Top Chicago Attractions You Can’t Miss

Planning a trip to the Windy City and looking for Chicago attractions? I’ve got you covered.

I LOVE Chicago, whether it’s your first time or your fiftieth, you never run out of things to do.

From iconic architecture and world-class museums to deep dish pizza and riverfront views, there’s something for every kind of traveler.

Here’s my guide to the top Chicago attractions you can’t miss, including a few personal favourites and handy tips along the way.

So grab a drink, find a comfy chair and let me walk you through all Chicago has to offer.

Top Chicago Attractions You Can’t Miss

The World’s Largest Starbucks (Starbucks Reserve Roastery)

Located on Michigan Avenue, this five-story coffee wonderland is more than just a place to grab a latte.

You can watch beans being roasted right in front of you, try coffee-inspired cocktails at the bar, or sample rare international blends you won’t find at your local Starbucks.

It feels more like a coffee museum-meets-luxury lounge than a café.

Even if you’re not a huge coffee fan, the vibe alone is worth experiencing.

The architecture is sleek and modern, and the views from the upper levels overlook the bustling Magnificent Mile.

This is definitely a place you want to check out as it’s quite unique and a great place for that perfect photo. This is one of the top Chicago attractions.

First time in Chicago? Read my tips here: Traveling to Chicago: What You Really Need to Know Before You Go

Walk The Chicago Riverwalk

The Riverwalk is one of my favourite places in the city. Winding along the south bank of the Chicago River, it offers a completely different perspective of downtown.

You can stroll beside the water, stop at little cafés or wine bars, or sit on the steps and watch boats glide by under historic bridges.

If you love people watching, like me, this place is heaven.

On sunny days, the path it’s just perfect and the views of the iconic skyscrapers are always wonderful.

It’s especially magical in the early evening when the golden hour lights up the water and buildings.

This is one of Chicago’s tourist attractions you won’t want to miss.

Wander Around The Art Institute of Chicago

Home to one of the best art collections in the world, the Art Institute of Chicago is a treasure trove for art lovers.

Walking through its galleries is like traveling through time and across cultures. You’ll find everything from ancient artefacts to modern masterpieces.

The Impressionist collection is world-renowned.

Standing in front of Grant Wood’s “American Gothic” or Georges Seurat’s “A Sunday on La Grande Jatte” are unforgettable moments.

I love this place and can happily spend all day here.

My advice is to book your ticket before you go to save money and avoid waiting in line, as this is an extremely popular Chicago attraction.

Book Your Ticket Here: The Art Institute of Chicago

Take A Photo At The Bean (aka Cloud Gate)

Officially called Cloud Gate, this polished steel sculpture affectionately known as “The Bean” is located in the centre of Millennium Park.

It reflects both the skyline and the people standing beneath it, making it one of the most photographed spots in the city.

Come early in the morning or later in the evening if you want to avoid the crowds.

It can get really busy here, and we all know a photo is best with only you in it.

Book Tickets Here: Chicago: Instagram Tour of the Most Famous Spots?

See The Sights On An Architectural River Cruise

This is hands down one of the most fun Chicago attractions. And one I have personally done multiple times!

Even if you’ve been to the city before, the river cruise gives you a whole new appreciation for its history and design.

While relaxing knowledgeable guides share the stories behind the buildings and you get an unimpeded view of all the iconic spots.

Many cruises depart from along the Riverwalk. In my opinion, this is one of the best Chicago attractions.

Book River Cruise Tickets Here: Architectural River Cruise now

Chicago Attractions: Have Fun At Navy Pier

Navy Pier stretches out into Lake Michigan and is packed with things to do.

From restaurants and shops to the Centennial Wheel, which offers fantastic views over the lake and city skyline, there are so many Chicago attractions here!

In summer, you might catch live music, festivals, and even fireworks.

While it can feel touristy, it’s worth a visit for the sheer variety of experiences.

This is one of the top Chicago attractions for families or anyone who wants to enjoy classic lakefront fun.

There is also one of the best rooftop bars in Chicago which is a wonderful place to soak up the atmosphere.

One of the fun Chicago attractions.

Book Tickets Here: Chicago: Navy Pier Centennial Wheel Ticket

Enjoy The View From Willis Tower Skydeck And The Ledge

The Willis Tower, formerly known as the Sears Tower, is one of the tallest buildings in the Western Hemisphere.

If you are good with heights, then a trip here is a must.

Head up to the 103rd floor Skydeck, and you’ll find yourself stepping out onto The Ledge.

It is a glass box that extends four feet out from the building.

Standing on it is nerve-wracking and thrilling at the same time.

On clear days, you can see four states from the top. This is not one if you are afraid of heights.

Book Tickets Here: Skydeck The Ledge timed ticket

Chicago Attractions: Try Some Deep Dish Pizza

Chicago and deep dish go hand in hand. And who doesn’t love a deep dish?

The buttery crust, the gooey cheese, the thick, tangy tomato sauce layered on top, heaven!

There are debates over who makes the best one, but you can’t go wrong with Giordano’s, Lou Malnati’s, or Pequod’s.

Each has its own twist, so if you’re staying a few days, try more than one and pick your favourite.

Be prepared for a wait, though; these places are popular for a reason.

Read next: 15 Places To Get The Best Pizza In Chicago

Watch Some Professional Sports

If you’re a sports fan, Chicago is a dream city. Depending on the season, you can watch the Cubs play at historic Wrigley Field in the summer,

Catch a Bears game at Soldier Field in the fall, or see the Bulls or Blackhawks take the court and ice at United Center in the winter.

Even if you’re not usually into sports, the atmosphere is electric.

Wrigleyville, in particular, comes alive on game days and is full of bars, music, and celebration.

Honestly trust me you will have fun even if you are not a sports fan. And you can always just get a tour of the stadium if you really don’t want to watcha game.

Chicago Attractions: Marvel At The Chicago Cultural Center

If you’re into architecture, hidden gems, or just love beautiful spaces, don’t miss the Chicago Cultural Center.

It’s completely free to enter, and honestly, it’s one of the most stunning buildings in the city.

The highlight is the massive Tiffany stained-glass dome, the largest of its kind in the world, but there’s also a second dome in a different style, plus grand staircases, intricate mosaics, and rotating art exhibitions.

I just find this place so beautiful and fascinating. It is one of those places that locals love and it’s right in the heart of downtown, steps from Millennium Park.

I highly recommend a visit here.

Chicago Attractions: 360 Chicago Observation Deck

While most people head to the Skydeck at Willis Tower, the 360 Chicago Observation Deck offers a slightly different (and arguably better?) view, especially of Lake Michigan.

Located on the 94th floor of the former John Hancock Center, it’s less crowded than Willis Tower and includes the thrilling TILT experience, where you lean out over the city in a glass box that tilts forward.

Even if you skip TILT, the floor-to-ceiling windows give you incredible panoramic views of the skyline, lake, and shoreline.

There’s also a bar where you can sip a cocktail while watching the sun set behind the skyscrapers.

Book Tickets Here: Chicago: 360 Chicago Observation Deck General Admission

Packing List Suggestions When Visiting Chicago Attractions

No matter if you fly or drive to Chicago, read my tips on how to pack lightly in a carry-on.

This unisex RFID blocking concealed travel pouch is lightweight and comes in several colors.

These RFID Sleeves D sleeves are another perfect solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday.

It has Bluetooth connectivity and is a breeze to use for taking selfies.

I never leave home on a trip without my Bobble filtration bottle. 

The replaceable carbon filter ensures fresh water whenever you need it.

This foldable water-resistant backpack would be great.

Not all beaches are created equally and these quick dry slip-on Aqua shoes will come in handy for the beaches in Chicago.

These men’s quick-drying trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in a lot of lens colors and frame designs, and are extremely affordable too.

If you are fond of aviator-style sunglasses, these polarized aviators may interest you.

As an Amazon Associate, I earn from qualifying purchases.

Where To Stay In Chicago

If you’re visiting Chicago for the first time, staying downtown gives you the best access to most of the city’s top attractions.

Here are some of my favourite picks by location.

In the Downtown/Loop area, The Langham Chicago offers a luxury stay with beautiful river views and top-notch service.

If you want something comfortable and a bit more budget-friendly, Hotel Blake has a historic feel with modern touches.

For travellers watching their wallets, HI Chicago Hostel is a great option that doesn’t skimp on location or amenities.

Near Navy Pier and Streeterville, Loews Chicago Hotel blends upscale comfort with easy access to the lakefront and popular landmarks.

Another good choice is SpringHill Suites by Marriott Chicago Downtown, offering modern rooms with lots of space for families or longer stays.

If you’re heading to Wrigleyville, especially during baseball season, Hotel Zachary sits right across from Wrigley Field.

It has a fun, boutique vibe that’s perfect for fans wanting to stay in the heart of the action.

Need more help? Where To Stay In Chicago: Best Hotels And Areas

I do hope this list helps you make the most of your Chicago adventure.

Whether you’re snapping selfies at the Bean, soaking in the views from the Skydeck, or biting into the cheesiest deep dish slice imaginable, Chicago always finds a way to surprise and delight.

Bring your walking shoes, your camera, and your appetite, this is one city you’ll never forget. Have fun.