When I was in 4th grade, my parents took me to Chicago, and I fell in love. I fell in love with the architecture, the people, the food, and the atmosphere. It is a large city, but it isn’t overwhelming. It is crowded, but the people are friendly. The tall buildings and narrow streets can be daunting, but they are full of architectural wonders. The food choices are limitless, and you can’t go wrong. Fast forward 12 years and I was living in Chicagoland. I spent 7 years living in the area and trying to find out all of secrets this city has to share. I checked out the tourist spots as well as the gems hidden in alleys. Life eventually led me away from Chicago (at least for now), but I’ve compiled a list of 20 things that I think everyone should check out. Flip through the gallery to view my top 20 Chicago.
I might be a little biased, but the Chicago skyline is the most beautiful skyline in the entire world. Every building has its own character giving the overall skyline texture, color, and shape. And while the skyline is amazing during the day it really shines at night. I think the best way to view it is from a distance so you can capture the entire skyline. My favorite place is from Adler Planetarium because you are looking across the Chicago Harbor and can see all of the lights reflecting off the water. Insider tip: On the third Thursday of every month, Adler holds a 21+ event called Adler After Dark. You can purchase a cocktail, wander through the exhibits, and then gaze at the skyline while chatting with friends. It is where the locals hangout and one of the most unique ways to see the city after dark.
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1. Bike the Lakefront Trail and end your adventure at Hopleaf Bar.
2. Take an Arch itecture Cruise. I recommend Wendalla and tours from the Chicago Architecture Foundation.
3. See the Buckingham Fountain Light Show.
4. Eat a Chicago dog. Choices include Downtown Dog, Superdawg, and Portillos.
5. Drink Gluhwein at Christkindlmarket.
6. Party at a Cubs Game.
7. Watch the Navy Pier fireworks.
8. Take a stroll through Lurie Garden.
9. Check out Open House Chicago.
10. Enjoy a concert at the Pritzker Pavilion.
11. Splash in the Crown Fountain.
12. View the skyline from Adler Planetarium’s event, Adler After Dark.
13. Take your picture at The Bean.
14. Have a drink at the Signature Lounge.
15. Have a picnic at Ravinia.
16. Bet on a horse at Arlington Park.
17. Attend a festival. My favorites are Lollapalooza, Printers Row Lit Fest, and Chicago Blues Festival.
18. Admire the Lincoln Park Zoo Lights.
19. Watch the Air and Water Show.
20. Relax at the North Ave. Beach.
Disclaimer: We were not paid by any party to write our recommendations.