Chicago, the Windy City, is a vibrant metropolis that offers a mix of stunning architecture, world-class museums, and a rich cultural scene. Nestled on the shores of Lake Michigan, Chicago is known for its iconic skyline, deep-dish pizza, and famous attractions like Millennium Park and the Art Institute of Chicago. Whether you’re exploring the historic neighbourhoods, strolling along the Riverwalk, or catching a game at Wrigley Field, Chicago has something for everyone. But with so many amazing cities in the USA, you might wonder: is Chicago worth visiting? In this post, we’ll explore what makes Chicago special and help you decide if it’s the right destination for your next adventure.
Table of Contents
Pros – Reasons You Should Visit Chicago
1. A Stunning Skyline with Iconic Architecture
Chicago is home to one of the most impressive skylines in the world, with towering skyscrapers lining the shores of Lake Michigan. The city has been a leader in architectural innovation for over a century, and its blend of historic and modern buildings creates a breathtaking urban landscape. From the Willis Tower (formerly the Sears Tower) to the neo-Gothic Tribune Tower and the ultra-modern Aqua Tower, Chicago is a dream destination for architecture lovers.
One of the best ways to appreciate the city’s skyline is by taking the Chicago Architecture River Cruise. As I floated along the river, a guide explained the history behind the city’s most famous buildings, making the experience both scenic and informative. Watching the skyline light up at night from Navy Pier was another unforgettable moment—the city feels alive with energy, and the reflections on the water make for an incredible view.
2. Deep-Dish Pizza and an Unmatched Food Scene
Chicago is famous for its deep-dish pizza, a thick, cheesy, sauce-topped creation that’s unlike anything you’ll find elsewhere. But beyond pizza, the city has one of the best and most diverse food scenes in the United States, offering everything from classic steakhouses to Michelin-starred restaurants and an incredible range of international cuisine.
I had my first deep-dish experience at Lou Malnati’s, and it was worth every bite—the buttery crust, gooey cheese, and rich tomato sauce made for a pizza that was as much a meal as an event. But Chicago’s food scene isn’t just about pizza. The city is also famous for its Italian beef sandwiches, Chicago-style hot dogs, and an incredible selection of fine dining spots. Whether you’re in the mood for upscale dining or classic street food, Chicago has something for every palate.
3. Millennium Park and the Famous “Bean”
One of the most photographed landmarks in Chicago is Cloud Gate, more commonly known as “The Bean.” Located in Millennium Park, this massive, reflective sculpture has become a symbol of the city, drawing visitors who want to snap photos of its mirrored surface, which reflects the skyline and people around it.
I visited on a sunny afternoon, and the way the city’s buildings curved and distorted on the Bean’s surface was mesmerizing. Beyond the sculpture, Millennium Park itself is a fantastic place to relax, with beautiful gardens, fountains, and outdoor art installations. In the summer, you can catch free concerts at the Jay Pritzker Pavilion, while in winter, the park transforms into a festive wonderland with ice skating and holiday lights.
4. The Museum Scene is One of the Best in the U.S.
Chicago is home to some of the most prestigious museums in the country, covering everything from fine art and natural history to science and contemporary exhibits. The Art Institute of Chicago, with its world-famous collection that includes works by Van Gogh, Monet, and Picasso, is a must-visit for art lovers. The Field Museum houses a massive collection of natural history artifacts, including “Sue,” the largest and most complete T. rex skeleton ever discovered.
I spent an entire day at the Art Institute and still felt like I hadn’t seen everything. Walking through the museum’s grand halls, I was amazed at how many masterpieces were on display. The Field Museum was another highlight, especially the impressive dinosaur exhibit. Whether you’re into art, science, or history, Chicago’s museums are among the best in the world.
5. Lake Michigan and the City’s Beautiful Waterfront
Unlike many big cities, Chicago has the unique advantage of sitting right next to one of the largest freshwater lakes in the world. Lake Michigan provides miles of scenic shoreline, beaches, and walking paths that offer a perfect escape from the busy urban environment.
I spent an afternoon walking along the Lakefront Trail, which stretches for miles along the shore and offers incredible views of both the water and the skyline. North Avenue Beach was another highlight, where I got to relax on the sand while still feeling like I was in the heart of the city. Whether you want to go for a swim, rent a bike, or just take in the view, Chicago’s waterfront is a huge part of what makes the city special.
6. A Passionate Sports Culture
Chicago is one of the best cities in the U.S. for sports fans, with legendary teams across multiple major leagues. Whether it’s catching a Cubs game at Wrigley Field, watching the Bulls at the United Center, or seeing the Bears play at Soldier Field, the city’s sports culture is deeply ingrained in its identity.
