Chicago is a breath-taking city known for its impressive architecture. The streets are clean and not overly crowded, though homelessness is present in some areas during the day. Be aware of tornado warnings, as they can occur. Fortunately, the city has an excellent public transport system, with buses and subways making it easy to get around.
Places of Interest
Jay Pritzker Pavilion
This outdoor amphitheatre is perfect for free entertainment. During the day, you can watch rehearsals for upcoming performances. I was lucky enough to witness a full orchestra performing—an unforgettable experience.
The Big Bean
Near the amphitheatre is the famous Cloud Gate, often called “The Bean.” This reflective sculpture is one of the most iconic spots in Chicago, perfect for capturing a unique souvenir photo.
Ukrainian Village
We spent a lot of time in Ukrainian Village, which felt unusual compared to the UK, where neighbourhoods dedicated to one nationality are rare. It’s about a 30-minute bus ride from Water Tower Place and features Ukrainian social clubs, a cathedral, a church, wall murals, a museum, a school, and various shops and restaurants. Even in the supposedly American CVS pharmacy, the staff were speaking Ukrainian—one, named Dorothy, was even American-born! Saints Volodymyr & Olha Ukrainian Catholic Church is one of the most beautiful churches I’ve visited, with stunning iconography. Services are held throughout the day, with even more on Sundays, so it’s worth checking out if you’re a believer.
We also attended an event at the American Ukrainian Youth Association, where the Ukrainian band SKAI performed. Additionally, an annual village festival takes place here, featuring singing and dancing.
Chicago PD and Chicago Fire Locations
Fans of Chicago PD or Chicago Fire can visit the fire station seen in the shows. The friendly staff invited me inside for a mini-tour, and they even sell merchandise. The police station is nearby but closed to the public. The area also offers an excellent view of Chicago’s skyline, located near a university sports ground in a more suburban setting. The ‘bar’ where characters are featured is also open but this is on the other side of the city.
Navy Pier
This spot provides incredible city views, perfect for capturing amazing photos. The pier also has a small shopping mall and a fairground.
Riverwalk
Walking along the Chicago Riverwalk is stunning, especially at night. You’ll find intimate coves, breezy cafés, wineries, bars, public art, monuments, museums, and boat tours. However, be cautious in very wet weather, as parts of the walkway can become submerged.
Activities
Lincoln Park Zoo
This free-entry zoo features primates, polar bears, big cats, and penguins—plenty to see without spending a penny.
Football Match (Soccer) at Soldier Field
Attending a soccer match at Soldier Field was an eye-opening experience. The halftime entertainment was better than anything I’ve seen in the UK, featuring a CGI race between Chicago’s subway trains—an amusing touch. We even received free shirts and merchandise handed out to every seat. The stadium wasn’t too full, and while the drumming from a nearby stand was a bit much, the experience was still fantastic.
Important note: If you’re attending a U.S. sporting event, bring as little as possible. The bag restrictions were excessive—everything had to be smaller than an A5 sheet of paper and had to be clear, or you had to pay a fee to store your bag in lockers run by external staff. Annoyingly, people inside were allowed to carry huge drums and trumpets!
Boat Tour
A 90-minute architecture boat tour costs around $35 per person, but it’s absolutely worth it. Chicago boasts a variety of architectural styles, and the guide shared fascinating insights about the Great Chicago Fire and how the river’s flow was reversed. An interesting fact: the Wrigley Company originally sold baking powder, and chewing gum was just a freebie—until it became more popular than the powder itself!
Street Markets
This is where the crowds form. Street markets vary by time of year. I had one appear on a Sunday where a whole main road was closed and vendors lined the streets. Something spontaneous which is a nice additional charm to the trip.
Starbucks Reserve Roastery
This is no ordinary Starbucks. Spread across multiple floors, it features a small rooftop terrace, a cocktail bar, a café with food, and a merchandise store—a must-visit for coffee lovers.
Food in Chicago
Chicago is famous for deep-dish pizza, but I personally wasn’t impressed. To me, it was more like a quiche, with an overload of tomato sauce making the balance feel off. Luckily there was an Indian restaurant nearby!
Breakfast: Stan’s Donuts
Our go-to breakfast spot was Stan’s Donuts, a chain offering a variety of breakfast items that hit the spot.
Chicago is a city full of architectural wonders, rich cultural experiences, and incredible activities. Whether you’re walking along the Riverwalk, exploring neighbourhoods like Ukrainian Village, or watching a game at Soldier Field, there’s always something to enjoy!