7 Awesome Things To Do In Chicago, USA

7 Awesome Things To Do In Chicago, USA

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In the heart of the United States’ Midwest region is a thriving, urban center filled with some of the world’s best museums, food, comedy, and architecture. With new Michelin-rated restaurants springing up on the regular, and new festivals and comedy taking place weekly, there is never a lack of fun activities to do in Chicago. While you’re here, don’t forget to chat with some locals. You won’t regret it as Chicagoans have been described to be some of the nicest people in the world!

7 Awesome Things To Do In Chicago, USA

Here are 7 awesome things to do in Chicago, USA:

1. View the city from 1,353 feet in the air

The Willis Tower (formerly the Sears Tower and still referred to as the Sears Tower by most locals) is the second tallest building in the Americas (the tallest is the One World Trade Center in New York) and the 14th tallest in the world. It is home to many well-known businesses, including United Airlines.

7 Awesome Things To Do In Chicago, USA

At 1,353 feet (412 meters) high, the Skydeck observation area is the highest observation deck in the United States. The Skydeck is open to visitors 7 days a week and include glass boxes jutting out from the building that offer a clear view straight down from 1,353 feet up in the air. Don’t worry – these glass boxes are built to withstand 10,000 lbs of weight, so you are completely safe standing or even jumping on it!

2. Catch a comedy show at Second City

Second City is a premier comedy club that first opened its doors in Chicago in December 1959. Since then, numerous actors, actresses, and comedians who are well-known today have gone through the program, including Stephen Colbert, Steve Carrell, Tina Fey, Chris Farley, Bill Murray, Amy Poehler, and Joan Rivers.

Today, Second City stands as a comedy club, theatre, and improvisation school. You can catch shows at Second City every night, typically at 8:00 PM or 11:00 PM. If you’re a big fan of improvisation, sketch comedy, or stand-up comedy, be sure to check out the Up Comedy Club, a branch of the Second City that focuses primarily on improv and stand-up. Regardless of which show you end up seeing, you will have a fun night of great laughs, great drinks, and great company.

3. Stroll through Grant Park and catch a concert at Petrillo Amphitheatre

Grant Park is home to several of Chicago’s main attractions, including Cloud Gate (“the bean”), Millennium Park, the Buckingham Fountain, and Chicago’s newest addition, Maggie Daley Park. Open daily from 6:00 AM to 11:00 PM, Grant Park offers visitors and residents 319 acres of greenery, gardens, art, and performance venues.

7 Awesome Things To Do In Chicago, USA

Its largest performance venue, Petrillo Ampitheatre, spans an entire city block and hosts numerous performances during the Chicago Jazz Festival, Taste of Chicacgo, and Lollapalooza. In the summer months, free movies are shown weekly at Petrillo, with over 250 public seats and plenty of seating space on the lawn. In the winter months, head over to the ice skating ribbon at Maggie Daley Park for some ice skating fun with a beautiful view of the skyline.

4. Cheer on one of Chicago’s baseball teams at Wrigley or Cellular Field

The Chicago Cubs vs. White Sox rivalry is a decades old rivalry stemming from the fact that there are two baseball teams in Chicago. It is largely a North Side vs. South Side rivalry, with North Side residents supporting the Cubs and South Side resident supporting the Sox. The rivalry represents so much more than just sports; it is a rivalry over politics, social class, and lifestyle, with loyalty running deep from both sides.

7 Awesome Things To Do In Chicago, USA

To really understand this rivalry and culture, attend a baseball game and talk to the locals. Ask them why they support the team they support and how long they’ve been supporting that team. Chances are, they’ll tell you they’ve been supporting that team since they were born, and their fathers, grandfathers, and great-grandfathers all supported that team as well. Have some beers and hot dogs, kick back, and enjoy not just a sporting event, but a Chicago cultural event.

5. Walk, run, bike, or skateboard along the Lakefront

One of Chicago’s most beautiful assets is its 18 miles of paved trail along Lake Michigan. You can walk, run, bike, skateboard, or rollerblade along the path. On one side, you’ll see the beautiful blue lake, and on the other side you’ll see green parks or skyscrapers.

7 Awesome Things To Do In Chicago, USA

Depending on which portion of the trail you enter on, you may encounter famous landmarks such as the Lincoln Park Zoo, Soldier Field, Museum of Science and Industry, McCormick Place, Grant Park, Monroe Harbor, Navy Pier, and Belmont Harbor. In the summer, bring your swimsuit so you can go for a dip in the water and cool off from the intense summer heat.

