The Chicago Loop photo by Patrick Robert Doyle -unsplash
Exploring Chicago Neighborhoods,  random adventures

exploring the chicago loop

This content contains affiliate links to products. We may receive a small commission for purchases made through these links at no cost to you. Chicago Loop photo by Patrick Robert Doyle – Unsplash

Find yourself in downtown Chicago (aka the Loop, the central business district), and you have a few hours to explore? Here’s what to go/see/do in the Chicago Loop. Make sure you read until the end for new & updated things happening in the Loop!

cultural center

First, head over to the Cultural Center, 78 E Washington St. (Washington & Michigan), across the street from Millennium Park, which happens to be my favorite building in the city. The exterior is a classic example of Beaux-Arts, a trendy, classic style (derived from the principles of Greek and Roman architecture of classical antiquity) of architecture influenced by the 1893 World’s Columbian buildings Exposition. It was built in 1897 by Shepley, Rutan & Coolidge.

An interesting book to learn about the 1893 World’s Columbian Exposition is The Devil in the White City by Erik Larson. It’s all about building the World’s Columbian Exposition, aka the White City, and murders happening simultaneously. I found it fascinating yet gruesome. It’s standard reading for those interested in Chicago history. Rumor has it that there is a movie being made, but no information on when it is due out, with Leonardo DiCaprio playing the role of the devil.

The bronze cow outside of the Cultural Center in Chicago
The bronze cow outside of the Cultural Center in Chicago

Head to the Washington Street side to check out the cow outside. Why is there a bronze cow in downtown Chicago? No, it’s not Mrs. O’Leary’s cow that allegedly started the Great Chicago Fire of 1871; it’s from an art exhibit called Cows on Parade when 300+ cows paraded up & down Michigan Avenue back in 1999. Look into her eyes. There is a significant iconic Chicago element in each eye.*

world’s largest stained glass Tiffany dome

It’s time to head inside. Once you enter the lobby, look up. You’ll see the names of various authors & philosophers embedded in the stunning mosaics. This is your first clue of the function of this building. This half of the building was the city’s first main library. Next, you’ll see the city crest on the floor in front of the grand staircase that was covered up (by a rug) for many years. Take the stairs up, and you’ll see the first of two beautiful domes. First, the Tiffany Dome in the Bradley Preston Hall (named for the distinguished clergyman, civic leader, and Chicago Public Library board member Dr. Reverend Preston Bradley). And yes, that Tiffany, Louis Comfort Tiffany, the stained glass master. Did you know his father was Charles Lewis Tiffany? He started Tiffany & Co. jewelry in 1837 in NYC. Quite the genes in that family, no?

Here’s a book recommendation about Tiffany: Clara and Mr. Tiffany by Susan Vreeland. 

The Tiffany Dome in the Cultural Center in Chicago
The Tiffany Dome in the Cultural Center in Chicago

As you ascend the stairs into this room, you’ll see the dome & the breathtaking mosaics. This spectacular dome is 38 ft in diameter with over 2,800 faceted glass jewels that sparkle & shimmer as you walk through.  

See if you can find some of my favorite elements. First, look for quotes about the love of learning in different languages, specifically Egyptian hieroglyphs. Second, look for the ‘Y’ surrounded by the letters CPL (Chicago Public Library) and little waves of water. The ‘Y’ represents the confluence of the Chicago River’s north, south & main branches, which is why this beautiful city exists. It was the city’s first municipal symbol/logo; now you’ll see it everywhere. Third, look for the author’s names on the supportive arches; in between, you’ll see ancient printer marks. I’m still amazed every time I come here, and I’m here a lot.

This beautiful space hosts various activities, including free music, dance, theater events, films, lectures, art exhibitions, and family events. And it is a wedding venue. I saw an Indian wedding being set up while giving a tour a few years ago. Luckily, I knew the wedding planner and asked what time the wedding was to come back and get a glimpse. I got back just in time to see the groom arrive on his white horse!

It also hosts an all-night Indian music festival, a Mardi Gras Ball & a Dance-Along Nutcracker, among many other events. Check the Cultural Center website for current exhibits & activities.

Take the ramp/walkway to the G.A.R. Rotunda. This dome, designed by Tiffany and fabricated by Healy & Millet, is a Memorial to the Grand Army of Republic (a branch of the military in the Civil War). Head to the room just on the other side. Look up to see the intricate details on the ceiling.

millennium park

It’s time to head outside to explore Millennium Park. Exit the Cultural Center from the Washington Street side and check out Buddy, a fabulous new shop showcasing local artists’ work.

Stop at the cow & gaze into her eyes. Each eye features an iconic Chicago element. When you do this, leave me a comment with your guesses. Cross Michigan Ave to Millennium Park.

Now head to Pritzker Pavillion. Here, you can enjoy various concerts, movies, dance performances, and much more from Memorial Day through Labor Day, so bring your chairs, blankets, food & drink. Click here for the Millennium Park calendar. Then, look east towards the lake. Here is where you can walk over the bridge to enjoy playscapes and mini-golf at kid-focused Maggie Daley Park.

