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  • Writer's pictureChristina Trotter

36 Epic Things to Do in Chicago

Updated: Aug 5, 2023

Chicago has always been one of my favorite cities. My sister has lived there for over 30 years and our family makes at least two trips a year to the city. Once, before Bill and I were married, I declared that I was going to move there. He declared that he was not.

I still live in Dallas.

I love Chicago because it is a big town with a big heart. Generally, Chicagoans have that friendly mid-western attitude and the city's pace is slightly slower than NYC. You don't feel like you are infringing on someone's time if you need to ask a question or get directions.

Then there's the food. Oh man, my mouth is watering just thinking about an Italian Beef sandwich dripping with au jus and topped with giardiniera peppers. [Side bar: While everyone was making sourdough break in 2020, my first pandemic recipe was to make Italian beef in the slow cooker and then make hoagie rolls from scratch. It. Was. Awesome.]

While in Chi-town a few weeks ago, I sat down with my sister and brother-in-law and made a list of the things that we think every first-timer must-see. If you are Chicago trip planning, here are our recommendations:

Table of Contents:

See the City from a Skyscraper

Willis (Sears) Tower

It stands at 1,730 feet tall, including its twin antennas, and is the 12th largest skyscraper globally. The Willis Tower Sky Deck has a large glass platform where you feel like you are floating over the city. It's not for those with a fear of heights as Bill will tell you. Here are some fun facts about Willis Tower.

  • 233 S Wacker Dr

The Willis Tower as seen from the ground looking up
Willis Tower

John Hancock Tower

For nearly as high with fewer people and a view that many prefer, try the John Hancock Tower. It stands 1,127 feet tall. My sister says to check out the view from the women's room at the's amazing. Only do that if you are supposed to be in there;)

  • 875 N Michigan Ave

Shop the Magnificent Mile

Below I list the most popular things to do along Michigan Ave., more commonly referred to as the "Mag Mile". I like to window shop and go into any stores that strike my fancy.

Get popcorn at Garrett's

Folks line up outside of Garrett's to get their "Chicago-style" popcorn, a mix of cheddar and caramel popcorn to create a sweet and savory treat.

  • 625 N. Michigan Ave.

See the Historic Water Tower

Water Tower stands out along the Mag Mile with its glistening limestone built in the Gothic Revival style. It was built in 1867 to house the water for the growing population. Water was pumped from 2 miles out in Lake Michigan and stored there. But its real claim to fame was to be one of the only buildings to survive the Chicago Fire of 1871 (if you're a Girl Scout, you know that's the one that Mrs. O'Leary's cow started:)

  • 806 Michigan Ave.

Go shopping at American Girl

If you have a little girl that's into dolls, this will be a wonderland for her. I am thankful that my kids were never that into dolls because you could take a vacation on what some of this stuff costs. If your child doesn't know about it, may I recommend skipping this? But I hear it is magical, so if you have the money and the inclination...:)

  • 835 Water Tower

Ride the Ferris Wheel at Navy Pier

Navy Pier started as Municipal Pier in 1916 and was renamed after it housed sailors during World War I. In 1995, it was renovated to include a Ferris wheel, theatre, shopping, and dining. Some of our favorite things to do at Navy pier are:

Walk the Lake Front and Sun yourself on Oak Street Beach

When it's nice weather in Chicago, everyone goes down to Lake Shore Drive. You can see people walking, biking, and rollerblading. But the most happening place may be Oak Street Beach. Here you can lay a towel in the sand and read a book or catch a volleyball game.

  • 1000 N. Lake Shore Dr

Walk Through Grant Park, Chicago's "Front Yard"

Grant Park includes Buckingham fountain, lovely landscaped gardens, Millennium Park and the Museum Campus.

  • Buckingham Fountain, 301 S Columbus Dr

  • Millennium Park, 201 E. Randolph St.

Cloud Gate is a large, stainless steel sculpture that stands 33 feet high and looks like a bean. You often see people posed in front of in pictures of the city. You can see the reflection of large buildings in the background. It's fun to stand underneath the bean and to see it from different angles.

