Chicago —6 landmarks you can’t miss in your windy city weekend getaway.

Chicago exudes an effortlessly cool vibe, the perfect blend of a little bit of edge with a whole lot of style and elegance. Its sleek towering skyline can be seen from any angle of the city and it includes some famous architectural masterpieces like the modern Willis Tower and John Hancock Center, as well as the Tribune Tower with its gothic design.

Artsy neighborhoods, deep-dish pizza, an outstanding music scene, well designed urban outdoor spaces and walks along the lakeshore —these are just some of the few things that make the windy city unforgettable. Whether you are exploring art, savoring delicious foods, attending a festival or just soaking up the feel-good atmosphere, Chi-town has something for every kind of adventurer.

Here is quick guide of 6 must-dos while visiting this vibrant city in a stretch:

The Bean

Located in Millennium Park —the heart of downtown—and officially called Cloud Gate, this stainless steel sculpture is definitely an iconic landmark of the city and a must see while in Chicago. The curvy mirror-like surface offers a great reflection of the skyline and the surroundings of the park, if you are planning to visit the spot and snap some pics you probably want to setup your alarm early. The park gets packed fast, especially during the day, as tourists and locals alike flock to take in the sight and just enjoy the area. The park itself is home to other famous landmarks like the Jay Pritzker Pavilion where you can catch live music shows, the Crown Fountain featuring two 50-foot glass towers that display video projections of local Chicagoans' faces, which occasionally "spit" water into the reflecting pool below, and the Lurie Garden, a peaceful space with beautiful plants and flowers. It’s perfect for a stroll or a moment of relaxation amidst the bustling city. 

Millennium Park is also directly connected to Grant Park where you can see the Buckingham Fountain and visit an exhibition at The Art Institute of Chicago. Both are great spaces with views, seating areas, street vendors, art installations and seasonal events.

Pro tip: for a remarkable view of the Bean, the Park, skyline and beautiful sunset over the Lake visit Cindy’s Rooftop at the 13th floor of the Athletic Association hotel. It is usually pretty busy but you can make reservations for dinner or just swing by for a delightful cocktail.

The Magnificent Mile

Just a few steps away from Millennium Park the Magnificent Mile is famous for its upscale shopping. International stores like Zara, Topshop and H&M are lined up with luxury stores, high-end boutiques, and department stores like Nordstrom and Neiman Marcus, as well as iconic brands like Gucci and Louis Vuitton. It's definitely a shopper’s paradise as you can find everything and anything you would need here. But, it's not all about retail therapy, the street is also home to important landmarks such as the John Hancock Center (now called 360 Chicago), which offers panoramic views of the city. You can also find great cafes, art galleries, dining and entertainment. There are plenty of great dining options, from casual bites to Michelin-starred restaurants. The area is also considered a cultural hub, and home to the Museum of Contemporary Art where you can admire the work of Andy Warhol and Yayoi Kusama, among other famous artists.

In this area you will also find a variety of luxury 5-star hotels like Park Hyatt, Four Seasons and Ritz Carlton. So if this is your vibe, you will be staying right in the middle where everything happens.

Willis Tower

Now, I am not a fan of heights, but I never let fear take away from my view experiences, specially since this is one of my favorite parts when visiting a city. I love the skyline, the lights, and the aerial-like moments.

The Willis Tower is located 233 South Walker Drive, it was formerly known as the Sears Tower and it is the second tallest building in the American Continent (first One World Trade Center in New York) and has a total of 110 floors. The building is used mostly as modern office space, parking garages, retail and dining. Its highlight really is the Skydeck in the 103th floor, open to the public and offers 360 views of Chicago. And though the experience is not for the faint of heart, it is definitely a unique and not to miss event. I am talking about The Ledge, a glass floor balcony that extends out of the building providing an exhilarating view straight down to the streets of Chicago. For sure a classic, heart-pounding Chicago skyline moment.

The Skydeck is also a museum offering all of the history, architectural and engeenering details of the building. As well as the showcase of some notable characters from the city like Oprah Winfrey, Barack Obama, Louis Armstrong and Michael Jordan.

For a seamless visit, you must purchase tickets in advance and schedule your time. In general, tickets per adult go around $30-$50 USD.

The Riverwalk

The Chicago Riverwalk is a vibrant, scenic pedestrian path that stretches along the Chicago River in the heart of downtown. It’s one of the city's most popular outdoor spaces, offering a unique blend of urban beauty and relaxation. The walkway itself features a variety of attractions, including cafes, bars, and restaurants, many of which offer outdoor seating right by the water, making it a perfect place to grab a drink, enjoy a meal, or just take in the view. There are also boats or kayaks that you can rent to enjoy the city from a water perspective.