View of the Pritzker Pavilion from the Lurie Gardens
View of the Pritzker Pavilion from the Lurie Gardens

Looking south of here, you’ll see the Modern Wing of the Art Institute, and in between are the Lurie Gardens. If you are an art lover, the Art Institute is a must, and I highly recommend that you download their app. It is a manageable way to explore this massive museum by genre or by the amount of time you have. Interested in checking out more museums? Here is a money-saving option for you to save up to 40% Go Chicago Explorer Pass. This is a terrific deal if you are traveling with the kiddos.

cloudgate aka the bean

Next, head to Anish Kapoor’s Cloud Gate, aka ‘the Bean.’ As Chicago’s most popular attraction, it’s pretty cool at all times of the day and all times of the year. At first glance, it lures you in to take a closer look. Eighty percent of its surface reflects the sky. It’s made up of 168 stainless steel 1/4 inch panels that have been welded together and is completely seamless. They clean it two or three times each day with a microfiber cloth and water and liquid detergent solution. It also gets a deep pressure wash and wax twice a year.

crown fountain

Next, head north to Jaume Plensa’s Crown Fountain. Here, you’ll see over 1,000 faces of average Chicagoans illuminated on two 50-foot glass block towers—a collaboration of the artist students from The School of the Art Institute Chicago (SAIC).

palmer house hilton hotel

Make your way to the Palmer House Hilton Hotel by walking south on Michigan to the Art Institute. Here the mighty lions greet you. They were originally cast in plaster created for the 1893 World’s Columbian Exposition by Edward Kemeys. Then they were cast in bronze and relocated to their new home.

Take Adams west, then left on Wabash. Enter the hotel here, walk to the escalators, and take them up to the lobby. I love to watch my guest’s faces as we ascend in to this stunning space. The Lockwood Lobby Bar is a lovely spot for a quick refreshment, a drink, or a brownie*, perhaps? Relax as you admire the spectacular ceiling and take in your magnificent surroundings. Want more details? Download the eAtlas app and purchase my Art, Architecture & History, oh my! self-guided tour.

When you are ready to exit, take the escalators going down, then right toward State Street to Adams. On Adams heading west, you’ll see the Berghoff’s sign. This is the oldest restaurant in the city. Owned and operated for four generations by the Berghoff family. They had the honor of receiving the very first liquor license after Prohibition was repealed. Also, women weren’t allowed into the bar until 1969! Last I checked, they were installing a new brewery. They sold the original Berghoff name & brewery and are getting back in the game.

flamingo/federal plaza

Keep heading west to Dearborn. Look left, and you’ll see Alexander Calder’s Flamingo in the middle of the Federal Plaza, which was designed by the father of modern architecture, Ludwig Mies van der Rohe. There are farmer’s markets on Tuesdays from May through October, and chances are you’ll witness a protest or two here on the weekends.

marquette building

Heading north on Dearborn, enter the Marquette Building. Go inside and admire the spectacular Tiffany mosaic in the lobby that depicts Marquette & Joliet’s journey back in 1673.

The Four Seasons mosaic by Marc Chagall
The Four Seasons mosaic by Marc Chagall

four seasons by marc chagall

Exit the building and head north on Dearborn. Just past Monroe, you’ll see the Marc Chagall mosaic, The Four Seasons. This lively & colorful mosaic depicts the various scenes & seasons of the city.

the picasso in daley plaza

Back on Dearborn heading north, you come upon the Picasso in the middle of Daley Plaza. There are farmer’s markets on Thursdays from May through October. This plaza also hosts many other activities, like the Chriskindlmarket, food truck fest on Wednesdays, protests (usually during the weekend), etc.

This is a basic route for exploring the Chicago Loop. If you want to learn and see more, I’d be happy to take you on this tour and share additional details* about the history, art & architecture on this route in person. Please email me at and let me know you want to book my Loop Highlights tour.

This just in! Here are some additional things to do in the Loop: Check out this free downtown adventure through alleys and other off-the-beaten-path locations on this self-guided Loop Mural Walk. Also, coming back this summer is Sundays on State.

If you would like a little more guidance, you can purchase this route. Just download the eAtlas app and scroll through to find Art, Architecture & History, oh my! Or book this tour here to take it in person.

For more information on planning your trip to Chicago, click here for my 3-day Chicago travel guide.

Happy exploring!


  • simplyjolayne

    My husband and I spent only a day exploring in Chicago. Looks as though there is a lot more that we could see on a longer visit.

  • mimi

    Yes for sure! So much to go/see/do. You should come back!

  • Chelsea

    I haven’t been to Chicago but it’s been on my list for a trip this year! I knew about the bean but there’s definitely a lot more to see that I didn’t know about. I’ll definitely be saving this post as I plan my visit.

  • Kelly Francois

    I love visiting Chicago and would love to go back. I enjoyed just walking around admiring the mixutre of old and new architecture. Chicago also has a pretty goof food scene.

  • Jenn

    I had no idea that the Bean is actually called Cloud Gate! Can’t wait to go to Chicago and check out these cool places!

  • Venaugh

    So many great things to do! The stained glass is so beautiful, I’ve never seen one bigger than maybe a door size so that’s absolutely marvellous to see!

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