Chicago is a great city for any variety of activities, especially those that keep you outdoors, involve culture, dining, shopping, or any form of entertainment. So, no matter what is happening in the world, there’s always something to see, do or enjoy in Chicago.

Day 1 Parks and the Outdoors

“The Bean” – technically named “Cloud Gate” in Chicago’s Millennium Park is everyone’s park and spot to take pictures. There’s activity, food vendors, street buskers and more happening around the bean in every season. In the winter, this is where you’ll find the Christmas tree.

Nearby is the Maggie Daley Park ice rink in the winter, or roller-skating rink in the summer, it’s a massive quarter-mile loop. The park also has a climbing wall, miniature golf, tennis courts, gardens and more.

It’s also one of the best spots in the city to see the skyline and grab some great photos.

While downtown other parks to visit include:

Chicago Riverwalk

The Riverwalk goes from Lake Michigan through the heart of downtown. Walk along the boardwalk near the water’s edge. There are plenty of places to stop for food, drinks, or even rent a kayak and see the city from the water. The Chicago Architecture Center offers architectural boat tours that are a must-do.

Navy Pier

Navy Pier along the edge of Lake Michigan is filled with shops, dining, live music, a botanical garden and various events and things to see and do, including the giant Ferris wheel. It’s an excellent place to spend an afternoon. It’s where you can catch a sailboat or take a tour of Lake Michigan.

Lincoln Park

Not just a music band, it was a famous park first. Lincoln Park has over 1,100 acres, including walking trails and ponds, the Lincoln Park Zoo, the Chicago History Museum, lily ponds, nature sanctuaries, archery ranges, sports fields and much more. You’re also going to find statues of Lincoln, Grant and others with Chicago history.

Day 2 Museums

“Art is what you can get away with.”

– Andy Warhol

Chicago has dozens of amazing museums, but you can only see so many in a day. Here are three good ones unique to the city.

Art Institute of Chicago

The Art Institute of Chicago is among the best in the country. They have a spectacular modern and contemporary art collection, but specifically, their Impressionist collection is excellent.

Art on display includes: “A Sunday on La Grande Jatte,” by Pointillist Georges Seurat, “American Gothic,” by Grant Wood, a series of “Stacks of Wheat (End of Summer),” by Monet, and “The Bedroom,” by Vincent van Gogh. These plus work by Andy Warhol, Jackson Pollack, Diego Rivera and many others can all be found within its walls.

The American Writer’s Museum

The American Writer’s Museum is down the street from the Art Institute on Michigan Ave.

There are quotes on the walls and books hanging from the ceiling. There’s a children’s writers’ section in which young and old alike will find much merriment. It brings the stories into the real world in a playful way for exploration. Down the main hallway is an interactive timeline of writers with their best-known quotes, audio and information about their lives and works.

“All good things are wild and free.”

Henry David Thoreau

The Field Museum

If you’re in Chicago, you must see Sue. She’s Chicago’s most famous resident and the world’s largest, most complete Tyrannosaurus Rex fossil. The Field Museum also has a 70-ton Argentine Titanosaurus and enough bugs, plants, gems and animal taxidermy to blow your mind.

Other museums to consider:

• The Museum of Science and Industry
• Frank Lloyd Wright Home and Studio
• The Hemingway Museum
• Chicago History Museum
• The Museum of Contemporary Art

Day 3: Shopping in Chicago

Chicago has a strip called The Magnificent Mile solely because it has many places to purchase things. People LOVE this. They come by the thousands to go into and out of these shops laden with bags.

Here you will find:

• Tiffany’s
• Neiman Marcus
• Nike
• Starbucks Reserve (it’s huge and spectacular)
• Zara
• Nordstrom
• Lush
• North Face and many, many others

But, the Mag Mile is just the main strip; there is plenty of small business shopping in some neighborhoods.

Lincoln Park isn’t just a park; it’s also a neighborhood. Near the streets around Armitage and Halsted, you’ll find shops and boutiques in historic row homes and little enclaves down the side streets.

Wicker Park is less boogie and more artsy than downtown. Shoppers can find vintage and the unique or unusual, plus several affordable galleries. Like all neighborhoods in Chicago, there are a lot of places to eat and drink, but this one is known for its upbeat nightlife.

Logan Square is a quieter neighborhood with smaller shops surrounding larger homes and upscale townhomes. Here, you’ll also find the historic Logan Theatre, small-batch breweries and distilleries, and Michelin-rated restaurants.

Honestly, three days isn’t nearly enough to see or do half of what you’ll want to in Chicago, but it’s a good reason to make frequent visits, or a much longer stay.

See other posts about Chicago here.

Let’s Connect on Social Media and Email

• Instagram
• Facebook
• TikTok