19 Best Things To Do on Your First Trip to Chicago and Wrigley Field

Two of America's most fabulous destinations, the city of Chicago and the friendly confines of the coolest stadium in baseball, Wrigley Field.

Things To Do on Your First Trip to Chicago

Do you remember the first time to visited the third-largest city in the United States?

Chicago is the kind of city you can't forget. Even though I grew up only a couple of hours from Chicago, I never made it to the Windy City during my childhood, I was 30-years-old when I made my first trip to Chicago to see a Bulls game in 1995 at the United Center.

To finally see all of those buildings up close for the first time was breathtaking, I was also the driver, so my passenger was a nervous wreck as I could barely keep my eyes on the road. That's another thing about Chicago, driving on the freeway is a big task if you've never driven near the downtown area of a major city.

Things To Do on Your First Trip to Wrigley Field

A few months after my first Bulls game, I had my first Wrigley Field experience. It was a Big Brothers bus trip with our 'littles' (as we referred to the young boys we mentored). A sun-filled June afternoon with baseball, great hot dogs, and a seventh-inning stretch with Harry Caray.

When someone asks you what things to do and check out when they visit Chicago, what do you suggest?

If it's their first time visiting both Chicago AND Wrigley Field, what should be on the 'Must-Do' list?

Someone asked for suggestions for their first trip to both places in a post to a public Facebook group I belong to, Chicago Cubs HQ, and he got over 700 suggestions. Even if you've been to Chicago and Wrigley several times, you'll find things to do you never even thought of or knew about.

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These were my favorite suggestions.

Often, there will be a band playing at the Cubby Bear on game day.

If you want sausage on your Lou Malnati's deep-dish pizza, be sure to order 'pieces' of sausage, otherwise, it will be a sausage patty the same size as your pizza covering the entire thing.

My wife is the biggest Cubs fan I know, and we take that moment every time we walk into Wrigley.

I have no comment.

No ketchup ever.

The Navy Pier Ferris wheel is a great idea.

If you don't have a photo by The Bean, you were never really in Chicago.

100%!

If you love Chicago and Wrigley Field, what else would you tell a first-timer?