Top 20 Chicago:

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.

Bet on a Horse

Bet on a Horse
Picture 16 of 20

Ok, so this one isn't exactly in the city but, if you make the effort, it can be a perfect getaway from the city. The racetrack is in Arlington Heights, which gives you a chance to ride on the Metra. Metra is a commuter train, and you can catch the Northwest Line to Arlington Park from Ogilvie Transportation Center in downtown. General admission to Arlington Park is fairly inexpensive and gives you the choice of sitting on the lawn or on benches. There are beverages and food for sale, and you can also bring your own food and non-alcoholic drinks (if your cooler is large you might be charged). I'm not huge on horse-race gambling, but I sure enjoy the thrill of putting $2 down on a horse and then cheering them on. Even if you don't bet, it is fun to see the races, people watch, and watch the horses being groomed. A lot of events are held at the tracks including family day (very kid friendly) and derby day (wear your fancy hat and drink mint juleps).

 

Helpful Links:

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.