21 Best Things to Do in Chicago

The Windy City is famous for a lot of things: Classic architecture and Skyscrapers; World Class Museums and iconic neighborhoods; a vibrant waterfront packed with parks; and of course, the pizza and hot dogs. In this article we’re gonna talk about the best things to do in downtown and greater Chicago.

There are a lot of big cities in the United States, and few of them are as clean and friendly as Chicago. Don’t laugh! We are serious. Chicago is going to surprise a lot of people.

Is Chicago Safe to Visit?

Yes and No. We cover this at the end of the article in our Honest Review.

Is Chicago Worth Visiting?

Chicago is not only worth visiting, it should be on everyone’s short list of US Cities they have to see before they travel overseas. Chicago is required viewing, that’s what we’re saying.

The lakefront museums are in a league of their own, the Downtown skyline is awe striking, and windy Lake Michigan is the perfect backdrop for an active town full of active people.

Chicago wants you here. They built the parks and the overindulgence of entertainment for locals and travelers alike. You don’t have to go to Europe to see a magnificent city. We’ve got one right here in the good old USA (and it’s not necessarily New York).

We spent three months chasing good times around the Windy City. We went to the ballgames. The historical sites. The lakeside beaches. The splendid gardens and hallowed viewpoints. The cheese on your chin forsaken deep-dish pizzas you’ll most certainly regret.

We tried to do it all and came damn close.

These are what we found to be the best things to do in Chicago; the things that we would recommend to our friends and strangers alike. We hope you enjoy reading about them.

Must Do: Things to Do in Chicago

Must-Do attractions are typically the reason we’ve decided to visit.

Field Museum of Natural History

The Field Museum is home to Sue, the largest T-Rex known to man, as well as the Tsavo Lions (of Ghost and the Darkness fame) and one of the most comprehensive collection of animals on earth. The dinosaur exhibits are fantastic, as is the meteorite exhibit, the gems and jewels, etc.

Lakefront Trail and Riverwalk

Some of the most beautiful scenery in downtown Chicago is along Lake Michigan and the Chicago River. Stroll from the Shedd Aquarium to Navy Pier, then follow the Chicago River into a fabulous section of town. The mirrored buildings and bright blue waters are so beautiful it would be tragic to not walk as much as you can tolerate.

Lincoln Park Zoo

The Lincoln Park Zoo is one of the best free zoos in the United States and it is open 365 days a year. There are over 200 species of mammals, reptiles, and birds on display in these beautiful grounds. Lincoln Park is definitely one of the best things to do in Downtown Chicago.

Chicago Cubs Game

Any respectable baseball fan will visit Wrigley if given the opportunity. It is one of the most famous venues across all sports.

Parking is about $50 near the stadium. If you’re willing to walk a half-mile or more, metered parking can save you most of that, but you’ll have to hunt for it. We found a place north of the stadium HERE and it cost about $12 for the three-hour game.

Galloping Ghost Arcade

The Galloping Ghost claims to be the largest arcade on earth, boasting over 800 stand-up arcade-style games. If you have a favorite childhood game that you can never find, it’s almost a guarantee these guys have it in one of their four packed rooms.

Admission is $25 for all-you-can-play action. Hours are from 11:00-midnight on weekdays, and 11:00-02:00 on Fri/Sat.

Adler Planetarium

If you’re an interplanetary space geek this is your Xanadu. The Adler Planetarium is home to an abundance of things pertaining to the universe, and includes the Doan Observatory (a large telescope), and an assortment of Sky Shows in their immersive dome theaters. Easily one of the best things to do in Downtown Chicago and one of the best space museums in the USA.

Waterfront Parks

The waterfront in Downtown Chicago has an collection of contiguous parks that rival any US city. All of them backdropped by the magnificent Chicago skyline, the parks flow seamlessly, one into another, composing a ceaselessly strollable milieu.

The heavily photographed Millennium park (above) is home to the famous “Bean” sculpture, and Maggie Daley Park is a children’s wonderland. Other noteworthy parks include Grant Park, Lakefront Park, Buckingham Fountain, and Lurie Garden.

Art Institute of Chicago

The Art Institute of Chicago is considered by many to be the best art museum in the United States (outside of New York City). Some of the highlights include: American Gothic, Nighthawks, Waterlilies, one of Van Gogh’s self-portraits, and A Sunday Afternoon on the Island of La Grande Jatte (which is simply phenomenal).

The Chicago Art Museum is easily one of the best things to do in Downtown Chicago.

Should Do: Things to Do in Chicago

Should-Do attractions receive a strong recommend.

Chicago Botanic Garden

Widely considered one of the top botanical gardens in the USA, this 385-acre arboretum features 28 different gardens and draws more than one million visitors annually.

Deep Dish Pizza

Deep dish pizza to Chicago is like bad haircuts are to Seattle. If you move to Seattle, you’re gonna look like an overused crayon eventually. And if you come to Chicago you’ll most certainly eat the pizza.

Lou Malnati’s is the best. Giordano’s, Gino’s East, and Rosati’s are pretty good. Pequod’s was supremely disappointing.

Six Flags Great America

Six Flags Great America is consider by most to be one of the top 10 roller coaster parks in the United States. Our family can’t exactly validate the claim, as this was one of the things we missed during our three months living in town Feb-April. Some of the best rides are considered to be Maxx Force, X-Flight, Goliath, and Raging Bull. We will update with real info asap.

