I’ll admit it, Chicago wasn’t a city that had ever been high on my travel wishlist.
Whenever I thought about visiting the United States, places like New York, Los Angeles or San Francisco always came to mind first. But after spending a few days here, I completely understood why so many people fall in love with it.
It has incredible architecture, amazing food, beautiful parks and one of the nicest city waterfronts I’ve ever explored. Even better, many of the main attractions are within walking distance of each other, making it a really easy city to discover at your own pace.
If you’re planning your first visit, here are the best places to visit in Chicago that I think deserve a spot on your itinerary.
Millennium Park and Cloud Gate
If there’s one place I’d tell every first-time visitor to start, it’s Millennium Park.
This was one of the first places I visited after arriving in Chicago, and it instantly made me understand why people love this city. The park has such a welcoming atmosphere. There are people relaxing on the grass, families wandering around, musicians performing and visitors taking photos in every direction. It feels lively without ever feeling overwhelming.
Of course, the biggest attraction here is Cloud Gate, better known as The Bean. Designed by British artist Anish Kapoor, this enormous mirrored sculpture reflects the surrounding skyline, the clouds above and everyone walking past. I knew it was one of Chicago’s most famous landmarks, but I still wasn’t prepared for just how impressive it looks in person.
Most people take a photo in front of it, but don’t forget to walk underneath as well. The reflections on the curved ceiling create some really cool optical illusions, and it’s easily one of the most unique public artworks I’ve seen.
While you’re here, spend some time exploring the rest of Millennium Park too. You’ll come across the colourful Crown Fountain, the striking Jay Pritzker Pavilion, beautifully landscaped gardens and plenty of places to simply sit for a while. It’s one of those Chicago attractions that feels much bigger than you expect, so don’t rush through it.
Chicago Riverwalk
One of my favourite things to do in Chicago didn’t involve buying a ticket or visiting a museum. I loved simply wandering along the Chicago Riverwalk.
Running alongside the Chicago River through downtown, this waterfront promenade is one of those places where it’s easy to lose track of time. You’ll find cafés, restaurants, wine bars, public art, little parks and plenty of benches overlooking the water. Even though skyscrapers surround you, it somehow feels calm and relaxed.
I found myself stopping here several times throughout my trip, whether it was for a coffee in the morning or just to watch the boats cruise past. It’s also one of the best places to admire Chicago’s incredible architecture from ground level.
The river itself played a huge role in shaping the city’s history and growth, but today it’s simply one of the nicest places to spend an afternoon. If you only have a few days in Chicago, I’d definitely make time for it.
The Magnificent Mile
If you enjoy shopping, architecture or simply wandering through a city, chances are you’ll end up spending some time along the Magnificent Mile.
This famous stretch of North Michigan Avenue is packed with luxury shops, department stores, restaurants, rooftop bars and some of Chicago’s most recognisable buildings. Even if shopping isn’t really your thing, it’s worth coming here just to admire the mix of historic architecture and modern skyscrapers.
One building I’d recommend adding to your itinerary is 360 Chicago. Located on the 94th floor of the former John Hancock Center, the observation deck offers incredible views across downtown and Lake Michigan. On a clear day you can even see into neighbouring states.
It’s also a great place to visit around sunset when the city begins to light up below you.
The Art Institute of Chicago
I’m not someone who visits every museum in every city, but I’d genuinely make an exception for the Art Institute of Chicago.
It’s one of the oldest and most respected art museums in the United States, with a collection that covers everything from ancient civilisations to contemporary works. Whether you’re already interested in art or just curious, there’s a really good chance you’ll recognise at least a few of the paintings here.
Some of the museum’s biggest highlights include Nighthawks by Edward Hopper, American Gothic by Grant Wood and Georges Seurat’s enormous masterpiece A Sunday on La Grande Jatte.
The Art Institute of Chicago museum is much bigger than I expected, so I’d recommend setting aside at least a couple of hours rather than trying to squeeze it into a busy afternoon. Before you leave, don’t forget to take a photo with the famous bronze lion statues guarding the entrance.
Navy Pier
I know attractions like Navy Pier can sometimes get labelled as “touristy”, but honestly, I still think it’s worth visiting, especially if it’s your first time in Chicago.
Stretching out into Lake Michigan, Navy Pier has a really fun atmosphere with restaurants, gardens, shops, sightseeing cruises and plenty of entertainment throughout the year.
