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Eventually, I think Chicago will be the most beautiful great city left in the world.” ―Frank Lloyd Wright

Chicago, the Windy City, the City of Big Shoulders, the Second City. No matter what you call it, there’s no denying that Chicago is one of the most vibrant, diverse, and exciting cities in the United States. Chicago-style hot dogs, Chicago-style (deep dish) pizza, Maxwell Street Polish Sausage, jazz music, blues music, 1920s gangsters, Al Capone, it’s got it all.

Nestled along the shores of Lake Michigan, it is a city that’s been shaped by its geography. From its early days as a trading post to its current status as a global hub for business, culture, and cuisine, Chicago has always been a city on the move. But it’s not just the city’s history that makes it so fascinating. Chicago is a city of neighbourhoods, each with its unique character and charm. From the hipster enclaves of Wicker Park and Logan Square to the upscale boutiques of the Magnificent Mile.

One of the things that sets Chicago apart from other American cities is its architecture. Home to some of the world’s most iconic buildings, including the Willis Tower (formerly the Sears Tower) and the John Hancock Center, Chicago is a city that’s been shaped by its architects. Towering skyscrapers aside, Chicago prides itself in being home to incredible food with several award-winning Michelin-star restaurants. As if this wasn’t enough to make you curious, the city boasts of Chicago-style pizza and hot dogs, both of which you absolutely must try. Or you might just spend hours on end in Chicago’s entertainment scene. From several live-music scenes and festivals to award-winning theatrical productions, this city will keep you wanting for more. 

But perhaps the most exciting thing about Chicago is its people. Friendly, outgoing, and passionate, Chicagoans are the heart and soul of the city. Whether you’re chatting with a stranger on the L train or cheering on the Cubs at Wrigley Field, you’re sure to feel the warmth and hospitality that’s so characteristic of this Midwestern metropolis.

There is a reason tourists throng every year to Chicago like it’s an annual ritual. This city makes them feel at home. Chicago captures the hearts of all her visitors, enveloping them in warm familiarity that keeps them coming back. I mean who doesn’t want to come back home?

As if all of the above wasn’t enough to make Chicago one of the most phenomenal places on earth, it also has an idyllic location! Situated on Lake Michigan, Chicago presents some of the best summertime experiences. The miles and miles of beaches make it ideal for any water-related activity you might be interested in. 


Chicago’s history is so fascinating because of the city’s unprecedented growth since the city was a wilderness outpost in 1833. With only a population of 350 residents, it was unimaginable that Chicago would become the towering metropolis it is today. The city began its roots on a soggy land that was a military fort which the natives called Chigagou which translates into “wild garlic place”. However, by the end of the 19th century, the desolate swamp had transformed into a city home to over 1.7 million.

The quick and sudden rise of Chicago stunned so many that it was termed a miracle by God. The city served as a signal that American expansion and progress were all but predestined. 

Best Places To Visit 

Whatever your reason for visiting this stunning city, Chicago will charm you. Just like it has done to millions who visit it every year. So when you do plan your trip, here are the best places to visit;

Chicago Theatre

The theatre scene in Chicago is not to be missed. With over 200 companies, you are spoilt for choice. If you love theatre, prepare yourself to be blown away. Did you know that every night, there are as many as 100 shows? The thriving and abundant theatre scene in Chicago rivals most of the major cities in the United States. This is the place where many productions started before moving to Broadway such as To Kill a Mockingbird, Wicked and The Devil Wears Prada. Chicago Theater is a must-visit with its diverse showings that include comedy, plays, magic and concerts. 

Buckingham Fountain

Shooting as high as 150 feet, Buckingham Fountain should be your evening destination. At night, the fountain is showered in light and offers music shows per hour. It is a beautiful sight to see and can be quite romantic as well. 

The Bean

This is one of Chicago’s iconic landmarks. The massive Cloud Gate Sculpture known as The Bean is made of 168 exceptionally polished stainless steel plates. It is incredibly reflective and offers phenomenal views of the Chicago skyline. It’s one of the places that’s free to visit so make sure to check it out. 

Lake Michigan 

The lakeside location of Chicago provides miles upon miles of shoreline. The beautiful Lake Michigan is one of the world’s largest lakes and offers trails, parks and sandy beaches for activity all summer long. You can plan a picnic, compete in volleyball tournaments or explore the water with boats.

Public Parks

“City in a Garden” has been the motto of Chicago since the 1830s. The city has strived to ensure that there is 10% of parkland within the city. One of the most notable parks is Lincoln Park which covers 7 miles of shoreline. Visit here for its popular free zoo and conservatory.

Main Attractions

Shall we take a look at what makes Chicago such a popular destination for many people? 

The Breathtaking Towering Architecture

Chicago is famous for its skyscrapers. They tower majestically and are objects of wonder. The city actually offers architectural boat tours when the weather is warm. This is the best way to tour Chicago’s incredible architecture by boat. Take in all the massive buildings rising up in the sky and in such large numbers that make the city so futuristic. 

