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Top Sites of Downtown Chicago

“What are we going to do in Chicago?” Jason asked as we were driving to LAX to catch our flight. He knows I love to plan our trips and that I research all of our options thoroughly, maybe even obsessively. But when it came to planning things to do in Chicago, I must admit I was struggling. This is the town where I was born and spent my first fifteen years. So I had a long list of childhood haunts that I wanted to visit combined with many attractions I had never seen. How was I going to sort this out in only four full days? Essentially, we split the difference, finding time for me to stroll down memory lane while also trying out many new places. (Looking for even more to do in Chicago, then read this post.)

Tour guide, Hilary, leading Free Tours by Foot

Exploring the Loop with Free Tours by Foot

Chicago is the third city in which we’ve taken a free walking tour, and we’ve never been disappointed.  What’s especially important to point out though, is that each of our free tours was managed by a different company.  I’ve come to the conclusion that this method of offering tours is mutually beneficial for the tour guides and tourists alike.  Yes the tour is free, but you are encouraged to tip the guide in cash at the end according to your experience.  Our guides have always been informative and entertaining.   For Chicago we selected the Loop tour organized by Free Tours by Foot.  Our guide, Hillary, told us of how she came to Chicago three years ago with the program Teach America.  She didn’t fall in love with teaching, but did find herself a new home in this Windy City, and now works full-time providing walking tours all over the city.  We began at the historic Chicago Theater, wound our way through a number of stops and ended at the very modern Millennium Park.  Hillary shared historical facts, funny stories and even a few local legends. The whole tour lasted about two hours.

Wandering Through Millennium and Maggie Daley Park

Cloudgate at Millennium Park

When I was kid, this part of the city was rail yards.  Let me point out that rail yards are pretty ugly places full of fume belching engines, old wood and metal tracks, and plenty of trash.  Former Mayor Richard M. Daley’s vision to replace those yards with Millennium Park was a gift to the city of Chicago. A few years later the family friendly Maggie Daley Park was added.  In combination, this space now offers something for everyone--fountains, an entertainment venue, outdoor art exhibits, secluded gardens, large lawns for picnics, and unique playgrounds for children.  And I would be remiss if I didn’t mention that Millennium Park is home to one of the most instagrammed sites in the U.S., Cloudgate, or in local vernacular, “the bean.”

Here's a great article about romantic getaways in Illinois.

Enjoying public art display, sculpture by Chakaia Booker

Visiting Grant Park and Buckingham Fountain

Early one morning I insisted that Jason and I walk to Grant Park in search of Buckingham Fountain, one of the largest fountains in the world.  Visiting this fountain was one of my fondest memories as a kid.  We often went at night during the summer to see the fountains light show, and I never got tired of it.  This used to be a major tourist draw for Chicago, but has since been supplanted by Millennium Park.  However, these parks are both worth a visit and less than half a mile apart.  On the day Jason and I visited Grant Park we had it to ourselves.  In addition to the fountain there is a lovely rose garden and a number of public art displays.

Buckingham Fountain

Exploring the Art Institute

Located between Millennium  and Grant Parks is one of Chicago’s top attractions, the Art Institute. It also happens to be one of the world’s top museums.  This isn’t just my designation, this museum is often included in lists of the world’s best museums, and for good reason.  The combination of two beautiful parks flanking such an impressive museum makes this stretch of Michigan Ave. one of my favorite places in the U.S.  I could return here for years and never become bored.   

Lion in front of the Art Institute

While the Art Institute now offers multiple entrances, I recommend starting on Michigan Avenue so you do not miss the lions.  Yes, the lions aren’t real, they are sculpted from bronze, but in Chicago, these lions come alive and are a part of the culture.  I can’t prove this, but it’s possible that these lions are in more photographs than ‘the bean.’  At Christmas they wear large green wreaths and when a local team wins a championship, they wear special attire.  For the miraculous Cubs championship of 2016, special blue baseball caps were made.  

But I digress. This museum is impressive.  If you enjoy any type of art, then you need to set aside at least half a day to explore.  The Art Institute houses the largest collection of French Impressionism outside of France.  Paintings that you’ve seen in books, magazines and online are housed here--Van Gogh’s self portrait, Seurat’s A Sunday Afternoon, Wood’s American Gothic, and many more.  A modern wing was added in 2009 and ever since the museum has been adding to this collection through acquisitions of Warhols, Koons, Lichtensteins, and many others.  

Interior of Art Institute, original building
Interior of Art Institute, modern wing

If you are traveling with kids or grandkids, do not think that this is some stodgy art museum that will bore children.  I was delighted to see kids and their parents enjoying self-guided family programs through the Art Institute’s Ryan Education Center.  My sister and I participated in similar activities when we were young and I’m confident these were the experiences that began my own interest in art.

The cost of admission is currently $25 for adults from out-of-state.  We also opted to rent the audio tour for $7 more and found it very informative.  My recommendation is to arrive at the museum when it opens at 10 a.m. to enjoy minimal crowds.

View of Chicago's skyline from the river

Cruising the River on an Architectural Boat Tour

While growing up in Chicago I had often seen these boats packed with people floating up and down the river.  It seemed like the same sort of touristy activity that any city in the world with a body of water offers.  So imagine my surprise when I started researching Architectural Boat Tour and saw that it was one of the top rated activities in Chicago according to TripAdvisor.  Seriously?  What was I missing?  It turns out I had been missing a great deal.  These boat tours provide a wealth of information about the history and architectural significance of the city of Chicago.  And it turns out that since the river cuts through the heart of the city, it’s a fabulous way to view many of the architectural highlights.  Add to all of that a tour guide with her Masters degree in architecture and I was feeling like the $33 per person ticket was worth every penny.  We opted for an evening boat tour which I would highly recommend.  We boarded at 5:30 p.m. and enjoyed the sites in daylight on our way out, and then enjoyed many of the same places at sunset or after dark on our way back.

Historic bridge seen during boat tour

Strolling the Riverwalk

The river can definitely be enjoyed from a boat, but thanks to a redevelopment project started in 2001, it can also be seen on foot.  The almost two miles of paths meander along the river and offer many opportunities for relaxing, art viewing, dining or partying.  Jason and I opted for a morning walk when this area is least crowded.  Its definitely noisy at points as you walk under major streets and bridges and hear jack hammers pounding--part of large construction  projects nearby.  But something about being just below the city streets provides a nice respite from the busier city life above.

Chairs along Chicago's Riverwalk
View of the city from Chicago Athletic Association

Getting beyond downtown Chicago and exploring the entire city could take weeks, even months.  There’s much to see in the 77 neighborhoods that comprise Second City.  But if you only have a few days, don’t despair, because the beauty of Chicago’s Downtown--or Loop--is that its relatively small and compact and therefore possible to visit the top sites in two or three days.  You’ll leave with an understanding of what makes this place special as well as plenty of Instagram-worthy photos.  

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This Post Has 2 Comments

  1. Catherine

    I live in Chicago, and this is a GREAT overview of things to do! How fun that you were born here and that you were able to visit some of your old haunts. Great tips on visiting Maggie Daley and Millennium, Chicago has so many free things to do. Thanks for highlighting that! I also love the river-walk and the architectural tour. What was your favorite museum?

    1. Wendy

      Thanks for all of your kind words, Catherine! As an adult my favorite museum is the Art Institute, but as a kid I absolutely loved the Museum of Science and Industry. We went there all the time and I never got tired of it. You are fortunate to live in such a cool city.

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