What to See, Eat, and Experience in Chicago

What to See, Eat, and Experience in Chicago

Celebrating a birthday can bring mixed emotions. Let’s be honest, getting older stresses most of us out. My birthday lands on the day after St. Patrick’s Day so I always end up celebrating in green! I have always wanted to take part in one of the biggest St. Patrick’s Day celebrations. This year, turning 29, I decided to GO BIG and book a flight with a friend to Chicago to celebrate with the Chi-Rish! The only emotion my birthday brought this year was pure happiness!

Located on the shores of Lake Michigan, The Windy City is known for good ol’ deep-dish pizza pie, friendly people, and as the birthplace of skyscrapers. If you’re planning a trip to Chicago you’ve got to check out my list of the top 20 things (in no particular order) to see, eat, and experience.


The Bean

1. The Bean

Get your selfie stick ready and don’t worry, everyone is doing it!! Cloud Gate, nicknamed The Bean due to its shape, is a sculpture located in Millennium Park and is a photo-op must when visiting Chicago. For the best pictures get there early to avoid crowds and photo bombers.

While in Millennium Park you can view additional sculptures. In winter months, when the weather permits, you can sip on hot cocoa and enjoy outdoor ice-skating.


Buckingham Fountain

2. Buckingham Fountain

Buckingham Fountain is one of the largest fountains in the world and is a show all its own. The fountain is located in Grant Park on the lakefront with sweeping city views as a backdrop. The fountains water show can be best viewed between April and October, when the weather permits.



Giordano's Pizza Chicago

3. Deep Dish Pizza

A trip to Chicago wouldn’t be complete without a good ol’ deep dish pizza pie! If you’re craving a traditional Chicago pizza pie, try Giordano’s for world famous deep-dish pizza. Another way to find the best deep-dish pizza is to ask a local. Warning: Answers will vary … you may end up wanting to try more than one place!


4. Hockey Game

If this isn’t a true Midwest experience, I don’t know what is. Do as the locals do and bundle up for a hockey game. Check out the Chicago Blackhawks and join in on the cheering and shouting! Go Blackhawks!


Art Institute of Chicago

5. The Art Institute of Chicago

The Art Institute of Chicago is one museum that is well worth checking out. It was voted the #1 museum in the world by TripAdvisor in 2014. Tickets are $25 for adults and FREE for children under 14 years.


 6. “Hop on Hop off” Bus Tours

One of the best ways to start your Chicago adventure is to jump on a “hop-on-hop-off” sightseeing bus tour to explore the city at your own pace. I always love starting my trips on a bus tour to check out the city’s landmarks, acquire some history, and hopefully get the guide’s secrets to the city. Be sure to give yourself a whole day to complete all the stops.

Chicago- River Walk


7. Riverwalk

For a unique experience wander through the city via the Chicago Riverwalk. The river runs right through the city and is lined with skyscrapers on both sides. For two completely different experiences try the Riverwalk both during the day and at night.



8. Lake Michigan

Lake Michigan is the only Great Lake located wholly in the United States as well as the only great lake not bordered by Canada. There are various ways to experience Lake Michigan, my personal favorite is from Willis Tower and the 360 Observation deck.

Chicago Navy Pier

Chicago Navy Pier


9. Navy Pier

Enjoy a day in Chicago at the Navy Pier. You can ride the new state-of-the-art Centennial Ferris Wheel, sip a drink while on one of the restaurant patios, or take a boat tour of Lake Michigan from the Navy Pier.


360-Tilt Chicago

10. 360 CHICAGO – John Hancock Observation Deck

Looking for great city views with a dash of adrenaline? Visit the 360 CHICAGO observation deck and the Tilt experience in the John Hancock building.

The observation deck gives you 360-degree views of the city and Lake Michigan. You can get coffee or a cocktail at the bar and enjoy the view. When skies are clear you can see four states at the same time from one point of the observation deck.

The Tilt experience tips brave viewers at a 30-degree angle over Michigan Avenue. Make sure to hold on tight!

Located at 875 N. Michigan, on the 94th floor of the John Hancock Center, the observation deck is open 365 days a year.

*Travel Tip – Try to schedule your tower visit on a clear day as weather may affect the view.


Signarture Room-Chicago

The Signarture Roon Chicago

11. The Signature Room at the 95th floor of the John Hancock building.

Looking to eat, drink, and enjoy the best views of Chicago? If so, The Signature Room has all three! Located on the 95th floor of the John Hancock building, The Signature Room features white tablecloth dinners, amazing drinks, and views of the Windy City that will leave you wondering if heaven is a place on Earth.

If you’re looking for the views without the formal dining experience, the Signature Lounge features the same amazing vantage points with a more casual feel and a menu that exclusively features drinks, appetizers, and desserts.