I was lucky enough to see a game at Wrigley Field, one of the most historic baseball stadiums in the country. The energy of the fans, the smell of hot dogs in the air, and the classic feel of the stadium made it an unforgettable experience. Even if you’re not a big sports fan, the passion Chicagoans have for their teams is infectious and adds to the city’s lively atmosphere.
7. A Legendary Music Scene, Especially for Blues and Jazz
Chicago has a deep musical history, particularly in blues and jazz, which have shaped the city’s cultural landscape for decades. Legendary clubs like Buddy Guy’s Legends and Kingston Mines still host incredible live performances, keeping the city’s music traditions alive.
I spent an evening at a small blues club in the South Loop, and it felt like stepping back in time. The musicians were incredibly talented, and the intimate atmosphere made it feel like a personal performance. Whether you’re into jazz, blues, rock, or hip-hop, Chicago’s music scene has something for everyone, and catching a live show is a must while in the city.
8. A City of Neighborhoods, Each with Its Own Character
Chicago is made up of dozens of diverse neighborhoods, each offering a unique atmosphere and experience. The Loop is home to skyscrapers and cultural attractions, while areas like Wicker Park and Logan Square are known for their indie cafés, street art, and trendy bars. Chinatown, Pilsen, and Little Italy provide incredible cultural and culinary experiences that showcase the city’s diversity.
I spent a day exploring Pilsen, a historically Mexican neighborhood filled with colorful murals and some of the best tacos I’ve ever had. Later, I wandered through Lincoln Park, with its historic brownstones and free-entry zoo. Each neighborhood felt like a different city within the city, offering something new and exciting to discover.
9. The Magnificent Mile and World-Class Shopping
For those who love shopping, Chicago’s Magnificent Mile is a dream destination. This stretch of Michigan Avenue is lined with designer boutiques, department stores, and flagship shops, making it one of the best shopping streets in the country. Even if you’re not into shopping, the area is great for strolling and taking in the energy of the city.
I walked the Magnificent Mile on a weekend, and the mix of elegant storefronts, towering buildings, and street performers created a dynamic atmosphere. With everything from luxury brands to local shops, it’s easy to spend hours browsing and people-watching.
10. Chicago’s Famous Comedy Scene
Chicago is known for producing some of the greatest comedians of all time, thanks to institutions like The Second City and iO Theater. Many of today’s biggest comedy stars got their start in Chicago, and the city’s improv and stand-up comedy scene is still thriving today.
I caught a show at The Second City, and it was one of the funniest live performances I’ve ever seen. The mix of improvisation, sketch comedy, and audience interaction made it a night to remember. If you enjoy comedy, seeing a show in Chicago is an experience you shouldn’t miss.
Cons – Things to Consider When Visiting Chicago
1. Harsh Winters with Freezing Temperatures and Strong Winds
Chicago is infamous for its brutal winters, with freezing temperatures, heavy snowfall, and the relentless “Windy City” gusts that make it feel even colder. From December to March, the city experiences subzero wind chills, icy sidewalks, and occasional blizzards that can make exploring uncomfortable and even dangerous.
I visited Chicago in January, and stepping outside felt like walking into a freezer. The wind coming off Lake Michigan cut through every layer of clothing I had on, and even short walks between attractions became a battle against the elements. While the city is well-equipped to handle snow with an efficient plowing system, flights can still get delayed, and public transport sometimes struggles in extreme weather. If you’re not used to harsh winters, visiting Chicago in the colder months can be a real challenge.
2. High Costs for Accommodation, Parking, and Attractions
Chicago is one of the most expensive cities in the U.S., particularly when it comes to hotels, dining, and parking. While there are budget-friendly options, staying in the downtown area can be pricey, with hotels charging high rates, especially during peak seasons and major events. Parking is also notoriously expensive, with downtown garages charging upwards of $50 per day, and street parking being difficult to find.
I stayed in a mid-range hotel near the Loop, and while the location was convenient, the price per night was much higher than I had expected. Even parking for a few hours at a garage near Millennium Park cost nearly as much as a meal at a good restaurant. If you’re visiting on a budget, staying in a neighborhood outside the downtown core and using public transport can help cut costs, but expect to spend more here than in other Midwest cities.
3. Traffic and Congested Roads Can Be Frustrating
Driving in Chicago can be a nightmare, with heavy traffic, confusing intersections, and aggressive drivers making it stressful for visitors unfamiliar with the city. The highways leading into downtown, particularly the Dan Ryan Expressway and the Kennedy Expressway, are frequently congested, especially during rush hour.
I made the mistake of renting a car to explore the city, and I quickly regretted it. Navigating the busy streets was stressful, and finding parking was even worse. What should have been a short 15-minute drive from my hotel to a museum turned into a frustrating, hour-long crawl through bumper-to-bumper traffic. If you’re visiting, I highly recommend skipping the car rental and relying on the city’s efficient public transport system instead.
