12 Great Things to Do in Chicago

As the third largest city by population in the United States, Chicago is a very popular city to visit. Being such a large city there is plenty to see and do.

Here are my top 12 things to do in Chicago.

1. Chicago River

The Chicago River goes right thru downtown Chicago before emptying into Lake Michigan. A walk along the river is a must all year long but especially in the warmer months of the year. On warm days, the combination of the river’s clay bottom, water coming from Lake Michigan and algae give the river an almost tropical color that will have you thinking you are somewhere in the Caribbean and not in the Midwest! Speaking of the color of the water, on St. Patrick’s Day they even dye the water green to celebrate the holiday.

Things to do along the river include:

  • Take a walk or a run along the Chicago Riverwalk.
  • Have a meal with river views – there are restaurants along the river with both indoor and outdoor dining.
  • Have a drink along the river – from regular bars to tiki bars in the summer, it’s the perfect spot to enjoy a drink.
  • Watch the artists along the river – if you are lucky enough, you might be at the Chicago Riverwalk when the artists are out painting. They are really amazing to watch.
  • Take a kayak tour on the Chicago River.

While there is plenty to see and do along the river during the day, I also recommend seeing the river after dark as well. Of course, make sure to be safe after dark, the river can be viewed from spots downtown. The many bridges that cross the river are great spots to grab a great photo.

2. Lake and River Architecture Tour

While you are at the river, you must take one of the Architecture tours. These boat tours are probably one of the most popular tours in the city of Chicago. The city is known for it’s innovative architecture and famous architects that built these buildings. Wendella Boats offers a Lake and River Architecture Tour which I highly recommend. This 90-minute tour will take you down the Chicago River and give you the history of the buildings along the river.

From the river, the boat will go out into Lake Michigan. From here you will get a beautiful view of the Chicago Skyline.

3. Navy Pier

Navy Pier has drawn millions of visitors to the lakefront for over a hundred years. It’s a top family attraction in Chicago offering the following:

  • Shopping
  • Restaurants
  • Parks and outdoor public space
  • Chicago Children’s Museum
  • Amusement rides including the Navy Pier Ferris Wheel
  • Chicago Shakespeare Theater

Navy Pier is a must visit for families with so much to keep both children and adults occupied.

One of the other great things to do at Navy Pier is to take in the views of the city from the Pier. Whether you are on the ground or 200 feet up in the Centennial Wheel, the views are stunning. It also makes for a great spot to see the sunset behind the Chicago skyline.

4. Grant Park

This 319-acre city park has tons to see and do. Some of the most popular things to do in the park are:

  • Buckingham Fountain – One of the largest fountains in the world, its actually twice the size of the fountain at Versailles in France that it was modeled after.
  • Millenium Park – I bet you didn’t know that Millenium Park is actually part of Grant Park as opposed to being its own separate park. I actually wasn’t aware of this myself until my second trip to Chicago. This is where you can see one of Chicago’s most well-known sites: Cloud Gate or more popularly known as The Bean. Millenium Park also features pieces of art, fountains and spot to hear live music and watch movies outdoors.

5. Willis Tower

The 110 story Willis Tower opened in 1973 as the Sears Tower and for 25 years it held the title of tallest skyscraper in the world. Located on the 103rd floor of the building is Skydeck. This observation deck is the perfect spot to get great views of the city. If you are daring enough, you can experience The Ledge. This glass box extends out 4.3 feet from the building to give you a bit of a different perspective of being 1, 353 feet above the ground with just glass beneath your feet. While I am not brave enough to try it, more than 1.7 million visitors each year do, so it’s obviously completely safe. Have you/will you try it?

6. Lincoln Park

On the north side of the city, along Lake Michigan, is the 1,208-acre park that was named after former President Abraham Lincoln. The park consists of multiple sports fields and a conservatory. But the main attraction is definitely the Lincoln Park Zoo. The zoo opened in 1868 and is the only privately managed free zoo in the United States. Since it’s free it makes for a great activity for families visiting Chicago.

Lincoln Park is also a great park to just take a walk and check out the views of the skyline from the north side of the city.

7. Wrigley Field

Also located on the Northside of Chicago is the second-oldest baseball stadium in the US, Wrigley Field. Built in 1914, it was called Cubs Park until 1927 when it was bought by William Wrigley Jr. of the Wrigley chewing gum company and renamed Wrigley Field. One of the most unique features of Wrigley Field is that until 1988 it did not have lights which meant all games at Wrigley Field were played during the day even the midweek games. As someone who grew up attending games at the historic Fenway Park, I highly recommend seeing a game at such a historic stadium like Wrigley Field when you visit Chicago.