Chicago- St. Patrick's Day

Butch McGuire's - Chicago

12. St. Patrick’s Day Celebration

To experience one of the biggest St Patrick’s Day celebrations in the United States, celebrate with the Chi-Rish. Yes, that is a real term. Chi-Rish refers to the blending of Chicago and Irish cultures that takes place during St. Patrick’s Day. The river is dyed green and the city starts off the celebration with a parade. For a true Chi-Rish experience try Butch Mcguire’s bar. You’ll be talkin’ in an Irish accent in no time!

*Travel Tip – To experience all of Chicago’s St. Patrick’s Day celebrations check the events calendar on the City of Chicago’s tourism site: http://choosechicago.com.


Garrett's Popcorn - Chicago

13. Garret’s Popcorn

Mmmmm Mmmm Mmmm! For a mouth watering and warm Chicago treat, try the famous Garret’s Popcorn. I recommend Garret’s Mix. Garret’s Mix was created by local fans and combines sweet caramel and savory cheese flavors. Try both flavors at the same time for a sensory explosion. The employees will mix it right in front of you and customers wait in a line that, at times, wraps around the corner, just to get a taste of this hot deliciousness! Enjoy!


Wrigley Field

14. Wrigley Field

“Take me out to the ball game.” There is nothing more American than baseball and there is no better place to watch a game of baseball than Wrigley. Wrigley Field is the second oldest field in major league baseball and serves as the home of the Chicago Cubs. No games scheduled during your visit? No problem! The stadium offers non-game day tours. I would highly recommend visiting this historical and breathtaking stadium, game or no game.

  Willis Tower-Chicago


Willis Tower

15. Skydeck Ledge Chicago

If you’re scared of heights, this next experience may not be for you. Willis Tower, the tallest building in the Western Hemisphere and formerly known as Sears Tower, invites visitors to literally step out of their comfort zone and see Chicago from a whole new perspective with the Skydeck Ledge.  This experience allows you to step into a glass box 103 floors above the city that extends 4ft out. The Skydeck Ledge features views that rival 360 CHICAGO and an adventure to be remembered!

Location: 233 South Wacker Drive – Chicago, IL 60606

Tip* – Try to schedule your tower visit on a clear day as weather may affect the view.


The Chicago Theatre

16. The Chicago Theatre

If there is one sign that embodies the spirit and style of Chicago, it is the Chicago Theatre Sign. This sign is a photo op must! The colorful landmark is located in the loop, the central business district of Chicago. It can be viewed while on the “hop-on-hop-off” bus or while traveling on foot.



17. Sightsee along the ‘L’ Train

Travel like a local and enjoy the views along the way. Catch the ‘L’ train from the airport and head straight into the city while sightseeing along the way. Catch views such as the Chicago suburbs and Wrigley Field on the elevated train.


Laugh Factory-Chicago

Chicago-Laugh Factory

18. Comedy Club

Q: Why couldn’t the leopard play hide and seek?

A: Because he was always spotted.

If you are like me and LOVE a great laugh you have to try Laugh Factory known as the #1 comedy club in America. Catch a show at 8:00pm or 10:00pm. To save a buck check Groupon for local deals.

Location: 3175 N. Broadway St. Chicago, IL 60657 *Reservations required.

THe Berghoff-Chicago

The Gage - Chicago

19. Bar hop in The Loop

Craving some drinks after a long day in the Windy City? The Loop is the place quench your thirst! This business district is home to world famous bars and restaurants with unique and exciting atmospheres. One of my personal favorites was The Berghoff, a Chicago landmark that serves German-American cuisine and Steins full of your delicious brews. Prost!

Smith & Wllensky Steakhouse, Chicago

Chicago Cut

20. Dine on The River

Skyscraper dinning got you shaking in your boots? If so, try one of the several steakhouses located on the Chicago River for beautiful views that let you keep your feet on the ground. For truly delicious American cuisine, try two of my favorites: Smith & Wollensky and Chicago Cut Steakhouse. The sights, smells, and tastes of these restaurants truly capture Chicago dining.

*Tip – The Chicago Go Card or CityPass is a great way to see multiple attractions on a budget. Depending on the pass, some card options are a great way to skip lines and save time.

Over to you! What are some of your favorite things to see, eat, and experience in Chicago?


One World State Of Mind
One World State Of Mind

Carissa Owens is the travel-obsessed author of travel & lifestyle blog, One World State of Mind featuring travel destinations, tips, food, awareness and photography made with love from around the world.

Find me on: Web | Instagram | Facebook



  1. Melissa
    October 18, 2016 / 6:31 pm

    Take me back ♡

    • carissa
      October 19, 2016 / 4:46 pm

      Can’t wait for our next adventure! Thanks for being a great travel buddy Melissa <3

Leave a Reply

Your email address will not be published. Required fields are marked *