4. Crime and Safety Concerns in Certain Areas
Like any major city, Chicago has areas with higher crime rates, and while the tourist-friendly parts of the city are generally safe, some neighborhoods can be risky, particularly at night. The city’s reputation for crime is often exaggerated in the media, but visitors should still take standard precautions, such as avoiding poorly lit areas and being aware of their surroundings.
While I never felt unsafe in downtown Chicago, I did notice that some areas felt less inviting after dark. Locals advised me to be cautious in certain neighborhoods and to stick to well-traveled areas if walking at night. The key to enjoying Chicago safely is to research which areas to avoid and use common sense, just as you would in any large metropolitan area.
5. The Summer Heat and Humidity Can Be Uncomfortable
While Chicago is known for its cold winters, summers can be surprisingly hot and humid. From June to August, temperatures can soar above 90°F (32°C), with high humidity making it feel even hotter. The combination of heat, crowds, and urban concrete can make sightseeing during peak summer afternoons exhausting.
I visited during a July heatwave, and walking around the city in the afternoon sun quickly became draining. Even sitting on an outdoor patio felt uncomfortable, as the heat reflected off the pavement. Luckily, there are plenty of indoor attractions like museums and shopping centers to escape the heat, but if you don’t handle high temperatures well, visiting in spring or autumn is a much better choice.
When to Visit Chicago
The best times to visit Chicago are spring (April to June) and autumn (September to October), when the weather is mild, and the city’s parks and lakefront are at their best. These months are perfect for exploring the Magnificent Mile, Millennium Park, and outdoor festivals. Summer (July to August) offers warm weather and bustling attractions, though crowds peak during this season. Winters (December to February) are cold and snowy, but the city’s holiday decorations and indoor cultural experiences, like the Art Institute of Chicago, make it an appealing time for visitors who don’t mind the chill.
How to Get to Chicago
Chicago is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). O’Hare, located 17 miles northwest of downtown, offers extensive domestic and international connections, while Midway, closer to the city centre, primarily handles domestic flights. From O’Hare, the CTA Blue Line train provides an affordable and direct route to downtown. From Midway, the CTA Orange Line is similarly convenient. Taxis, ride-hailing apps, and airport shuttles are also available, though pricier. Amtrak trains and intercity buses also connect Chicago to regional hubs, with Union Station being the main terminal.
Where to Stay in Chicago
Chicago offers a diverse range of accommodations for every budget:
- Luxury: The Loop or Gold Coast – Stay at The Peninsula Chicago, offering five-star amenities and rooftop dining, or The Langham Chicago, known for its stunning river views and elegant interiors.
- Mid-range: River North or Streeterville – Try Hotel EMC2, a boutique gem near the Magnificent Mile, or The Cambria Hotel Chicago Loop, combining comfort and a central location.
- Budget: South Loop or Lincoln Park – Consider HI Chicago Hostel, an affordable option near Millennium Park, or The Willows Hotel, a cosy stay in a vibrant neighbourhood.
Getting Around Chicago
Chicago’s extensive public transport system is affordable and efficient. The Chicago Transit Authority (CTA) operates the L trains and buses, which cover the city and suburbs. Purchase a Ventra Card for unlimited rides during your stay. Walking is an excellent option in areas like the Loop and along the Riverwalk, while bike enthusiasts can use the Divvy bike-share program to explore the lakefront trails. Taxis and ride-hailing apps like Uber and Lyft are readily available but best reserved for short trips or late-night rides. For a unique perspective, hop on a Chicago River architectural boat tour.
How Long to Spend in Chicago
Three to four days is ideal to explore Chicago’s diverse attractions. Spend the first day visiting landmarks like Millennium Park, the Art Institute of Chicago, and the Willis Tower Skydeck. Dedicate the second day to exploring the Magnificent Mile and Navy Pier, with an evening spent at a world-class theatre or comedy show. On the third day, head to Lincoln Park Zoo and the Chicago History Museum, or venture into neighbourhoods like Wicker Park for local charm. With extra time, take a day trip to Oak Park to see Frank Lloyd Wright’s architecture or relax on the shores of Lake Michigan. Chicago’s mix of culture, history, and urban energy makes it a must-visit destination.
Conclusion
So, is Chicago worth visiting? Absolutely! If you’re a fan of iconic architecture, vibrant cultural scenes, and delicious food, Chicago is a must-see. Its blend of historic charm and modern attractions makes it one of the most dynamic cities in the USA. While it’s known for its brisk winters, the city’s charm shines year-round, especially during its lively summers. For travellers seeking a destination with a mix of urban excitement and Midwestern warmth, Chicago is a city that will leave you inspired and eager to return.