Chicago is a beautiful city with skyscrapers, amazing architecture, world class museums, beautiful parks and food from around the world for you to immerse in when you visit. It is the third most populous city in the United States and is situated on a huge lakefront, on the southwestern shores of Lake Michigan. Lake Michigan is so huge that it feels like an ocean rather than a lake because you cannot see the other side. Route 66 begins (or ends) at Grant Park, Chicago.

Absolutely beautiful! Cannot see the other side! View from Oak Street Beach
Absolutely beautiful! Cannot see the other side! View from Oak Street Beach

My top picks for Chicago are:

  1. The Lakefront

Is one of my favourite parts of Chicago. It is perfect for a morning jog or cycling, play beach volleyball and you can even go rollerblading. When the sunsets, its perfect to walk along the shores and get your feet into the cool water. It is absolutely beautiful when you see the sun just setting behind the skyscrapers and glimpses of sunlight coming through in between the buildings. In the summer months, the shores come alive with activities and music and food.

Sunset over the skyscrapers
Sunset over the skyscrapers
  1. The Riverwalk

The Chicago Riverwalk is a beautiful pedestrian walkway along the Chicago River, spanning from Lake Shore Drive to Franklin Street. You will enjoy the many showcase of art, restaurants and bars where you can stop and enjoy a pint or two and resume sightseeing.

Spoilt with skyscrapers and architectural design during a Riverwalk
Spoilt with skyscrapers and architectural design during a Riverwalk
  1. Shop till you drop! Michigan Avenue or as it’s often referred to as the Magnificent Mile is a mile-long street of shops and is the most popular shopping street in Chicago, just like 5th Avenue is in New York! At the north end of Michigan Avenue is Oak Street, where you will find designer and luxury goods and high-end brand names such as Gucci and Prada. From the south of the River, there is State Street where you will find affordable shopping at Macy’s, and more shops such as Forever21. In winter, these shop windows sparkle with pretty Christmas decorations and in the spring/summer months, the parkways are filled with colourful blooms.
  1. The Loop is the heart of the business district and it is here that you will find the great architecture that Chicago is famous for, such as the Willis (Sears) Tower, the Cultural Centre and many more.
  1. Millennium Park is in downtown Chicago and it is here where you will find the popular Chicago Bean sculpture. It is a huge park where you can run, picnic or just hangout.
  1. The Art Institute of Chicago is home to more than 5000 years of human expression depicted in sculptures, photography and textiles representing cultures from around the world.
  1. The Navy Pier is a popular attraction. It has ferries wheel, carousel and lots of restaurants and beer gardens.
  1. Fly into O’Hare Airport! Although it is one of the busiest airport in the world, it is worth flying into at least once because it is full of colourful art and has the longest neon sculpture in the world which is amazingly beautiful.

Useful information:

Airports – There are two airports here – O’Hare International and Midway. Both are easily accessible and connected to the city by the CTA (Chicago Transit Authority).

Local transport – the transport system here is good. Take the CTA line around the Loop and change where necessary to get to your destination or further out of Chicago. It’s good to familiarise yourself with the colours, for example it is the Blue Line from O’Hare International which will extend through the Loop.

Best time to visit: May – September/October.



  1. Thank you for sharing Georgina and your photos triggered happy memories of the Windy City. To me, Chicago is a fascinating and vibrant city where there is so much to do and see. I was enchanted by its beauty, especially at night. 💛

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