See the Artsy Side of Chicago


Ask me what I love most about Chicago, having lived there for nine years, and my hands cannot type fast enough.  Ask me for 10 of my favorite things to do in Chicago and I beg, “Can’t I do twelve?”

Culturally and experience wise, Chicago is truly one of the richest cities in the world. Plus they make their hotdogs differently than any other place around. For example: Ask one of the real old-timers to add ketchup to a dog and they will flat out refuse.

I could tell you where to walk your dog and how the Printer’s Row area, near where my home was, offers the best sidewalk cafes. Okay, Okay… I’ll get on with it.   Take a car, take a plane, but get there any way you can!

Here is my list of how to see this town like a native.

Chicago Skyline
Photo credit: tpdave via Pixabay

1. Lookingglass Theatre

This theatre was founded by David Schwimmer (from Friends) and others in 1988. It is considered one of the best regional theaters in America.  It is located inside the Water Tower Water Works Building on Chicago’s Magnificent Mile. Great surroundings, cool area of the city and good theatre.

things to do in Chicago: visit the Lookingglass Theatre
Photo credit: myBestAddressBook

2. The Chicago Cultural Center

The Chicago Cultural Center is the home to the world’s largest stained-glass Tiffany dome. Head to the 4th floor to get a great look at the dome and the scholarly quotes that encircle its base. Wander the halls and awe at the exhibits. The Chicago Department of Tourism has an office at the front at 78 E. Washington Street.  You will find lots of free culture in one beautiful building; plus get all the tourist information that you could ever want.

Things to do in Chicago: visit the Chicago cultural center
Photo credit: Kymberly Janich via Flickr CC

3. Frank Lloyd Wright’s Chicago

Frank Lloyd Wright had a studio and office on the plate.16th floor of the Monroe Building (104 S. Michigan Avenue) which is not as well-known as his studio, home and various sites in Oak Park and in Chicago.

The Monroe Building is an easy walk from the Art Institute and Palmer House.

The building has been renovated recently and other tenants occupy that floor.  When I lived in Chicago, I often ducked into this lobby to get out of the wind or rain.  The Monroe Building is a master piece of Rookwood Tile and Pottery.

Things to do in Chicago: Visit the Monroe Building
Photo credit: Steve Chou via Flickr CC

4. The Peggy Notebaert Nature Museum

Want a moment of peace and wonder? This is a must. All ages love this hidden gem. The feature that draws me back is the butterfly garden, which is housed in their 2700 square foot greenhouse.

Things to do in Chicago: Visit the Peggy Notebaert Nature Museum
Photo credit: Kenneth Spencer via Flickr CC

5. The Walnut Room at Marshall Field’s on State Street (Macy’s)

Talk about old world charm, talk about romance and tradition, and you will find yourself at the Walnut Room in the former Marshall Field’s store, now Macy’s on State Street.  The Walnut Room opened in 1907 and is the first restaurant ever opened in a department store.  It is America’s longest running restaurant.

Things to do in Chicago: Macy's Walnut Room
Photo credit: Michael Kappel via Flickr CC

6. The Art Institute of Chicago

The Art Institute of Chicago has one of best Impressionist collections in the world.  Be inspired – take a day or afternoon, or whatever time you can spare.  You can see everything from Grant Wood to Monet to Hopper, and hundreds of thousands more works of art.

Things to do in Chicago: Visit the Art Institute of Chicago
Photo credit: one2c900d via Flickr CC

7. Palmer House Hilton Lobby

This exquisite work of art inside a building is one of the best people-watching spots in America. Order coffee and one of their famous brownies or drinks – your choice. Brownies were invented at the Palmer House when Bertha Palmer requested that the chefs make a cake that could be held in one’s hand.  They were first served at the 1893 World Columbian Exposition.

Things to do in Chicago: Visit the Palmer House Hilton Lobby
Photo credit: Brett Kiger via Flickr CC

8. Walk Grant Park, Millennium Park, the lake front (Lake Michigan)

Does that count as three things?  Well, don’t miss them.

Things to do in Chicago: Visit the  Bean in Millennium Park

9. Willis Tower

Willis Tower, formerly Sears Tower, is currently the tallest building in North America.  You must go to the SkyDeck.  It is 103 floors up.  If you can splurge, go to the Metropolitan Club for a meal.  Awesome view, all very romantic!

Things to do in Chicago: Visit the SkyDeck on Willis Tower
Photo credit: ed_needs_a_bicycle via Flickr CC

10. Garrett’s Popcorn

What would a trip to Chicago be without Garrett’s Popcorn?  It is worth the wait on line.  If you want to snack like a Chicagoan, order the cheese and caramel combo. If you are going to the Cultural Center or the Palmer House, there are several locations nearby.  Try the ones on 4 East Madison Street or 26 West Randolph.

Things to do in Chicago: Snack at Garrett's Popcorn
Photo credit: courtney via Flickr CC

11. Baseball

Chicago is a town divided when it comes to sports.  I learned when I moved there that you cannot be a Cubs and a White Sox fan.  You have to decide.  So pick your team. Check out your favorite, if you are there during the season.  I love Wrigley Field and the area around it, but I am a history buff.  Ask my best friend and she will tell you all the reasons to love the White Sox.

Things to do in Chicago - Attend a baseball game
Photo credit: Andy Sternberg via Flickr CC

12. Chicago Architecture Foundation River Cruises.

You have to see Chicago from a boat to really get the grandeur of it all.  The Chicago Architecture Foundation has a great gift shop and display at their headquarters on South Michigan Avenue.  I think they offer the best cruises.

Things to do in Chicago: Go on an architectural river cruise
Photo credit: _e.t via Flickr CC

That’s twelve with a few snuck in here and there.  Did you count them?  I can’t say enough about Chicago.  If you have never been, you must put it on your travel bucket list.  If you are a “regular”, you know there are diverse neighborhoods to see, pizza to sample, an architect’s dream of buildings to explore, a lake that resembles an ocean, and so much more.

And one bonus item! One more of my favorite places to study, research and dream: the Harold Washington Library on State Street!  I love the 9th floor which houses rare collections and materials focusing on Chicago. This top floor has an atrium with walls of glass, a wonderful place to sit with a friend or with your thoughts. Now, that is Chicago. Go have fun!

Author Bio

Joan Greene is a multi-award winning giftware and toy designer and writer who currently lives in Nashville, Tennessee.  In addition to her design work, Joan is the author of five books, numerous articles, and is a voting member of the National Academy of Arts and Sciences (The Grammy Awards)