8. Chicago Tribune Tower

The Neo-gothic skyscraper on Michigan Avenue was built in the 1920s. The Chicago Tribune held a design competition to find the architect for the building, with the winner not only getting to design the building but also winning $50,000 which as we all know was a lot of money back in the 1920s. One of the most interesting aspects of the tower is the bricks from historic sites and events around the world. These bricks were brought back from Chicago Tribune correspondents in their travels covering news around the world. As a traveler, I really enjoyed seeing all these. bricks from around the world.

9. Chicago Theatre

There is no better place to see a show than in a historic theater and the Chicago Theatre is no exception. Opened in 1921, the Chicago Theatre was the first lavish movie theater in the United States. The theater has many French influences, the exterior features a small replica of the Arc de Triomphe in Paris and the lobby was modeled after the Royal Chapel at Versailles.

While they started with playing movies here, they now have everything from concerts to comedy shows to children’s shows. They do also offer tours of the historic theatre although from what I’ve read, these are still on hold due to the pandemic.

10. Chicago Cultural Center

If you’re looking for somewhere to experience culture and architecture, then head to the Chicago Cultural Center. This beautiful building is located downtown and is on the National Register of Historic Places. At the Chicago Cultural Center, you can experience the following:

  • Art Exhibits by local and national artists
  • Concerts by local artists
  • Film Screenings
  • Dance shows
  • Workshops for both adults and children
  • Architecture including the Tiffany stained glass dome ceiling that is definitely a must see.

And the best part, admission to the Chicago Cultural Center is completely free.

11. Drinks at the Signature Lounge at the 96th

One of my favorite things to do when traveling is checking out the view of a city from above. I mentioned the Willis Tower earlier which has great views, but how about enjoying a drink with a view? 875 North Michigan Avenue features the 360 Chicago Observation Deck on the 94th floor. A floor above that is the restaurant, Signature Room at the 95th. And above that on the 96th floor is the Signature Lounge at the 96th.

The views from the Signature Lounge at the 96th are stunning. There is even a great view from the ladies restroom, sorry guys, you don’t get the stunning view from your restroom. In my opinion the lounge is the perfect spot to relax in the afternoon or have some pre or post dinner drinks. In fact, it the perfect spot to catch the sunset in Chicago.

12. Must Eat Chicago Food

One of the great things about traveling is to try the local food. Chicago is a great city for the foodie travelers out there. Some must try foods are:

  • Chicago style hot dogs – These all-beef hot dogs are served in a poppy seed bun and topped with yellow mustard, white onions, green sweet pickle relish, dill pickle spear, tomato slices, pickled sport peppers and celery salt. They are a must try for hot dog lovers. There are many places to try them, one of the more famous is Portillos which has multiple locations throughout Chicago.
  • Deep Dish Pizza – Of all the food in Chicago, this is definitely my favorite! I’m sure most of you have tried deep dish pizza at Uno’s Pizzeria which has locations across the US. While Uno’s has been said to the first place to serve deep dish pizza, I recommend trying Giordano’s while in Chicago. If you want to try lots of deep-dish pizza from different pizzerias, I highly recommend taking a Pizza Tour while in Chicago.
  • Garrett Popcorn – Looking for the perfect snack while exploring Chicago, look no further than Garrett Popcorn which has multiple locations throughout Chicago. They offer regular buttered popcorn and such flavors as caramel, cheddar, nut caramel crisp, buffalo ranch and even the popular Garett mix which consists of a mix of cheddar and caramel.

Chicago should definitely be near the top of your list of places to visit in the United States. With so much to see and do, it’s somewhere you can travel to again and again and still experience something different each time you are there.

For help in planning your next trip and creating the perfect Chicago itinerary, contact Beyond The Miles Travel today.

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16 thoughts on “12 Great Things to Do in Chicago

  1. Great post! Chicago is on my bucket list! I love the idea of a simple meal by the river, that sounds so peaceful and relaxing!


  2. Great guide, gotta save this for when I head over to the Windy City. Definitely gonna try deep dish pizza-just gotta find one that’s halal! Oh and I wanna try this restaurant called Portillos. They apparently make a chocolate shake out of a cake and it looks incredible!


  3. Great guide, gotta save this for when I head over to the Windy City. Definitely gonna try deep dish pizza-just gotta find one that’s halal! Oh and I wanna try this restaurant called Portillos.


  4. A great list, will be saving this for future travels…I love river cruises and the park looks amazing


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