Two girls stand in front of Chicago's Cloud Gate sculpture with the city's skyline in the background.
My niece and daughter in front of "The Bean"

This massive park is unlike any park that I've ever visited. It has the typical castle-like structures, but it also has really fun warped slides built into the hillside. And there are lots of other activities like a climbing wall, mini-golf, and a cancer survivor's garden. Our kids loved spending time at this park and so did their pre-teen cousins, even if they didn't want to admit it.

In winter, the Maggie Daley Ice Skating Ribbon and Millennium Park Ice Rink are not to be missed. The Ribbon goes around a good portion of the park and is filled with skilled and novice skaters.

Tour the Museums

The museums are all fabulous and many are near one another, especially Shedd, Adler, and Field which are all co-located. If you had to pick only one or two, go with whichever topic interests you the most because they are truly all outstanding. My favorite is the Adler Planetarium followed by the Field Museum but that's just because I love planetariums and history. Go with your gut on these.

Walk through the Lincoln Park Zoo and Stop for a Beer Nearby

Lincoln Park is a beautiful neighborhood just north of downtown Chicago. There are lush, landscaped gardens and beautiful parks and activities. The zoo was built in 1868 and it is open-air and free and a must-do if you like zoos. After so much walking though, you probably will be ready for a beer.

Catch a Game at Wrigley Field

We've gone to Cubs and Sox games, but there's nothing quite like being at Wrigley Field. It's iconic and a lot of fun.

See a Show at The Second City

Wanna see where Chris Farley, Jason Sudeikis, Amy Poehler and so many more got started? It's always fun to watch an improv show at Second City.

Take a Tour

Architectural Tour

Even the locals love this tour! Many companies offer an architectural tour, but the Chicago Architectural Foundation is the best. Learn about key buildings in the skyline as you navigate the Chicago River.

Our family stands on a bridge in Chicago overlooking the Chicago River. There are several skyscrapers in the background.
On a bridge overlooking the Chicago River

Devil in the White City Tour

If you haven't read The Devil in the White City by Erik Larson, you should put down whatever you are doing and buy it now. It is one of my Top 10 favorite books of all time. The book - and the tour - are based on true historical events surrounding a mass murderer whose killing spree aligns with and becomes intertwined with the 1893 World's Fair, held in Chicago. Note that this tour is offered infrequently, so plan if you want to do it.

The Devil in the White City is one of my Top 10 favorite books. It's a fast-paced thriller based on real historical events that will also give you a better appreciation for the architects and landscape designers that so heavily influenced Chicago's design.

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How to Get There

There are two large airports in Chicago. Most airlines fly into Chicago O'Hare. Southwest flies into Midway.

Where to Eat

The dining scene is always changing, but I prefer to stick to the classics, especially for a first visit. Here are some of my recommendations:

Portillo's for Italian Beef

Portillo's is a chain throughout the Chicagoland area, but they serve a great Italian Beef. Don't worry if your group has picky eaters, they also have pasta, burgers, chicken sandwiches, salads, and more. It's Chicago street food!

Gino's East or Giordano's for Chicago-Style Pizza

If you aren't familiar with Chicago pizza, you need to try it at least once. It's an experience. It's deep dish and above the crust, it's layered with cheese first, followed by toppings and sauce. I'll stick to Portillo's, but I know there are lots of fans.

You're in the Midwest - eat Steak!

There are tons of great steakhouses in Chicago, but these are some of our favorites. I haven't tried El Che yet, but it is Argentine-style - yum! - and the Robb Report named it one of the Top 25 steakhouses in the country.

The Wiener's Circle for a hotdog

A Chicago institution since 1983. Yummy street food served with an attitude. Maybe skip if you have the littles with you or have someone wait outside while you order.

Eat Dinner in Greek Town and/or Little Italy

You can always count on a good meal in the ethnic neighborhoods. Here are our picks:

Where to Stay

My favorite place to stay is Palmer House. The rooms are small but beautifully decorated. It's in a great location on Michigan Avenue so that you are central to many of the places that you'll likely want to visit.

If you are limited on time, stay and play along Michigan Avenue. There are so many things on this list that are in close proximity.

As always, please save this or forward it to someone who may find it helpful. Every like, share and save helps me to help you!

Happy Travels,



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