The 20 Best Things to Do in Chicago

The 20 Best Things to Do in Chicago

Heading to the Windy City? Looking for the best in a Chicago experience? Well, enjoy your trip and take the following as a fantastic guide to getting that true, authentic "Chicago Experience".


1. Micacle Mile

No trip to Chicago is complete without a stroll up and down the Miracle Mile. Enjoy boutique shops, exquisite cuisine and authentic Chicago style pizza all on this cherished and legendary street.


2. Cloud Gate

Head over to Cloud Gate and take in the amazing architecture and sculptures. Grab some lunch and sit while taking in all the beautiful artwork.


3. Travel in Style

Rent a limo and take in a concert where the locals go at the Jay Pritzker Pavillion. Check out the schedule for who is playing, then enjoy an outdoor concert, Chicago style.


4. Go up the Willis Tower

No true Chicago experience is complete without a trip to the Willis Tower and the observation deck. Amazing 360-degree views of the city and the lake are here so bring the camera. 


5. Head to Navy Pier

A trip to the Navy Pier makes everyone happy. Here you have the famous ferris wheel and other carnival like delights. Locals and tourists alike love the Pier.


6. Take in Some Culture

If you think only New York City has great art museums then you need to be sure and go to the Art Institute of Chicago, which gives MY and Paris a run for their money.


7. Try the Local Food

Gastronomes need to be sure and try three things when in Chicago: Chicago deep dish pizza, Chicago Italian Beef Sandwich and the Maxwell Street Polish food offerings. 


8. Watch a Baseball Game

Love 'em or hate 'em, if you go to Chicago during baseball season, you have to go to a Cubs game at good ol' Wrigley Field. This is almost a shrine to baseball and is a not-miss.


9. Visit the Harpo Studios

See where Oprah, one of Chicago's favorite daughters, got her start. Oprah is as much Chicago as the Sears Tower and a trip to Harpo is a Chicago must-do.


10. Beaches

Head over to Montrose Beach, rent a kayak and enjoy a paddle along Chicago's waterfront. This gives a great and fresh perspective to the city.


11. Bike Ride

On those lines, rent a bike and tour the city with the free maps for cyclists. This gives you a chance to be an active participant in the city as you enjoy your trip.


12. Tour The University of Chicago

Find not all Ivy League quality schools are in the east. This University has been home to numerous icons of history and is a true Chicago experience.


13. American Football

Once more, sports fans need to catch a Bear's game if you visit Chicago in autumn. Grab a brat and a beer and settle in for a raucous good time.


14. Enjoy a Festival

If you time your Chicago visit for mid-March, be sure you go to the famed Chicago St. Patrick's Day Parade. Be sure to check out the river as it is colored green for the day. Channel your inner Irish with this truly Chicago take on St Patrick's Day.


15. Join a Parade

Speaking of parades, the Gay Pride Parade in Chicago has become one of the biggest in the USA. Be sure to show your support for a real Chicago stand!


16. Pubs

Chicago is home to some truly enigmatic and fun pubs. No trip to the city is complete without checking out some of the best, like Galway Bar. This is a real experience and gives Chicago vibes all over the place. Have a pint and a shot like the locals.


17. Weiner Circle

Drop the best $20 you will ever spend at The Weiner Circle and order a chocolate shake. Yes, a $20 shake that is beyond belief and is the real Chicago.


18. Dinner Crawl

Go to Andersonville's annual dinner crawl to get a taste of every type of cuisine offered in the city. This yearly event is a real Chicago tradition and a tasty one at that.


19. Transport

Ride public transit and experience and "El" or "elevated Train". These take you all over there city and are as ubiquitous to Chicago as cold winters.


20. Gershwin Tunnel

The Gershwin Tunnel that connects terminals C and B at O'Hare airport is a real experience, and one that is almost like being in a science fiction movie. Start your trip here if you are flying into the city.


As you can see, there is something for everyone in Chicago, and all varied and delightful.



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