Shedd Aquarium

Widely considered one of the ten best aquariums in the USA, the Shedd sees over 2 million visitors annually due to its reputation and prominence on the Chicago City Pass. The highlight of the park is a 90,000-gallon tank that lends a 360-degree tour of an underwater reef community. Over 70 species glide through the circular tank.

The Shedd Aquarium is definitely one of the best things to do in Downtown Chicago.

Frank Lloyd Wright House

Frank Lloyd Wright is our nation’s most famous architect. That may not sound like a big deal now, but in his day he was a celebrity of scandal and high regard. It is here in Chicago that he built his first personal residence in Oak Park at the age of 22. Along the same street he built a half-dozen other dwellings, as well as the Unity Temple, his best public work in the city of Chicago.

Frank Lloyd Wright geeks will not want to miss this!

Navy Pier

Navy Pier rambles onto Lake Michigan north of the Chicago waterfront. Stretching 6 city blocks and seeing 9 million annual visitors, Navy Pier is considered one of the best things to do in Chicago. Most popular activities include the Chicago Children’s Museum, speed boat tours, a ferris wheel, and plenty of eating and shopping.

Is Navy Pier a bit overrated? We’ll let you decide.

Could-Do: Things to Do in Chicago

Could-Do attractions are worthwhile, but we don’t strongly recommend them for one reason or another.

Montrose Point Bird Sanctuary

Seven miles north of the Chicago waterfront is a strollable prominence called Montrose Point (MAP). You don’t have to like bird watching to partake scenic views of the city and Montrose Harbor, however if you’re into birds there are some wooded trails to view fowl things.

Bahai Temple

Twenty miles north of Downtown Chicago is a Bahai House of Worship (Temple), one of seven in the world. Guests are welcome to stroll the ground or peruse the first floor. The ornate craftsmanship will blow your mind, as will the opulence in the neighboring communities.

First Ascent Climbing Gyms

There are four First Ascent Climbing and Fitness gyms in the greater Chicago area. Whether you are a first time climber or a bouldering champion, this is a mecca of leviathan proportions.

Day Trip to Milwaukee

Less than 2 hours north is the classic city of Milwaukee. Indulge the Harley Davidson Museum, Public Market, Art Museum, County Zoo, or catch a ballgame at one of MLB’s best stadiums, American Family Field.

Lakefront Beaches

Chicago has some decent beaches for a mid-western city. We recommend the three found just north of Navy Pier: Ohio Street Beach, Oak Street Beach (our favorite), and North Avenue Beach at Lincoln Park. Here’s a MAP.

Chicago Museum of Science and Industry

Part of Chicago’s embarrassment of league leading museums, the Museum of Science and Industry has an assortment of dynamite exhibits. Consider the following: A full-size coal mine; a German WWII submarine; a stainless-steel diesel steam train; as well as features on the human body, computers, and other interesting things.

Peggy Notebart Nature Museum

The Peggy Notebart Nature museum is known for its live butterfly house, which is attached to a laboratory and program to study and enhance native Chicago area butterfly populations. In addition to the butterflies, other live animals and nature inspired art can be found at this beautiful facility.

An Honest Conclusion: Things to Do in Chicago

The City of Broad Shoulders has a hell of a reputation for violence and corruption. So much so that when we told people we’d accepted a three-month work assignment everyone got nervous for us. “Be careful!” they said over and over, as if we were headed off to war.

So let’s address that first. The city of Chicago knows better than to allow gun violence in the lakefront museum district. The tourism-friendly part of the city is clean and family friendly by enforcement, and you should bandy about this beautiful section of Chicago to your hearts content (maybe just not at night).

Now… there are sections of the city where you have no business going. The South Side is awful — You would be a fool to wander up in there. And why would you anyway? You can tell with a glance that no tourist belongs in those neighborhoods. Want to prove it to yourself? Go to a Chicago White Sox game. We did.

Damn right we did and never again. Read More! For those sitting in the outfield bleachers at Guaranteed Rate Field: The South Side of Chicago is not safe to visit.

North of the city is perfectly great.

Lincoln Park. Wrigley Field. Montrose Point. All of it is fantastic.

If you head north a good 30 minutes from downtown the setting is a perpetuity of parked-out neighborhoods featuring Great Gatsby mansions from another time. This is where the old money lives and you should definitely besmirch their wonderland with whatever it is you bring.

We would be remiss if we failed to mention the people in Chicago are wonderful. We thought they’d be like New Yorkers, but they were more Minneapolis than Manhattan. Not that there’s anything wrong with people from NYC — love you guys. Chicagoans are just more down to earth, that’s all we’re saying.

I could see us coming to Chicago many more times over the course of our lives. The city has a wonderful vibe — we consider it our favorite big city in the USA (tied with San Antonio). We can’t wait to tear into that famous Chicago restaurant scene some day when the kids are on their own and we don’t have to buy them meals they won’t appreciate.

Consider this a two-thumbs up review. That’s how impressed we are with Chicago. We hope you have the same experience and fall in love just like we did.

Thank you for stopping by our website! We are the Hoffmann family, a full-time RV family that has split residence in Seattle, Washington and San Antonio, Texas. We have special needs children that we homeschool, and work travel assignments for the Veteran Affairs Hospital. If you would like to learn more about us, check out our Start Here and Biography pages.

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