6. Visit the Art Institute, ranked the #1 museum in the world by TripAdvisor

The Art Institute of Chicago was ranked the #1 museum in the world by TripAdvisor in 2014 and one of the top museums in the world by TripAdvisor for four consecutive years: 2013, 2014, 2015, and 2016. In addition to its permanent exhibits, the Art Institute offers around 30 special exhibits at all times. Even if you’re not an art connoisseur, you will recognize some famous pieces such as American Gothic, and the variety of art offered guarantees everyone an enjoyable time, regardless of what style of art you prefer.

7 Awesome Things To Do In Chicago, USA

7. Take a walk along Chicago’s newest path, the 606

The 606 is the newest addition to Chicago’s outdoor space and was a decade in the making. The series of trails and gardens comprising the 606 cover an old elevated railroad track that has been left unused. You can walk, run, or bike on the trail, and make sure you take time to admire the artwork as well.

7 Awesome Things To Do In Chicago, USA

Want to take a break or grab a snack? Hop down from the line and you’ll find yourself in the heart of the Wicker Park or Logan Square neighborhoods, where you can find some of the best coffee shops and restaurants in the city.


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Hi, I'm Diana, the big sister in the sister duo. I left my job as an attorney in March 2017 to pursue the work-from-anywhere/travel-everywhere life aka The Dream. I blog about off the beaten trail travel destinations, adventure travel, immersing in local cultures, and publish plenty of travel guides for all you who are too lazy to plan your own trips. I've traveled to 61 countries to date, and some of my recent adventures include hiking Mt. Kilimanjaro, visiting a child I've sponsored for over 10 years in Rwanda, and exploring the Middle East.

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11 Responses
  1. I’ve never been to Chicago, but of all the cities in the US, it is one of three that I would want to explore more. The other two being NY and LA. I like how you’ve added more than just tourist spots in your list. I love to watch standup comedy and going to Second City would be quite high on my list.

  2. What a great compilation. Especially loved the scary picture at the Skydeck observation area. Would want to do one such picture. That lakefront looks awesome too. Great for summers!

  3. Jane Dempster-Smith

    There is so much to do. I am not sure I could do the glass boxes on the Skydeck but would definitely like to walk the 18 miles along Lake Michigan. I did not realise that the Art Institute was #1 world’s museum according to Tripadvisor. This is something I would love to visit. Thanks for sharing.

  4. Cat

    You can’t visit Chicago without watching a baseball game. We do that, as well as visit the Art Institute, when we end up in Chicago.

  5. umiko

    I’ve never been to Chicago, but this post give me ideas on what to see or do while visiting. I think Willis Tower is a #1 must-visit for first timer, followed by the Bean. And I just found out it’s more than a ‘bean’ in that area. And I had no idea that part of the city built along Lake Michigan! That is really an amazing view!

    1. A lot of people miss the bit about Chicago being located along the lakefront, so you are not alone! It does make for beautiful views though, and fun opportunities to play beach volleyball or go for a boat outing in the summer.

  6. Daniel

    It’s been a few years since I last was in Chicago and I forgot just how amazing this city is. I have visited the Art Institute but I never realized it was ranked as the world’s best museum according to Tripadvisor! That’s something new. You sure took me down the memory lane with this article 🙂 Thank you for sharing

  7. Chicago is the first American city that I came to know about as a child even before NYC! That’s because one of the greatest Indian personalities, Swami Vivekananda has a street named after him in Chicago. Nice to learn about the Art Institute of Chicago, that’s a place which would at the top of my itinerary. Next one will be the Willis tower, although, I am already scared seeing you standing at the edge!

    1. I love that Chicago was the first city you visited in the U.S., Sinjana! Thanks for sharing that bit of history too – I’ve lived here for 8 years and had no idea about that!

  8. Abhinav Singh

    I have been to some skyddeck observation areas but this looks exceptional. Despite its strength, I would still be freaked out to stand here. The lakefront looks gorgeous. I would love a leisurely walk here in the evenings. I didn’t know Chicago has so many interesting activities to do.

  9. Yukti

    I am planning for Chicago after a couple of months and what a timely post. Viewing from the Observation deck looks interesting and strolling across Grant Park is also an amazing thing to do here. I never knew that this city has wonderful art institute and also ranked #1 on Trip Advisor. Would definitely check that out too.

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