Chicago in a Day… Things to Do in The Toddling Town

Breaking the curse at Wrigley Field

Things to do with a Day in Chicago

In case you have been living under a rock, the Chicago Cubs are going to the World Series for the first time since 1945.  That is 71 years, folks.  My dad was only eight-years-old when the Cubbies were last there.

As for winning the Series, we have to go back to 1908.  To put that in perspective, both of my grandfathers were born in 1915…seven years after the Cubs won their last World Series.

And while I’m not usually a superstitious person, I just want to point out that the billy goat curse was broken the year my dad and I finally made it out to Wrigley Field.  I’m not saying we broke the curse, but I’m not saying that we didn’t break the curse, either.

If you are planning on paying the estimated $3,500 for a Series ticket in Wrigley, you might want to check out some of the other sites that Chicago has to offer.

Wrigley Field


Might as well start here.  Wrigley Field opened in 1914 as Weegham Park for the Chicago Whales.  The Cubs didn’t start playing there until 1916. It is the second-oldest field in the Majors – after Fenway – and it is a site to behold.  (And I’m not just saying that as a Cubs fan.)

Soldier Field

Soldier Chicago

Opened in 1924 as Municipal Grant Park Stadium and changed a year later to Soldier Field in honor of U.S. soldiers killed in combat.  It was home of the Notre Dame Fighting Irish while their stadium was being built in 1929, as well as various football and soccer teams throughout the years.  In 1971, it became home to Da Bears.

Grant Park


Sitting next to Lake Michigan, Grant Park is known as “Chicago’s front yard”.  Named after President Ulysses S. Grant, the park served as the staging ground for Abraham Lincoln’s funeral procession.  The most famous landmark in the park is the 89-year-old Buckingham Fountain.  You may not know it by name, but when you see it, you can’t help by sing Sinatra’s “Love and Marriage” due to its inclusion in the opening credits of Married…With Children.  (Boy, am I dating myself, or what?)

Art Institute of Chicago


Made famous – at least to uncultured people, like myself – by Ferris Bueller’s Day Off.  Make sure you take your own Cameron-esque photo in front of A Sunday on La Grande Jatte.  Other works of art include Hopper’s Nighthawks and Picasso’s The Old Guitarist.  (American Gothic is there, as well, but not currently on display.)

Union Station

Since we’re on the topic of movies, you might as well stop off at Union Station and take a selfie in front of the stairs where the famous scene from The Untouchables was filmed.  (You probably shouldn’t reenact the entire scene, though.)

Willis Tower

Still commonly called by its previous name, Sears Tower,chicago8edited this 108-story (1,451 ft) building was the tallest building in the world from 1973-2009.  And while other buildings around the world have surpassed it, it is still the tallest building in the United States.

Being from Utah, where our tallest building is a mere 422 ft, just standing at the base of the Willis Tower is panic-inducing.  And then you go to the 103rd floor and stand on the Skydeck.

The Skydeck tour takes about an hour and will cost $22 ($14 for youth), but as they say, “When in Chicago…”

Chicago Tilt

Speaking of getting up high. Check out 360 Chicago observation deck is also home of TILT. This is Chicago’s highest thrill ride where an enclosed moving platform literally tilts you out over Michigan Avenue from the 94th Floor. With its many interactive learning opportunities on the city’s rich history, colorful neighborhoods and its iconic architecture, along with a modern Bar and Café where you can relax and enjoy the best views of the city, 360 CHICAGO is the perfect place to enjoy an unforgettable experience.

Route 66


I am a history nerd.  I am also a music geek, so you know I had to take an opportunity to see the marker of where the Historic Route 66 begins.  (Before we motored west.)

On a somewhat related topic, I made a playlist of some great Chicago songs.  Besides the ones I’ve already mentioned, here is a sampling:

“Take Me Back to Chicago” by Chicago

“The Night Chicago Died” by Paper Lace

“A Dying Cubs Fan’s Last Request” by Steve Goodman

“Chicago Bound” by Jimmy Rogers

“Sweet Home Chicago” by Robert Johnson

“My Kind of Town (Chicago Is)” by Frank Sinatra

Restaurants in Chicago


Italian beef is Chicago’s answer to the Philly steak.  And while there are many places in Chicago to get one, only one has Mike Ditka’s approval: Al’s Beef.  I ordered mine “dipped”, which means they submerge the entire sandwich into au jus.  There are many locations to choose from, so no matter where you are in Chicago, you can find one.


When most people think Chicago food, they think giordanodeep dish pizza.  And Giordano’s does
deep dish right.  A few things to keep in mind when ordering.  First, the pizzas take about 45 minutes to cook.  Next, the pizzas are huge.  My dad and I couldn’t finish a small, which is saying something considering that I am included in that equation.  Finally, Giordano’s opens at 11:00 and gets busy quickly, so get there early.  (Order online or by phone and pick it up.)

One last thing.  Make sure you use the city’s elevated transit system – the “L” – as you travel around the city.  It just enhances the experience.

How to save some Moola in Chicago

Make sure to grab a Chicago with CityPASS before you go. You’ll get VIP admission to the most iconic attractions in the city, hand-picked and packaged into one convenient ticket booklet at a big savings. Because CityPASS is valid for 9 consecutive days starting with the first day of use, there’s no need to rush through each attraction. And skipping ticket lines means you’ll have more time to enjoy the Chicagoan experience—from the city’s famous landmarks and beautiful architecture to the amazing food and warm Midwestern hospitality. The pass includes

Your CityPASS Includes
Shedd Aquarium – VIP ENTRY
Skydeck Chicago – FAST PASS
The Field Museum – VIP ENTRY
Museum of Science and Industry OR 360 CHICAGO – EXPRESS ENTRY
Adler Planetarium – VIP ENTRY OR Art Institute of Chicago – FAST PASS

p.s. Go Cubs!

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One thought on “Chicago in a Day… Things to Do in The Toddling Town”

  1. I was stationed at NTC Great Lakes from 1982 – 1985 as an instructor when I was a young Chief Petty Officer. I tried to get into “the City” as often as possible to see a Cubs or Bears game, to wander Navy Pier or the downtown shopping district, have a cold one down on Rush Street, or rub elbows with some of the town’s movers-and-shakers at the Playboy Club in Lincoln Park West. The people of Chicago were always great and I hated to have to move on to my next duty station in Yokosuka, Japan in ’85. Now residing in Florida, I realize after reading your great article how much I am missing! I have to make a concerted effort to make a visit to “The Windy City” before I get to much further along in my years! Thanks agan!!! Senior Chief Petty Officer, United States Navy (retired)

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