an excellent choice. This free experience allows you to explore a specific neighbourhood with a friendly local guide. I had the chance to tour Humboldt Park on the West Side, an area known for its rich Puerto Rican heritage. My guide was a local Chicagoan who took me through the vibrant neighbourhood, which is as diverse as the murals that adorn its walls and the eclectic vibes that fill its streets. We visited the National Museum of Puerto Rican Arts and Culture, and stopped by various Puerto Rican cafes and coffee shops, soaking in the rich cultural atmosphere.
Next, I visited the WNDR Museum, an interactive, multi-sensory art and technology showcase with a simple message; “we are all artists”. The museum encourages visitors to participate and engage with the art, rather than passive onlookers moving through the space, making the experience more memorable than just looking at paintings on walls.
When you're in Chicago, a river cruise is an absolute must. There's no better way to experience the city than from the water, offering a unique perspective of its stunning architecture. I took the Chicago First Lady Cruise, which partners with the Architecture Foundation Center to deliver a deep dive into the history of Chicago's architectural styles over the decades. The cruise features knowledgeable and passionate volunteer guides who provide an engaging, fun, and detailed narrative of the city's buildings, architectural styles, and the stories of the architects behind them. As you glide along the river under Chicago's many bridges, you'll enjoy unobstructed views of the skyline from the open-air deck.
With the purchase of the Chicago CityPASS®, I gained entry to several top attractions, including the Art Institute, the Planetarium, the Skydeck, and 360 Chicago. At the Art Institute, I marvelled at works by Van Gogh, Monet, Picasso, and Edward Hopper’s "Nighthawks." In just 1.5 hours, I got a solid overview of its main collections, though I could have easily spent another 45 minutes exploring. After my museum visit, I headed to Cindy’s Rooftop bar, just a short walk away. It's one of Chicago’s best rooftop bars, offering stunning views of Millennium Park, the lakefront, and beyond. It was the perfect spot to relax and soak in the cityscape after a day of cultural immersion.
Dining
Dining in Chicago is an adventure in itself, offering a diverse and plentiful food scene that can feel a bit overwhelming at first. A good strategy is to start with some highly recommended restaurants near popular attractions and landmarks.
For lunch, Beatnik on the River provides a serene escape from the bustling city, offering views of the Chicago River. Its Bohemian-inspired interiors and gardens make it feel like you've stepped back into the '50s or '60s. For a classic American diner experience, head to Dove’s Luncheonette in Wicker Park. With bar stools, a '60s jukebox, and Southern-inspired Mexican dishes, it’s the perfect spot to snap some retro photos. And, of course, no trip to Chicago is complete without indulging in deep-dish pizza. I visited Giordano’s in Wrigleyville after a stadium tour for an authentic stuffed pizza experience.
For dinner, I had a fantastic time at Daisies restaurant, which has been highlighted by various respectable publications as one of the most exciting places to eat. The concise menu features starters, pasta dishes, and proteins, and the atmosphere was buzzing with energy. Another memorable dinner was at Bar Siena in the West Loop neighbourhood. I enjoyed roasted meatballs and grilled octopus burrata for starters, with a wide selection of pasta, pizza, salads, and meats for the main course. Summer House in the Lincoln Park neighbourhood was also a standout. This self-styled beach house-inspired space features a California-style menu. Dining here feels like being in a greenhouse, with natural light flooding in from the glass roof and greenery all around. The menu focuses on local and sustainable farming, making it a delightful and environmentally conscious dining experience.
Chicago Attractions
Chicago isn’t just about landmarks, brunches, and popular attractions; it offers a variety of experiences to suit different interests. For baseball fans, a tour of Wrigley Field in Wrigleyville is a must. This historic stadium, the second oldest in the majors, opened in 1914. The 90-minute guided tour, led by a passionate fan, takes you behind the scenes to the bleachers, press box, dugout, and field, sharing memorable stories of games and legendary players.
If beer is your thing, don't miss a visit to Goose Island Brewery. Founded in 1988, it’s one of Chicago’s oldest breweries and is located in West Town, a part of the city you might not otherwise explore. Even as someone who isn't a big beer drinker, I found the tour delightful and entertaining, thanks to the enthusiastic guide and welcoming staff. The Taproom, which opened in 2015, serves as a community hub where you can socialise, drink, and meet locals.
For evening entertainment, a night at Buddy Guy’s Legends is a must if you're a blues fan. This legendary club, opened in 1989 by musician Buddy Guy, is still owned and operated by him. It’s a cosy venue with live music, a lively bar, and food and drink. The authentic blues atmosphere is unparalleled.
Comedy lovers will want to check out The Second City, an improvisational comedy theatre that has launched the careers of stars like Tina Fey, Steve Carell, Bill Murray, and Mike Meyers. The show had me laughing out loud with its hilarious skits, many of which involve audience participation, creating an inclusive and fun atmosphere. It was a highlight of my trip and a highly recommended experience.
2024 is a particularly great year to visit Chicago, as the city is celebrating several milestones of its famous landmarks. Millennium Park marks 20 years, The Second City celebrates 65 years, Buddy Guy’s Legends hits 35 years, and there's the annual summer switch-on event at Buckingham Fountain in Grant Park. These celebrations add even more excitement to Chicago’s vibrant music, arts, and culture scene.
