Chicago: A Tourist Favorite

Earlier this year TripAdvisor named Chicago the 4th most popular tourist destination in the US. Their review of the city states that it is a “…cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans.” A visitor or resident could spend months or even years exploring all of Chicago’s 77 distinct communities.

The design of major sections of Chicago based on the ideas and principles of American architect and urban planner Daniel Burnham. His design focused on making the city easy to navigate on foot – a benefit that modern tourists are still reaping today. I’m going to be writing multiple articles on some of my favorite Chicago neighborhoods – this article focuses on the area affectionately known as “The Loop“. This isn’t an exhaustive tour of The Loop, but hopefully it provides you with some insight on some of my favorite spots in the area.

Chicago on Foot: The Loop

Chicago’s Loop area (bordered in red)

Chicago’s Loop area is where you will find its essence and its heart and soul. If you only had the time to visit one community in Chicago, I would recommend this area as your best choice. The name for this community derived from a section of the city’s elevated train system (now known as “The L”) that looped around a rectangle formed by Lake Street, Wabash Ave., Van Buren Street and Wells Street to the north, south, east and west respectively. The area defined as “the Loop” expanded in the 20th century and now is bounded by the Chicago River to the north and west, Lake Michigan to the east, and Roosevelt Road to the south.

The best place to begin a tour of the Loop is along its north side. Start at the corner of Michigan Avenue and Wacker Drive. From this vantage point you’ll see the Wrigley Building and the Tribune Tower. These buildings are both technically in the River North area (the Chicago River is the dividing line between the Loop and River North), but it’s close enough that you can go take a peek at each of them. The pavement of Michigan Avenue contains brass plates marking the borders of Fort Dearborn – the trading post that became known as Chicago.

The Wrigley Building as seen from the top of the London House
The Tribune Tower. Image credit: Stuart Seeger / Flickr

Sunset on the Chicago River from London House

If you’re in need of a quick drink, something to eat, or just want to take in a great view, check out the bar and restaurant at the top of the London House. It’s a fun and hip place to experience, and you can see the Chicago River and the buildings from a completely different vantage point.

If you walk west along Wacker Drive, keep your eyes open for the Chicago Riverwalk. It’s a beautiful walking path dotted with cosy restaurants and bars and sits right on the edge of the Chicago River. If you’re into people watching or candid people photos, this is a great place to be.


Cloud Gate, a/k/a “The Bean” (from

From the area around the London House, you can head south toward Millennium Park. The Park is at the corner of Michigan Avenue and Randolph Street. Here you’ll see one of Chicago’s most famous sculpture: Cloud Gate, better known as “The Bean”. The highly reflective surface and distinct curves provide a fun-house mirror view of the buildings and landscape in the area. The view here is always beautiful regardless of time of day or season.

Jay Pritzker Pavilion at Night

Wandering eastward from The Bean takes you toward another of the city’s architectural gems, Jay Pritzker Pavilion. The pavilion, designed by famed architect Frank Gehry, hosts public concerts and other events throughout the year. The Pavilion has a large lawn and comfortable seating around it. It’s a great place for relax and think, and to take in the architecture of the downtown area.

Of course…no tour of The Loop is complete without hitting one of Chicago’s most recognizable landmarks – Buckingham Fountain. Opened in 1927, it’s one of the largest fountains in the world and serves as the centerpiece for Grant Park – just to the south of the Millennium Park area. During the season when the fountain is active, tourists and locals flock here at all hours of the day and night for iconic skyline photos.

Buckingham Fountain

I could write a book about all the places to visit in The Loop area alone…maybe some day, I will. Until then – I hope this short walking tour guide inspires you to visit my (adopted) home town and one of the greatest cities in the world!




  1. So many of these sights ive seen in movies and always wanted to get there in person! #backpackbloggers

  2. Thanks for posting! So many of these sights ive seen in movies and always wanted to get there in person! #backpackbloggers

  3. Awesome! I’m going to Chicago for the first time next week and touring by myself, so this is perfect. Thank you for giving me a plan!

    • travelstories

      Cool – glad I had good timing on my post! Hope you enjoy yourself…I’m enormously proud of my adopted home town. 🙂

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