My last visit to a big city was to Boston, and from there on it was all about islands like Key West, beaches of Costa Rica, and a spa retreat in San Diego. The next big city on my bucket list and my dream city list has always been Chicago. And I was in love with Chicago long before visiting the place. And my dream came true this year, and I can’t wait to dive into the best places to visit in Chicago.
I expected Chicago to be a big city full of people hustling and just never stopping, and it was that and so much more. All the best places to visit in Chicago left me surprised in the best way possible. I can guarantee that there is so much more depth to the city with art, architecture, and food, with lakefronts that really feel calming amidst the bustling city.
From Iconic landmarks to some hidden gems, this guide is not just a list of the best places to visit in Chicago but a personal experience. Let’s get into my recommendations and must-visit places to visit in Chicago –
Free places to visit in Chicago – Best places to visit
Millennium Park
Every list ever to come out about free places to visit in Chicago will always have Millennium Park listed. Of course, you get to see the Cloud Gate, popularly known as The Bean.
Pro Tip: Visit in the morning for less crowd
Lincoln Park Zoo
I didn’t expect much from this free zoo in the middle of the city, but I was especially surprised by the Lion Exhibit. It was great for free places to visit in Chicago, a sweet green spot with little ponds, walkable bridges, farms, and many animals on display.
Chicago Riverwalk
A place that quickly became my favourite spot, not that fancy, so to speak, but it has a very chill energy. You get to walk alongside the Chicago River, with a bunch of cafes and restaurants lined up. It is the perfect place to catch a sunset.
Garfield Park Conservatory
You may or may not be a plant person, but you would love to be here. It was an unforgettable visit for me. A huge glasshouse with a massive indoor plant collection. It is quite peaceful, with an incredible backdrop for pictures.
Lincoln Park
One of the largest parks in the city. This place has everything Chicago, view of Lake Michigan, walking and biking trails, and the stunning skyline.
Must places to visit in Chicago
Willis Tower Skydeck
This place was all over my Instagram, and I had to add it to my must-visit places to visit in Chicago list. On the 103rd floor of Wills Tower, you get to observe the whole city beneath you. Yes, because you get to see from the glass boxes that extend from the building.
Navy Pier
A typical tourist place that does not disappoint. For Must places to visit in Chicago, you have to visit Navy Pier, where you get to experience the shoreline views from the Ferris wheel. It is one of those places that is just as amazing, be it in the morning or the evening.
Art Institute of Chicago
If you want to slow down and just have a rest day but still not waste it doing nothing, going to an art gallery is usually a great pick. One of the oldest art museums that houses famous masterpieces from the modern to post-impressionist era.
Magnificent Mile
If you want to indulge in some retail therapy, then the Magnificent Mile is not less than magnificent. This is every shopper’s dream, so definitely one of the Must places to visit in Chicago. The city buzzes around you with restaurants and luxury design houses all around.
Cool places to visit in Chicago
Wicker Park
For all the cool people looking for fun things to do in Chicago, the good news is that this city will not disappoint. There are a bunch of cool places to visit in Chicago, and Wicker Park is one of those. It’s not just one place you could just walk into, it’s a whole neighbourhood.
The 606
This unique experience was on top priority for Cool places to visit in Chicago. This was actually an old railway track, which is now turned into a green corridor. It’s great for an outdoor walk, and you get to see a lot of locals here as well.
Fulton Market District
This place belongs to the future and definitely makes it to the Cool places to visit in Chicago.
You will get to experience city life like never before; everyone is on the move here. You will find interesting food options with trendy restaurants, bars, and rooftop spots.
Chicago Cultural Center
You get a free entry into the center, where you spot the breathtaking Tiffany glass dome. Located in the Beaux-Arts building in downtown Chicago. It’s the perfect blend of history with modern city life. You can also attend various art shows here.
Logan Square
If you want to spend some time in Chicago like the locals, then Logan Place is one of the coolest places to visit in Chicago. Known for its boulevard architecture and creative energy.
10 best places to visit in Chicago
Chinatown Chicago
If you want to experience something different, then transport yourself into a different world with these top 10 best places to visit in Chicago. Chinatown is this vibrant place where you, of course, get some amazing food with Chinese-themed decor. I recommend visiting Chinatown in the evening when it comes alive.
Promontory Point
A simple, quiet, peaceful place just nestling in the city. It’s one of those places where you get main character vibes. I found myself just staring at Lake Michigan, the panoramic skyline, and the stone steps, which are right by the water. If you want to watch the sunset but away from the crowd, then this is your place among the top 10 best places to visit in Chicago.
Pilsen
Located in the Lower West Side of Chicago, this one again is an underrated gem. Streets full of murals and art waiting to be admired. The crowd here is American-Mexican, which feels different from the typical Chicago crowd. You must try the local food here, it’s authentic and just so tasty, you would be craving it just like I was.
Andersonville
As I mentioned in the beginning, Chicago is deeply layered. From Chinese to Mexican culture, you will find it all. Heading into the 10 best places to visit in Chicago, now let’s get into the European Vibes. Andersonville is a neighborhood known for having a European touch. It has a cozy and charming feel to it.
Montrose Beach
Yes, Chicago has beaches, and this one is my favourite. Along with unbeatable skyline views, you get a white sandy area and a bird habitat. Pro Tip- This beach is dog-friendly, so all pet parents are welcome here. Spend some time here with your friends or family, chilling and enjoying the amazing views.
Museum of Contemporary Art Chicago
When it comes to Art, I like to explore everything a place has to offer. And this contemporary art museum is pretty underrated as well. With new exhibits every now and then, installations that are thought-provoking. It’s more about feeling it than just observing. Art in a new place hits different; it makes you have these core memories.
Green Mill Cocktail Lounge
Step back in time and attend a live jazz night at Green Mill Cocktail Lounge. This place has an old-school Chicago Vibe. And this is the place that will be the most memorable of the 10 best places to visit in Chicago. This iconic bar is a classic in Chicago and one of the oldest continuously operating jazz venues in the United States.
Ping Tom Memorial Park
Just tucked away in Chinatown, this waterfront beauty has something for everyone. This place has skyline views with calming waters and Open green spaces, making it a sweet picnic spot.
Chicago Magic Lounge
This place has a hidden speakeasy-style vibe. I got to attend fun Magic shows along with some classic cocktails.
Humboldt Park
Last but not least, the 10 best places to visit in Chicago are Humboldt Park. Another historical public park, it’s known for its lagoon. And here you will get to experience Puerto Rican culture and crowd.
Final thoughts
Chicago has something for everyone. I expected to get bored with all the urban activities and places of the city, but to my surprise, I was amazed every single day. The joy of discovering new, hidden spots is unbeatable. It’s like your own treasure hunt, a way of exploring the city where it’s a personal experience and not just ticking a bucket list.
FAQs
1. What is Chicago known for?
A: Chicago is known for many amazing things- Deep-dish pizza, Iconic skyline and architecture, and Lake Michigan waterfront.
2. What is the best time to visit Chicago?
A: The best months to visit Chicago are May to June and September to October.
