Touring Chicago On Foot: The Loop

Chicago: A Tourist Favorite

Earlier this year TripAdvisor named Chicago the 4th most popular tourist destination in the US. Their review of the city says that it is a “…cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans.” It’s friendly and accessible to all types of visitors: those from the US or from other countries, solo travelers, couples or families. A visitor or resident could spend months or even years exploring all of Chicago’s 77 distinct communities. Touring Chicago on foot is easy, inexpensive and fun!

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 guide to touring Chicago on foot will provide you with some insight and images from some of my favorite spots in the area.

Touring 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 see only one community while touring Chicago on foot, 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.

By the way – there are many more exciting and interesting ways to see Chicago. If you want to learn more, check out 8 Ways To Rock Chicago Solo Style from the guys over at!

touring Chicago on foot
Sunset on the Chicago River from London House

The Chicago River

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.


Millennium Park

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. One of the nice things about touring Chicago on foot is that you can experience beautiful places like the Park that aren’t directly accessible to vehicular traffic.

At Millennium Park 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.

touring Chicago on foot
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.

Towards the east side of Pritzker Pavilion, you’ll see a foot bridge that takes you over Columbus Drive and to a newer extension of the Millennium Park area. The BP Pedestrian Bridge is a work of art in itself – it snakes back and forth and creates an interesting visual. The sides of the bridge are also cladded with stainless steel which captures and reflects sunlight, and images from the buildings around it. Following the bridge east takes you directly to Maggie Daley Park.

Maggie Daley Park

Maggie Daley Park is the newest part of the Millennium Park campus. The park is named for the Maggie Daley, the late wife of former Chicago mayor Richard M. Daley. Mrs. Daley passed away in 2011, and the park named in her honor was opened in 2014. It features gardens and a walking trail, along with a dual-purpose area near the middle: a track for rollerblading in the summer and skating in the winter. In the middle of the track is a large 2-story wall which is used for climbing during the summer months.

While you’re walking around the Park, don’t forget to look back west – you’ll see some amazing views of the skyscrapers in the Loop area.

The Art Institute of Chicago

You could probably spend an entire day just visiting the Art Institute of Chicago alone. Since its humble beginnings in 1879, the Art Institute of Chicago has become one of the largest art museums in the world. It contains over 300,000 works of art – from paintings to sculpture to glass…and so much more. The museum’s Modern Art Wing opened in 2009, increasing the overall size of the Art Institute to over 1,000,000 square feet (93,000 sq m).

The Institute also hosts periodic special exhibitions and retrospectives of famous artists. In the past I’ve seen exhibitions of art from Monet, Van Gogh, Edward Hopper, and many more. If you live in Illinois, you’re lucky (at least in one aspect) – the Institute has free admission for Illinois residents on Thursdays from 5P-8P (see their website for more information on admission prices and free admission policies). If you’re not from Illinois, expect that the admission might be a bit on the expensive side. One of the best ways to save on admission the the Art Institute and other museums and attractions is the Chicago Explorer Pass. It gives you discounted, fast-pass entry to 25 Chicago attractions, and is good for up to 30 days.

Buckingham Fountain

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. You’ll see lots of other fellow tourists here touring Chicago on foot, bicycle, Segway and skateboards – it’s a popular place for non-vehicular traffic.

touring Chicago on foot
Buckingham Fountain

Enjoying Chicago’s Memorable Foods

After all the energy you expended touring Chicago on foot, you likely worked up an appetite! Sure, you can find chain restaurants like Starbucks, Subway, or Corner Bakery…but let’s be honest, none of those are unique Chicago institutions. Chicago is most famous for three types of food, two of which were invented here:

Deep Dish Pizza

Although pizza itself didn’t originate in Chicago, it’s generally accepted that we are the home of deep-dish style pizza, also sometimes called “Chicago-style pizza.” It’s baked in a pan that is typically 2-3″ deep, and unless you have a monster appetite one or two slices should do you. There are lots of debates about who makes the best deep-dish in Chicago, and it all comes down to personal preference. Gino’s East restaurants make a darned good pizza, and dining at the original store on Rush Street is a really fun experience. Travel blogger Katie O’Donoghue wrote about her first time experience eating at Gino’s East…her post on it will make your mouth water!

Italian Beef Sandwiches

Italian Beef Sandwiches also originated in Chicago, probably around the 1930s. The sandwich is made up of long, thin slices of beef that have been simmered in au jus and spices for several hours. The meat is served on an Italian-style roll and is usually topped with sweet or hot peppers. When you order your sandwich, you just order it “with” or “without” (or as a Chicagoan would say, “wit” or “widdout”) to indicate whether you want peppers. You can also order it dry, wet or dunked – depending on if you want it without au jus (“gravy”, as Chicagoans call it), wet (meaning with extra gravy), or dunked (the entire sandwich is submerged in the au jus), as is your preference. There are probably 30 or more chains restaurants that serve Italian beef – my personal favorite in the city is Al’s Beef, and for the suburbs it’s Portillo’s.

Hot Dogs

Of the top three foods most associated with Chicago, the hot dog is the only one that didn’t originate here. It, along with the Italian beef sandwich, are pretty easy to eat while you’re out and about touring Chicago on foot…you don’t need to stop and sit down to enjoy a Chicago dog.

A true Chicago-style hot dog is a culinary masterpiece with a very specific recipe. Vary from the recipe, and it’s not a true Chicago dog. A Chicago dog is usually boiled, then served on a poppy-seed bun and served with the following:

  • Yellow mustard
  • Chopped white onions
  • Pickle relish
  • Dill pickle spear
  • Tomatoes (either slices or wedges)
  • Sweet peppers
  • Celery salt

That’s it. Nothing else – and ESPECIALLY no catsup on it. For the love of all that is holy, when you’re in Chicago just don’t put catsup on your hot dog, under any circumstances. It’s just not done. If someone does this, they might as well slap a big “I’m a tourist!” label on their forehead. Leave it off…trust me, you’ll enjoy the dog more and you’ll blend in better.

One last thought on Chicago’s food options – website offers an experience called Secret Food Tours Chicago
which allows you to experience some of our unique foods and restaurants in a special and memorable way.

Wrapping It All Up

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!




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