World-Class Museums

You won’t be able to decide which museum to visit and which one to skip. That’s the dilemma Chicago will present you in your visit. You could choose The Field Museum to see the world’s largest and most complete Tyrannosaurus Rex or visit the Museum of Science and Industry to see the largest science museum in the Western Hemisphere. Or maybe go to the Chicago History Museum and learn everything you can about this magnificent city. 

Iconic Sports Teams

The world-famous Wrigley Field

Did you know that some of the most famous sports clubs in the country hail from Chicago? The Bulls, Bears, Cubs, Blackhawks and Sox are the city’s pride despite their infamous notoriety. Catch a game of any of these iconic sports teams at any of the stadiums. 

Vibrant Art Scene

The art scene in the Windy City is like no other. It caters to the tastes of all its visitors. Catch a glimpse or better yet the entire show in the galleries, museums and public spaces. In fact, the city is known to have one of the highest concentrations of iconic art pieces aside from Eifel. You can visit the Art Institute of Chicago to see Water Lilies by Monet or American Gothic by Grant Wood.

The Incredible Musical Heritage

Chicago’s history is rich in music and the city prides itself in birthing several influential styles of music. One of the most iconic roles Chicago played in music is the invention of House Music which emerged from the city in the 1980s borrowing its name from a nightclub by the name Warehouse. The annual Chosen Few Picnic and Festival, now in its 28th year celebrates this fact. The city is also home to Chicago blues and no visit would be complete without paying a visit to Kingston Mines of Buddy Guy’s Legends. It is also immersed in jazz and Andy’s Jazz Club and Restaurant and Winter’s Jazz are two of the city’s most prominent venues. The city lives and breathes its music.

Chicago, where the legacy of Blues music lives on

Where To Eat and Drink

Head over to Portillo’s for amazing Italian beef sandwiches with lots of sweet pepper and giardiniera. The other two most infamous foods in Chicago aside from Italian beef are Chicago-style hot dogs and Chicago-style pizza at Giordano’s. These are Chicago’s pride for a reason. They are unique and incredibly delicious. Chicago’s cuisine in its multicultural restaurants might just induce a food coma.

No one does drinks like Chicago, with it being home to over 60 breweries and counting. The city has Chicago Friday Night Flights which is a tour through the city that brings together local brewers for an evening of beer and bites. Here you can sample Bridgeport, Pullman and Pilsen. Or you could drop by the recently created Riverwalk event and drink up. 

24 Hours in Chicago

So you just have a day to tour Chicago? Worry not, there’s plenty to be seen and enjoyed in 24 hours in the Windy City. Start your morning with breakfast and some delicious coffee. Head over to Foxtrot for a quick sandwich and coffee to go. Try the one at Lincoln Park but if it’s too far, don’t worry there are several in the city. 

If you are near Lincoln Park, you might as well visit Lake Michigan. Enjoy the stunning shoreline and watch the beautiful blue waters reflect the clear blue skies. It’s a spectacular scene. You can rent a bike, jog or even walk since Chicago is a very walkable city but explore the miles of shoreline. This breakfast walk along the beach can take you to the Shedd Aquarium which is a must-visit destination. Be careful not to spend hours here because believe it, you will be tempted to since it is quite beautiful with lots to see. And just like that, your morning is done and by now you are probably hungry for some lunch. 

Portillo’s hot dog is not to be missed in your short visit to the city. Make your way to the heart of the city and check out the location there. After your hotdog, you might as well do some shopping because it wouldn’t be a complete visit otherwise, right? Magnificent Mile has lots of restaurants, bars and places for sightseeing but above all is a great shopping area. Check it out. The best thing about Magnificent Mile is that if you aren’t interested in shopping, you can pretty much do any other thing you prefer. Here you can visit the 360 Chicago on top of the John Hancock Building or explore the historic Chicago Water Tower. Remember to buy tickets in advance. 

At this point, maybe all the walking has tired you so don’t be afraid to check into an Airbnb for a quick nap before beginning your evening plans. Evening in Chicago can be a challenge when it comes to deciding where to eat. The city is chock full of incredible restaurants to check out. Girl and The Goat is famed for some of the most delicious food you’ve ever had. Stephanie Izard opened the restaurant after winning “Top Chef” which went on to become one of Chicago’s most iconic restaurants. 

Girl and The Goat

Don’t forget to save room for dessert. Head down to Jeni’s Ice Cream which is a must-visit place in the city. You can be sure this will be some of the best ice cream you’ve ever had. Well, the night is still young so head over to some bars for drinks. Hit up Wrigleyville for a wild and crazy night if you’re up to it and head into Happy Camper, Sluggers or any other of the many bars here. 

If you prefer, check out Chicago’s comedy scene for an improv show. Head to Second City, the improv theatre for some live comedy. You can trust that the comedy there is top tier with alums like Steve Carell, Amy Poehler, Tina Fey and Stephen Colbert all hailing from here. 

There go your 24 hours in Chicago. There’s so much more you can add to your itinerary. Chicago is a city of experience so explore as much as you can but remember to enjoy the moment. 

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