10 Jan 2022 Travel Inspirations

Top Things to Do and See in Chicago

A visit to the Windy City lets you experience somewhere that takes on a whole life of its own and offers an alternative to New York. From stunning art deco architecture to top-notch cuisine, Chicago is a place filled with fun things to do, see and eat. Whether you’re looking to take in the local culture, experience the nightlife or sample a little bit of everything, we’ve put this guide together featuring the very best of this Midwestern metropolis.

Visit Millennium Park ⛲

Millennium Park

You will find Millennium Park along Lake Michigan with its scenic green space showcasing cutting-edge art, architecture and landscaping. It’s probably the most well-known park in Chicago after opening for the millennium some twenty-odd years ago. Plenty of events take place here throughout the year, but you can also enjoy a leisurely stroll around the park. The Crown Fountain, Great Lawn and Jay Pritzker Pavilion and Cloud Gate are some landmarks worth looking out for.

The Magnificent Mile 🛍️

The Magnificent Mile

The Magnificent Mile is a portion of Michigan Avenue stretching between Lake Shore Drive and the Chicago River. It’s a place to shop ‘til you drop, thanks to the many luxury department stores and retailers that line the streets. Once you’ve finished doing a spot of shopping, head to one of the classy restaurants and enjoy a five-star meal to cap off your day.

Chicago pizza tours 🍕

Chicago pizza tours

Pizza is The Windy City’s most famous culinary export, and there are plenty of tours available where you can learn all about the makings of a tasty Chi-Town slice. Go on adventures focused on food with plenty of sampling opportunities and enjoy tours that really go all out, including options that offer guests extravagant transport in the form of a limousine ride. So if you’ve never tasted pizza in a limousine, now’s your chance.

Art Institute of Chicago 🖼️

Art Institute of Chicago

Discover a permanent selection of 300,000 artworks at the Art Institute of Chicago. Guarded by an iconic pair of bronze lions, the institute is filled to the brim with masterpieces from all eras. You’ll find Andy Warhol prints, as well as Georges Seurat’s A Sunday on La Grande Jatte painting, which is famous for its appearance in Ferris Bueller’s Day Off. There are also various exhibitions showcasing everything from conceptual art to abstract pieces throughout the year.

Navy Pier 🛥️

Navy Pier

Spend a day at Navy Pier and make sure you go for a ride on the Ferris wheel, which stands at an impressive 196 feet tall. There’s also an 18-hole miniature golf course where you can practice your putting, as well as the Chicago Shakespeare Theatre and the Miller Lite Beer Garden. You’ll find concerts aplenty during the summer months and some spectacular fireworks displays on New Year’s Eve.

Bloomingdale Trail (The 606) 🌳

Bloomingdale Trail (The 606)

The Bloomingdale Trail is Chicago’s answer to New York’s High Line. Also known as The 606, it’s a three-mile walk on an elevated greenway running west and east on the city’s North Side. The formerly abandoned rail line has everything from public art installations to gardens and is a great way to experience part of the city on foot.

360 Chicago 🌌

360 Chicago

Formerly known as the John Hancock Center, 360 Chicago is an observatory offering views of the city and surrounding states. It stands 1,030 feet above street level and provides spectacular sights from the 94th floor that are hard to beat. Once you’re done gazing at the stars and beyond, stop by 360 CHICAGO, a stylish bar serving up a cocktail or two. Then explore some of the interactive exhibits detailing the city’s rich history.

Chicago Architecture River Cruise 🌇

Chicago Architecture River Cruise

Chicago’s architecture is some of the most eye-catching in the United States, which is why you should see it from the best vantage points, such as a river cruise. Not only will you see the spectacular buildings, but you’ll also learn about the history of iconic structures like the Wrigley Building, the Leo Burnett Building and the Fulton house. Just make sure you’ve got a camera at the ready to capture all of those skyline photo opportunities.

Bordel 🍹


Embrace the lively nightlife scene in Chicago with a visit to Bordel. This Parisian-inspired speakeasy offers a moody ambience and snazzy cocktails while paying homage to the city’s past. From crimson couches to velvet dining and burlesque dancing, Bordel has a bit of everything to ensure you enjoy a night out in Chicago in style.

Head to Chinatown 🥡

Head to Chinatown

Chinatown is filled with delicious restaurants, shops and nods to East Asian architecture everywhere you look. It’s ideal for a stroll out and about while you take time to wander between shops before stopping at one of the authentic eateries for a delicious bite to eat. Make sure you order some dumplings and Peking duck before continuing your journey through Chinatown.

The best places to visit in Chicago

There’s so much to do and see in Chicago, whether you’re a first-time visitor or have been multiple times before. So make your next trip to the US a windy one with a visit to Chi-Town and take in the sights, eat delicious food and soak up the culture in the city.