Chicago Walking Tour (Self-Guided)

It should come as no surprise at this point that I love to walk. Lucky for me, Chicago has some amazing free walks available throughout the city. Despite all our best efforts, we hardly made a dent in my walking wish list during our brief house sit in Chicago. In order to pack in as much as possible, I created a looped, self- guided Chicago walking tour of 3.5 miles through downtown.


Jen’s Chicago Walking Tour

Chicago Riverwalk looking over one bridge towards another

Chicago Riverwalk

The Chicago Riverwalk is a 1.25 mile-long pedestrian path that runs along the Chicago River. It is the perfect downtown stroll, with views of the river, towering sky scrapers, and plenty more.

Chicago Riverwalk: 1.25 Miles of Chicago's Downtown. Part of The Places We Live's Self-Guided, Chicago Walking TourOur Chicago walking tour began at the Merchandise Mart station (#1). Also known as theMART, this building is home to a shopping center, restaurants, and a CTA L station. It’s the last one before entering The Loop, so it’s a great place to begin a walking adventure. Once out of the station, it’s a quick jaunt across the bridge to the Riverwalk. We made the mistake of going on a beautiful Saturday afternoon, so it was pretty much back-to-back pedestrian traffic on the Riverwalk. I’m talking nearly Disney World level chaos. Someone sweat on me.

Not interested in walking through the crowds? Try some of the best rooftop views instead. We’re not much for slow moving strollers and afternoon drunks (if we’re not included, that is), so we moved pretty quickly through the remaining mile of the path. The plus side is that there were amazing picture opportunities, interesting history stops, and plenty of cocktail opportunities along the way. If you’re so inclined, you could take a scenic river cruise or hop on a water taxi to get you where you want to go.

My favorite stop was near Trump Tower which, whether you like the man or not, is a lovely building. It was really fun to see the pictures that people were taking there. Some were standing proud with heart fingers and peace signs. Others were taking pictures of their friends flipping off the building or screaming at it. It was a delightful spectacle of Americans’ freedom of speech.

Jen from the Places We Live stands on the bridge at Maggie Daley Park during her self-guided, Chicago Walking Tour.

Maggie Daley Park

Maggie Daley Park is a fun urban green space near the shores of Lake Michigan. It hosts a climbing wall, large playgrounds, tennis courts, a garden, and plenty of snack shops. During the winter months, this park hosts a skating ribbon, which we didn’t get to see in use, but I can imagine how much fun it would be, and would love to come back and try it out. In general, the park looked really fun and makes for a great place to stop and hang out on our Chicago walking tour.

Jay Pritzker Pavilion viewed by The Places We Live for the Self-Guided, Chicago Walking Tour

Millennium Park

A Chicago walking tour would not be complete without a visit to Millennium Park. The park hosts the famous Cloud Gate sculpture, the Jay Pritzker Pavilion, and the annual Christmas tree lighting ceremony. Located downtown and just off the lake shore, Millennium Park is a bustling and crowded green space.

Cloud Gate, also known as The Bean, was designed by Sir Anish Kapoor. The sculpture was inspired by liquid mercury. I loved it’s reflective surface; it gave a beautiful, warped view of the city skyline and passing clouds. I was not the only one drawn to this effect, as there were crowds of people all trying to get the perfect picture with this iconic sculpture. Be prepared for slow moving foot traffic and photo bombers.

Photo by Sawyer Bengtson on Unsplash

East Lake Street

Perogie Heaven in Chicago, Illinois - The Places We LiveThe final leg of our Chicago walking tour takes us down E. Lake Street, which connects us back to our metro station and has a few notable stops along the way.

While not as scenic as the Riverwalk or parks, we had an enjoyable stroll past The Chicago Theatre, which hosts top shows in music, comedy, and fine arts. We also passed the American Writers Museum. It has a mission to “engage the public in celebrating American writers and exploring their influence on our history, our identity, our culture, and our daily lives”. I would have enjoyed visiting both, but our time was short and the sight-seeing wish list was way too long.

However, we did make a quick stop at Pierogi Heaven before returning to the train station. Neither of us had ever eaten pierogies before, and now I realize what I’ve been missing out on this whole time! The advertising was spot on: it was heavenly.

In the end, we didn’t get to see nearly enough during our short trip to Chicago. Consequently, it looks like I will have to plan another trip in the near future. I am glad, however, that I put together this Chicago walking tour that allowed us to hit most of the major stops in one fell swoop. If you are also in town for a short time, I hope it comes in handy for you as well. Enjoy!

Like it? Share it!

Self-Guided Walking Tour of Chicago, Illinois. Includes Chicago Riverwalk, Millennium Park, and The Chicago Theatre. Created by The Places We Live  Chicago Riverwalk: 1.25 Miles of Chicago's Downtown. Part of The Places We Live's Self-Guided, Chicago Walking Tour  Perogie Heaven in Chicago, Illinois - The Places We Live


Leave a Comment

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Create a website or blog at

Up ↑

%d bloggers like this: