Annie Zhu’s Day Off: How to Spend 24 Hours in Chicago

This travel guide is Ferris Bueller inspired, as my main research for the trip was rewatching this John Hughes classic. I didn’t hijack a parade or watch a Cubs game, but I did see priceless pieces of art and felt peace (and fear) at 1,353 feet in the air.

I was in Chicago in the middle of June to volunteer for 5 days as a Zohar Project¬†mentor. Throughout the experience, I met some really amazing locals within the city and the surrounding towns, as well as connected with local Kabbalah student volunteers. My schedule was jam-packed on those days, so I’d booked myself in for an extra day to explore the city as a tourist. This is the itinerary I’d recommend if it’s your first time in Chicago and you only have 24 hours. Especially when it’s a perfect sunny day in June.

8:00 a.m.

(L) Sunny Side Up; (R) Yolk

Fuel up with an epic breakfast at Yolk or Sunny Side Up.

9:00 a.m.

Visit Cloud Gate (“The Bean”), Crown Fountain, and Jay Pritzker Pavilion at Millennium Park.

Cloud Gate “The Bean”

Bottom of Cloud Gate

Inspired by liquid mercury, Cloud Gate is a sculpture by British artist Anish Kapoor.¬†Be a tourist and take a bunch of pics here because, as my friend Alex said, “Isn’t it amazing how a piece of art can make so many people happy?”

Crown Fountain is right beside Cloud Gate. It’s another interactive art installation making people happy. Kids love it, as you can see from my photos. Two glass block towers project faces of Chicago’s diverse citizens. Sometimes they open their mouths to “spit” out water.

The Jay Pritzker Pavilion holds free concerts and events. Frank Gehry designed, this is one of the world’s most state-of-the-art outdoor music pavilions.

11:00 a.m.

Visit The Art Institute of Chicago.

A Ferris Bueller hangout, where I saw numerous priceless pieces of art. This museum is one of the best in the world. I could’ve easily spent the whole afternoon here. Below are some of the iconic pieces I was most enthusiastic to find.

A Sunday Afternoon on the Island of La Grande Jatte by George Seurat

The Bedroom by Van Gogh

Nighthawks by Edward Hopper

12:45 p.m.

Try Chicago’s famous deep dish pizza for lunch.

A local recommended Lou Malnati’s, which is known for their buttery crusts. I got my pizza customized with spinach, cheese, and mushrooms. It’s like a quiche. There’s also Uno and Due, which are quite famous as well. Another friend recommended Giordano’s, so you’ve got options.

2:00 p.m.

Step onto the glass ledge of Skydeck.

Another Ferris Bueller hangout. As Ferris famously said, “Anything is peaceful from 1,353 feet.”

Not sure about that. This was kind of scary. The glass ledges were put in 8 years ago. I’m not super scared of heights, but I couldn’t look down when I stepped onto it. Some friends got freaked out just looking at my photo on Instagram.

Skip the long lineups and buy the entrance ticket in advance. When I went to The Art Institute of Chicago, I bought a ticket that allowed me entry into both attractions.

4:30 p.m.

Walk the Magnificent Mile.

The Magnificent Mile is a good stretch of Michigan Avenue, ending at the Michigan Avenue Bridge. This is Chicago’s Champs-√Člys√©es or Fifth Avenue. You’ll find upscale shops and department stores, as well as beautiful architecture to admire.

I thought the neo-Gothic Tribune Tower was neat. Its exterior walls are embedded with bricks and rocks from historically important sites around the world.

Michigan Avenue (DuSable) Bridge

If you have time, the Lakefront Trail is a lovely walk too.

6:30 p.m.

Eat dinner.

Freshen up at the hotel and grab dinner nearby. I really like Beatrix.

8:00 p.m.

Take Chicago’s Architecture Tour at Sunset.

Wendella’s narrated boat tours are about 75 minutes. This is a must-do for tourists. Your tour guide will tell you about the history and architecture of Chicago’s landmark buildings, and you’ll see the city’s beautiful skyline at sunset (sunset time varies during time of year).


I stayed in the Hyatt Centric Chicago Magnificent Mile Hotel because my event called for it. The location is convenient for the first-time visitor because it’s right in the centre of town and close to major attractions. The Hyatt was awesome, but if I go back, I’d stay in an eco-friendly hotel like the Hotel Felix,¬†Chicago’s¬†first hotel awarded the Silver LEED certification. ¬†Book through Wander, as they give back to worthy charities when you book hotels through them.


I wouldn’t recommend renting a car to get around Chicago. Traffic can get brutal. Take public transportation whenever possible. If you don’t have a lot of luggage, do yourself a favour and take the subway from the airport. Locals are always complaining about rush hour traffic, and some of my friends did get stuck for hours in cabs coming from the airport.

Also check out Litterless’s zero waste Chicago guide¬†for more ideas.

Let me know your must-dos in Chicago in the comments below.

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