After my walk, getting into the sunset, I headed to the London House to visit their hotel rooftop located in the 22nd floor to enjoy drinks and take in the beautiful views. Situated right by the river, it’s the perfect way to end the day, offering sweeping panoramic vistas of the stunning skyline, Marina Towers and the Chicago River below. Sipping on a delicious original cocktail from their rooftop bar, seeing the city change its landscape to twinkling lights, I couldn’t help but feel completely immersed in the moment.

The Chicago Theatre

The theatre is one of the cities most renowned icons with its classic lit up sign right above State Street. Just a couple blocks from the Magnificent Mile, the theatre has stunning architecture, opulent interior and a rich history as the stage of countless performances since its opening in 1921. Today, it is still an important venue and holds major events in the city —B-52s were actually playing on close dates during my visit. Beetlejuice and the Beauty and the Beast musicals are showcasing at the moment. You can also take a tour of the venue purchasing tickets in advance and for specific times of the day, per adult you can expect to pay around $40-$50 USD. Seeing a show, taking a tour, or simply admiring the architecture, either way, the Chicago Theatre is a must-visit for anyone exploring the city's vibrant arts scene and iconic landmarks.

Navy Pier

Navy Pier is one of Chicago's most famous and bustling destinations. It is packed with attractions, restaurants, shops, and entertainment options. One of its standout features is the Centennial Wheel, a ferris wheel that provides stunning views of the city, Lake Michigan, and beyond. Navy Pier also has gardens, picnic areas, and a boardwalk that allows you to relax and enjoy the waterfront scenery. A great place to relax, hangout, and grab a cold one at one of the many bars or outdoor patios, like The Miller Lite Beer Garden, where you can listen to live music. For a more sophisticated ambiance you can visit Offshore Chicago a rooftop bar offering premium food & drinks. A fun fact of this spot is that it actually holds the world Guinness record as the largest rooftop in the world. Needless to say it offers unmatched views of the city and Lake Michigan.

Music Festival Bonus: Riot Fest

This time , I was actually in the city for a music festival —the Riot Fest—it is one of Chicago's most popular and unique music festivals, known for its mix of punk rock, alternative, and indie music, along with an overall carnival-like atmosphere. Held every year in Douglass Park, bringing music fans from all over the world. I was here to see Jimmy Eat World, Coolio, Ice Cube, Yeah Yeah Yeahs and an all time favorite headliner Nine Inch Nails.

As always it was a mind blowing experience, if you're a fan of alternative music and want to experience Chicago in a truly wild, high-energy way, this is a must-attend event that captures the rebellious spirit of the city.

I have always associated Chicago with music. In 2011, I was here for the first time to see Roger Waters: The Wall, in a performance that I thought at the time was going to be my only chance to experience something as close as I could to Pink Floyd. Fortunately, that wasn’t the case, as we all know Roger Waters —and even David Gilmour— have done several world tours after that. Still, it was a very special event in my life, one that I will never forget. It was held in the United Center, the Chicago Bulls stadium which made it even more memorable. As a millennial, I dare to say that in the 90s NBA stars were a different breed —world renowned celebrities, that even now younger generations still recognize. The Chicago Bulls ruled the world back then and with that in mind, it felt great to be in their home.

Later, I returned for another festival where I had the chance to see two big names in my list: Deftones and Alice In Chains. This is possibly the best concert I have ever attended in my life —more than a concert it really felt like a huge party where they were performing. The venue was also spectacular and located near the lake.

As if it were impossible to top any of those performances, the opportunity to see Faith No More in the Aragon Ballroom also came up a few years later.

Other major festivals like Lollapalooza which features rock, indie and pop bands or the Spring Awakening Music Festival which highlights electronic music, take place every year in Chicago, making it one of my top destinations for music events.

Know before you go.

• Getting into the city: if you don’t have a lot of luggage and are ready to embrace the local experience, skip the Uber or taxi and take the train instead, it travels throughout the city and the difference in pricing is significant —around $50 for an Uber versus $5 in a train or even less.

• I stayed at the Hyatt Regency McCormick in an upgraded room with incredible views of the city (photo above). While it may not be the closest hotel to the sightseeing areas, it can be a nice place to retreat from the hustle and bustle of everyday, also is close to the water and amenities are top-notch. Rates are around $300 USD.

• Chicago is famous for its deep-dish pizza —a symbol of its culinary identity. Try Pizzeria Uno at 29 E Ohio Street, the birthplace of this iconic dish since 1943.