Chicago Top Sights To See

Since moving away from my hometown of Chicago I find that many people ask me where to visit during their upcoming travels. This guide is meant for you all who are visiting to enjoy Chicago Top Sights!

Why visit Chicago?

There’s never a dull moment in the Windy City if you happen to visit. From the thrill of a Cubs game to the beauty of Millennium Park, each destination carries a unique charm. So, read on as I share some of Chicago top sights to see through these iconic Chicago gems and for more Chicago recommendations, check out more reading below!

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The Art Institute

The Art Institute of Chicago is a treasure to the city that celebrates human creativity. It’s not only one of the oldest and largest art museums in the world, but its a space that invites reflection and wonder. I’ve been visiting here since I was a child and have very fond memories of taking in the large lions that welcome you as you arrive to the Museum. It’s truly a fabulous museum that any art or culture lover must see when visiting Chicago.

Chicago Top Sights
The Bean at Millennium Park

The Bean at Millennium Park is sometimes known as one of the most popular top Chicago sights, with its cool, warped reflections has become a symbol of Chicago’s artistic footprint. Located right by the Magnificent Mile and steps from the Art Institute, it’s the perfect spot to visit before or after a day of shopping. However, if you want to avoid crowds, I recommend going really early or later in the afternoon.

Chicago Top Sights
Chicago River Architecture Tour

Every boat ride along the Chicago River during the architectural tour is visually striking. Each skyscraper tells a story, a real testament to the innovation and creativity that define Chicago’s architectural past and present. Don’t forget to bring your camera, the sights are truly spectacular.

This is one of my FAVORITE activities to take visitors on as I enjoy it each and every time and it’s beyond gorgeous and interesting to learn the rich history of Chicago including the historic Chicago fire in 1871.

Chicago Top Sights
A Cubs Game and the Unmissable Chicago Hot Dog

There’s something electric about a Cubs game – the cheers, the friendship, and the sense of unity. My family has been going since I was a kid annually so ever since moving away I’ve looked forward to my visits home taking in a Cubs game. I even remember the Harry Carey days singing take me out to the ball game.

Every time I step into Wrigley Field, I can’t help but be swept up in the energy of the crowd. And what’s a game without a classic Chicago hot dog? Take a bite, feel the thrill, and don’t EVER put ketchup on it.

Chicago Top Sights
Chicago Top Sights

Enjoying a Cubs game with my niece Libby.

Chicago Top Sights

Finally getting to enjoy the Cubs bleacher experience for my friend Katherine’s bachelorette party. What a blast everyone needs to experience the Chicago Cubs bleachers at least once!

Fulton Market

In Fulton Market, the culinary scene comes to life on every corner. Each restaurant is a testament to Chicago’s diverse and innovative food scene. Here you’ll find lively breweries, cafes, and top-rated restaurants in a very, hip industrial vibe.

Lincoln Park Zoo

In the middle of such a busy city, Lincoln Park Zoo is a place of tranquility. Walking through its pathways, you’re able to enjoy a peaceful break from the city and enjoy time with animals and nature. I’ve been visiting the Lincoln Park Zo since I was a kid and one of my favorite memories is going to visit during the Holiday time when it’s all lit up with festive holiday lights. Oh Chicago I LOVE YOU!

Chicago Top Sights
A Night in River North

Over the years, River North’s dining scene has boomed spectacularly. A perfect night in this neighborhood will have you traveling from one remarkable restaurant to another. Most likely ending at one if its many, MANY bars or nightclubs. A night here is truly as fun as it is delicious. Read about one of my favorites, Tanta in River North here.

Chicago Top Sights
The Best Rooftop Bars in Chicago

There’s magic in enjoying a drink while overlooking Chicago’s stunning skyline whether you take in Lake Michigan, the Chicago River or just the skyline you can’t go wrong.

Rooftop bars offer a view that’s both breathtaking and intimate. Perfect for a night with friends or a date. Over the years I’ve been able to document some of my favorites and you can read them here, The Best Rooftops in Chicago to Experience.

Chicago Top Sights
The Magnificent Mile

The allure of Michigan Avenue is irresistible, a shopper’s paradise where every store is a temptation. When you visit, you’ll be amazed at the sheer diversity of Chicago’s offerings – from luxury boutiques to charming finds. Be sure to hit up 900 North Michigan Avenue my favorite mall with a Bloomingdale’s (my former employer for 10 years in New York) and other amazing stores.

Chicago Top Sights
Navy Pier

Navy Pier, though often considered touristy, holds a classic charm that’s impossible to resist. Also, for visitors, it’s usually one of the first Chicago sights they want to see. It’s a place where the nostalgia of carnival rides meets restaurants and souvenirs. With great views of Lake Michigan, this is the perfect family activity.

Pilsen’s Artistic Culinary Scene

Pilsen is truly the hub of creativity, where art and culinary delights fuse together to celebrate culture. Exploring its streets results in stumbling on all kinds of international restaurants and street art. It’s a reminder of the diversity that shapes the city.

The Skydeck at the John Hancock Building

The Skydeck at the John Hancock Building offers a vantage point that’s as exhilarating as it is humbling. Once you get to the top you’ll literally be standing among the clouds. And this is definitely not for the faint of heart, but an excellent activity for the whole family. Just be sure to check the weather and make sure it’s not too cloudy!

My locals tip is grab a hot chocolate across the street at Ghirardelli Chocolate and take it up to enjoy the view. We did this growing up as well and it’s always a super fun activity for locals and tourists.

The Signature Room at 95th in The John Hancock Building

The Signature room at the 95th is perfect for a celebration or if you’re in the mood for a once-in-a-lifetime dinner. Because of it’s location, you’ll be graced with panoramic views and a delicious menu. It’s the perfect spot to grab a martini with some oysters and enjoy the views they have to offer.

West Loop

The West Loop is a haven of sophistication and style, this is where you can find exclusive boutiques and dining establishments. Fun fact: This neighborhood has more restaurants run by former Top Chef contestants than any other neighborhood in Chicago. For my recommendations, check out Chicago’s West Loop Top 10 Restaurants List

Wicker Park

Wicker Park is one of the top sights in Chicago that is also a celebration of creativity, it is a neighborhood that thrives on art, culture, and individuality. Because of this, its vibrant streets house galleries, speakeasies, micro-breweries, and so much more. Whether it’s late-night tacos or a 4am bar, this is the place to spend a great night out.

Select photos courtesy of Unsplash &

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