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Best Things to Do in Chicago, Illinois

Chicago, Illinois, is one of the most storied and legendary cities in the world. Frequently ranked as one of the best large cities to visit in the US each year and considered the second most beautiful metropolis next to Prague, Chicago attracts around 58 million tourists annually. Isn’t it time you were one of them? Here are the best things to do in Chicago.

The Art Institute of Chicago

Let’s start off with one of the city’s most popular locations, The Art Institute of Chicago. Located in downtown’s Grant Park, The Art Institute stretches just under 1 million-square feet, making it the 2nd largest art museum in the United States. Almost 2 million art lovers and tourists pass through it’s patinaed lions and ascend its steps every year to take in the collection and hear the stories that these works have to share.

The Art Institute houses more than 300,000 pieces in permanent exhibitions, with items ranging from the iconic Nighthawks and American Gothic to stone sculptures from the Aztec civilization. There are works and pieces spanning 5,000 years of history from every continent,  from some of the greatest western artists that even the most casual of museum-goers should know, to African tribal objects, Ancient Greek pottery and coins, Japanese woven silk, and so much more in between. The Museum also hosts over 30 special exhibitions each year, so it’s always a good time to visit. And given its size and grandeur, you might need to visit twice.

The Second City

What do Dan Akroyd, Bill Murray, Stephen Colbert, Tina Fey, and Amy Poehler have in common? Besides being really funny people, they all share ties to The Second City. This legendary comedy and performance club opened its doors over 60 years ago and has been splitting sides and launching comic careers ever since. The club launched so many of the biggest names in TV and cinema comedy and is likely one of the reasons films like  “Blues Brothers” and “Ghostbusters” got made.

Besides its historical value, The Second City is an unmissable destination for comedy lovers to catch a show. While The Second City does offer scripted sketch comedy, the club is best known for its “Yes, and…” improv comedy. Check out their website and plan ahead because there are jokes and performances not to be missed. And who knows, you might even get a glimpse at the early careers of the next big names in comedy.

The Forge: Lemont Quarries

Located just 22 miles from downtown Chicago is The Forge: LeMont Quarries, described as “The Largest Adventure Park in the US.” The park stretches over 300 acres and is filled with just about every adventurous activity you could hope for. And unlike so many other outdoor activities, Lemont Quarries operates in all weathers.

The highlights are the hundreds of rope course challenges for all skill levels, but visitors can also try rappelling, taking a ride on exciting bike trails, playing a game of laser-tag with realistic weapons and haptic feedback, hunting for hidden items in scavenger hunts, and putting their wits to the test in escape rooms. The park also features ice-skating in the winter and over 2 miles of ziplines. There’s plenty to do for every age and any kind of thrill-seeker, so come play at The Forge: Lemont Quarries.

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The Magnificent Mile

If the high life is what you’re looking for, then The Magnificent Mile is the place to be. Stretching 13 city blocks from the Chicago River to Oak Street, The Mag Mile, as it’s known, offers class and glamour with every step. The Mile is home to hundreds of shopping destinations, including the finest department stores, exclusive boutiques, and international brands. The Magnificent Mile is also the center of Chicago’s fine dining scene, with gourmet restaurants and eateries across its length.

If all the dollar bills are intimidating, don’t worry. The Magnificient Mile has a lot to offer the more casual tourist. The cityscape makes for a beautiful walk, dotted with pristine landscaping and iconic seasonal flowerbeds. Being a historic part of the city, there are plenty of landmarks to discover and explore. And it’s even more beautiful at night when the lights come on, especially during the annual light festival.

Visit the Parks

One of the mottos of Chicago is “Urbs in Horto”, Latin for “City in a Garden”. Considering the caliber and beauty of the urban parks in the city, it’s clear they more than live up to the motto.

Millennium Park is one of the most iconic areas of Chicago and is home to the easily recognizable Cloud Gate sculpture, more commonly known as The Bean. This park blends urban beauty and open space with art and activities, offering visitors plenty to see and appreciate as they stroll through. Guests can catch live music, go ice skating in the winter, or just enjoy the trees.

Lincoln Park offers more of a traditional gardens experience. Bursting with nature and vibrant plant life, Lincoln Park offers relaxed paths and shaded areas to enjoy. It’s also home to the Lincoln Park Zoo, which has free admission and gives visitors a glimpse at creatures great and small, from red pandas to mighty apes.