The highlight for many visitors is the Centennial Wheel, which rises almost 200 feet above the waterfront and offers fantastic views across both the lake and the city skyline.
If you’re visiting during summer, you’ll often find live music, cultural festivals and fireworks on selected evenings. Even if you don’t go on the Ferris wheel, it’s worth walking right to the end of the pier for some beautiful views looking back towards downtown.
Chicago Architecture River Cruise
If you only book one tour while you’re in Chicago, make it the Architecture River Cruise. I can’t tell you how many people recommended this to me before I arrived, and after learning more about it, I completely understand why.
Chicago is famous for its architecture, and this cruise is one of the best ways to appreciate it. As you travel along the Chicago River, knowledgeable guides explain the stories behind more than 50 landmark buildings, including Marina City, Aqua Tower, Tribune Tower, the Wrigley Building and Willis Tower.
Even if you don’t normally get excited about architecture, the way the guides bring the city’s history to life makes it incredibly interesting. It’s one of those experiences that helps you appreciate Chicago on a completely different level.
Lincoln Park
If you need a break from the skyscrapers, Lincoln Park is the perfect place to slow down. Stretching along the edge of Lake Michigan, this huge public park is home to walking trails, gardens, beaches and the Lincoln Park Zoo, which is one of the oldest free zoos in North America.
The zoo is a fantastic stop if you’re travelling with kids, but even adults will enjoy wandering through the grounds and seeing everything from giraffes and lions to penguins and red pandas. Right next door you’ll also find the Lincoln Park Conservatory, a beautiful Victorian glasshouse filled with tropical plants, orchids and seasonal flowers.
Before you leave, make your way towards North Avenue Beach. The skyline views from here are easily some of the best in Chicago.
Chicago Theatre
Even if you never step inside, the Chicago Theatre is one of those landmarks you’ll probably recognise straight away. Its glowing vertical sign has become one of the city’s most photographed sights and looks especially beautiful once the sun goes down.
The Chicago theatre first opened in 1921 and has welcomed countless legendary performers over the decades. Today it still hosts concerts, comedy shows and touring productions throughout the year.
If your schedule allows, I’d definitely recommend joining one of the guided tours. You’ll get to see the grand lobby, beautiful auditorium and learn a little about the theatre’s fascinating history.
Museum Campus
One thing I really like about Chicago is how many attractions are grouped together, making sightseeing much easier. Museum Campus is a perfect example. Sitting right beside Lake Michigan, it’s home to three of the city’s biggest museums.
The Shedd Aquarium houses thousands of marine animals, including sharks, beluga whales and sea otters. Right next door, the Field Museum is famous for Sue, the largest and most complete Tyrannosaurus rex fossil ever discovered. You’ll also find Adler Planetarium here, America’s first planetarium, where interactive exhibits are paired with some of the best skyline views in the city.
Even if you don’t have time to visit all three museums, the lakeside walking paths alone make this area well worth exploring.
Wrigley Field
You don’t have to be a baseball fan to appreciate Wrigley Field. Home to the Chicago Cubs since 1916, it’s one of the oldest baseball stadiums in the United States and has so much character. The ivy-covered outfield walls, old-fashioned scoreboard and traditional grandstands make it feel completely different from modern sports stadiums.
If you’re lucky enough to be visiting during baseball season, I’d definitely recommend catching a Cubs game. Even if you don’t understand every rule, the atmosphere is all part of the experience.
If there’s no game on, you can still join a guided tour to explore behind the scenes and learn more about the stadium’s history.
Why Chicago Should Be on Your Travel List
Before I arrived, I honestly wasn’t sure what Chicago would be like. I left wondering why I’d waited so long to visit.
What surprised me most wasn’t just the architecture or the skyline, but how easy the city was to explore and how welcoming it felt. I loved being able to walk between so many attractions, stop for a coffee along the Riverwalk, spend time in beautiful green spaces and discover little corners of the city without feeling rushed. If you’re planning your first trip, these places to visit in Chicago offer a fantastic introduction to everything the city has to offer.
And if you’re looking for more things to do in Chicago, hotel recommendations and travel tips, be sure to explore the rest of the Travel For Phoebe blog. You can also join me on YouTube, where I share my favourite travel experiences, honest travel advice and plenty of practical tips to help you make the most of your next adventure.