Best 10 in Chicago not to miss

Best 10 in the beautiful City of Chicago not to miss

The best 10 in Chicago not to miss is only a short list of experiences compared to the variety of activities that one can do here. Chicago, popularly known as the Windy City although not exactly named for the weather, 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.

Chicago, Illinois

This city 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.

In addition, as I am sure most of you are familiar with Route 66, known as “America’s Highway”.  Route 66 begins (or ends, depends where you begin your journey) at Grant Park. However, for now, come along with me and discover what my top 10 are.

Best 10 on Chicago are:

1 | The Lakefront

The Lakefront is one of my favourite areas of Chicago. It is perfect for a morning jog or cycling, play beach volleyball and you can even go rollerblading.

When the sun sets, 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.

2 | 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.

3 | 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 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.

Christmas in Chicago
Chicago by Night

In winter, these shop windows sparkle with pretty Christmas decorations and in the spring/summer months, the parkways are filled with colourful blooms.

4 | The Loop in Chicago

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. The Loop is a vibrant area for eateries and theatres.

Alongside these, in a prime waterside location, there is Marina City towers in Chicago. The bottom 20 storeys of the twin towers of this iconic building consist of continuous spirals of parking and the top floors dedicated to apartments.

5 | Millennium Park

Millennium Park is in downtown Chicago and it is here where you will find the popular Chicago Bean sculpture, also known as “Cloud Gate”  by Sir Anish Kapoor It is a huge park where you can run, picnic or just hangout.

6 | The Art Institute of Chicago

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. This is definitely a “Must See” for any art or history enthusiast.

7 | The Navy Pier | Best 10 in Chicago

The Navy Pier is a popular attraction. It has ferries wheel, carousel and lots of restaurants and beer gardens. Suitable for anyone – family with children, couples, singles, young and old.

8 | Chicago’s Deep Dish Pizza

One of my favourite pizza and I am sure many of you pizza lovers out there, is the Chicago-style “deep-dish” pizza. So, when in Chicago, head over to Pizzeria Uno where this pizza was invented in 1943.

Although the pizza is known as “deep-dish”, the crust itself is thin, but deep! Of course, mine was pepperoni.

To know more of Pizzeria Uno or to make a reservation, click on the link below:

9 | Dining in Chicago | Best 10 in Chicago

Chicago is renowned for its world class cuisines, from steakhouses, Cantonese stir-fry and chicken pot pie. There are many diners and eateries around the City, from high-end dining to casual open-air experiences.

10 | Fly into O’Hare Airport

Although it is one of the busiest airports in the world, I would highly recommend that you fly into O’Hare at least once in your lifetime. Besides the crowd, and the long queues at security, you will be rewarded with one of the most colourful sight.

The colours of the neon lights in the 744-foot tunnel that connects United Airline’s Concourse B and C is an amazingly beautiful experience and for some, it may transport you back to your late teen disco days. It is full of colour and is the longest neon sculpture in the world.

This piece of art is called “The Sky’s the Limit”, by Michael Hayden. If you are interested in knowing more about this artwork, click here.

Conclusion on best 10 in Chicago

Chicago has plenty more attractions than what I have listed here. It is a City to visit and experience because of its skyscrapers, world-class food and a fun nightlife. It has something for everyone.

Travel tips on Chicago

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.

Keep exploring

Best of England UK
Italy - complete one-stop resource for travellers
Scotland - ultimate guide

Best 10 in Chicago not to miss first published at and is regularly updated. Last update September 25, 2021

Stay Connected with Timeless Travel Steps for the latest in our Travel News

*Privacy Policy

line breaker

By Georgina

Georgina is a travel writer and a content creator. An escapist, she seeks stories, off-beat things to do, and adores the beauty of culture while embracing comfort and slow travel as a responsible traveller in the off-season. Georgina has lived in 3 continents, visited 30+ countries and strives to share her travel steps, passion, and experienced tips to inspire her readers to explore for themselves. Georgina enjoys venturing solo, takes pleasure in listening to classical, country & jazz, and delights in spending joyous time with A & M, her two adult children.


  1. Chicago is indeed a lovely city to spend some time in and a stopover seems perfect. I experienced Chicago at various times over a period of four months when I was in the US, each was different and unique. There is so much more of Chicago I am yet to experience and look forward to returning.

  2. We took a train from NYC to Chicago a few years ago, and had an overnight stop in Chicago and loved the city. We didn’t do any sights we just wandered around the streets exploring the city and eating. We didn’t have a pizza though! I always thought deep dish pizza meant it had a thick crust, and I like my pizza crust really thin. So we steered clear of it. We know for next time.

  3. Ohh Chicago is pretty! Yeap, didn’t like the wind either. 🙂

  4. Oh I really needed to see this. Today it is super cold and windy in Chicago but a great reminder that the city really is so pretty!

  5. Thank you so much for your lovely comments. I am glad that my post reminded you of happy memories.

  6. 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. 💛

  7. footstepsofanolderwoman says:

    Thank you so much 🙂

Share your thoughts here...I would love to hear from you

This site uses Akismet to reduce spam. Learn how your comment data is processed.