Museum of Science and Industry

If you have a fascination for science and technology, then the Museum of Science and Industry must feature on your itinerary. Stretching over 14 acres of space, the Museum is the largest of its type in the Western Hemisphere and is an unparalleled experience.

A trip to this museum could easily take you 6 hours as you explore, learn, and interact. The gem of the collection is a captured World War 2 German sub that can be boarded. Besides that, there are exhibitions on nearly any area of science; whether it’s a 40 foot tornado, halls of mirrors and mathematics, aviation, coal mining, African and black architecture through history, and so much more. No matter what kind of traveler you are, the Museum of Science and Industry is one of the best things to do in Chicago.

Navy Pier

Extending onto the beautiful Lake Michigan, the Navy Pier is an excellent destination for sun, shopping, and a fun day out. There’s a towering Ferris wheel, swing rides, and mini-golf if you’re looking to play, and the Lake gives you access to cruises, boating, and canoeing.

The Pier also has plenty of options for shopping and dining, with restaurants of all types and a number of stores. Visitors can also enjoy Shakespeare performances, IMAX Movies, the Children’s Museum, or free events in Polk Bros. Park. It’s an iconic attraction of the Chicago waterfront and not to be missed.

Garfield Park Conservatory

If you’re looking for impeccable and perfectly landscaped greenery, then Garfield Park Conservatory must make your list. Referred to as “Landscape Art Under Glass”, thousands of plant species from around the world are grown and displayed here in all of their splendor. Admission is free, and this is an excellent escape from the bustle of the city.

The Garfield Park Conservatory offers outdoor collections and multiple climate-controlled steel and glass rooms that create ideal environments for palm jungles, ferns, desert plants, or flower gardens. And when you’re done wandering, grab a snack in the bistro surrounded by flowers.

The Chicago Outerbelt

Did you know there’s a 210-mile hike that stretches around the entire perimeter of Chicago? Called the Chicago Outerbelt, this extreme hike is a lot like the city itself: a blend of urban and natural elements, making it a unique experience in total. The Outerbelt takes hikers through riversides, wetlands, urban environments, forests, and even rare tall-grass savannah. All within sight of the city!

210 miles is a long way for anyone, so it’s best to see the Outerbelt Alliance website and choose a day trip for yourself, although there are multiple camping options available too. No matter where you go, it will be a unique hike, with animal-spotting potential, and is an excellent way to see that natural side of Chicago that even most residents don’t know about.  

Get the Best view of the city

Chicago is renowned for its urban beauty, and that’s a fact you can appreciate from ground level. But why not take in the sites from above? Way, way above.

The 360 Chicago Observation Deck on the 94th floor of the John Hancock building gives visitors nearly unbeatable panoramic views of the city. Besides amazing scenery in all directions, there’s also Bar 94 for the thirsty, and TILT, a thrill ride that lets visitors lean over the incredible drop.

If that’s not high enough, then Skydeck Chicago is the place for you. Offering views from the 103rd floor of the Willis Tower, experiencing what was once the tallest building in the world, is a must. There’s no TILT, but there is The Ledge, a glass box that juts 4 feet out from the building, with nothing but clear glass between you and the drop. Be sure to take some photos, because you can see for miles in every direction.

Pizza

Yes. Really. Pizza. Sure, we could recommend you check out Sue the T-Rex at the Field Museum. Of course, you can catch a Cubs game at Wrigley Field. But no matter what you do, every day of adventure in Chicago is going to leave you hungry, so why not dig right into one of the city’s most iconic foods; deep-dish pizza.

How you go about this is up to you, but there are plenty of bloggers and influencers that can give you guidance. It’s safe to say that pizza is a big deal in The Windy City, so whether you’re looking for tradition, innovation, the highest-rated, or to support BIPOC pizzerias, there will be options for you. And if you want to cut the guesswork out, then book a spot and come hungry to The Original Chicago Pizza Tour. You’ll take a bus tour through several neighborhoods, sampling slices and hearing stories about the birth and growth of this iconic Chicago mainstay.

Now, what do you think? What are the best things to do in Chicago? And what are you most interested in? Let us know in the comments below, and don’t forget to like the video, subscribe to ViewCation, and hit the bell for notifications. Thanks for watching.

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