1. Having The “Tallest” Tower In The Nation
Willis Tower–which everyone still calls Sears Tower–is better known as the “second” tallest building in the United States. But it if you take the enormous spire off of One World Trade Center, then Willis Tower is the tallest. Chicagoans love to brag that their tower is still bigger than that poser in NYC.
2. Lounging On Oak Street Beach
Whether you’re craving a game of volleyball, a quiet jog through the palm trees or an afternoon of soaking up the Chicago sun, Oak Beach is where summertime action happens. After all, what beats digging your feet into the warm summer sand on a balmy summer day?
3. Watching a Game At Wrigley Field
Baseball at Wrigley Field...does it get more all-American that this? Head over in the spring or summer to catch a Cub’s game in all its glory. And don’t forget to buy a funny hat, chow down on a chilli dog or beat the heat with a brewski or two.
It doesn’t matter if the Cubs haven’t won a World Series since 1908--this stadium has historic charm like no other.
4. Dyeing The River Blarney Green
There are some cities that are proud to have a large Irish population, and then there is Chicago. Every St. Patrick’s Day, the people of Chicago dye the river green and then go to the pub and guzzle green beer. That, folks, is true devotion.
5. Ditching Their Diets For Real Deal Pizza
Chicago’s citizens dig a pizza with chunky tomato sauce, loads and loads of gooey cheese and a deep-dish crust. Oh, and don't forget the multitude of toppings waiting to be slapped on: pepperoni, bell peppers and sausage.
6. Checking Out The Largest Monet Collection In The World
The well-known Art Institute of Chicago houses a permanent collection of Impressionist and Post-Impressionist art, as well as works from Old Masters and American, Asian, modern and contemporary artists. You’ll get lost in their collection of more than 30 Monet paintings, including his famous “Haystacks” and “Water Lilies.”
7. Enjoying The View Of Marilyn Monroe
This enormous statue might not be shaped like a bean, but it’s definitely a landmark that Chicago’s citizens have grown to love. It’s pretty standard to see some adolescents trying to sneak a peak of Marilyn’s undercarriage.
8. Lake Michigan In Any Season
Chicago in the winter is so different from Chicago in the summer, that if you visit during both seasons, you won’t believe it is the same place. Case in point, Lake Michigan.
In the summer, people love to go to the lake and take a relaxing dip, but this past winter Lake Michigan broke a record for ice coverage--93.29% of the lake froze over. Summer or winter, it’s gorgeous.
9. Fabulously Fresh Farmers’ Markets
In recent years, Chicago has gravitated towards becoming one of the most health-conscious cities in the U.S. There are literally hundreds of farmers’ markets in Chicago. There are so many twice-weekly markets that you can find one anywhere in the city.
10. Drinking All The Wine
Chicagoans love wine, and they LOVE the The Windy City Wine Festival. The festival offers wine connoisseurs the chance to sample over 270 wines from around the world. You can learn all you need to know by attending the festival’s expert-led wine pairing seminars
11. Being Indie-Craft Renegades
The annual Renegade Craft Fair is an iconic Chicago event held on Division Street in Wicker Park. This indie-craft marketplace showcases the wares of the many craft makers in the area and puts a spotlight on all things handmade.
12. Having The Crown Fountain Spit On Them
Millennium Park is home to many eclectic structures from well-known artists, such as Frank Gehry’s outdoor concert pavilion consisting of twisted metal towering over 120 feet and Jaume Plensa’s 50-foot tall video projecting water fountains.
13. Soaking Up The Sun At The Navy Pier
Chicago’s most visited attraction used to be a drab slab of concrete protruding into Lake Michigan. After a huge effort to revamp it, the pier stands today as an icon of bustling activity on the waterfront. And Chicagoans love catching free fireworks shows.
14. Their Resident Dinosaurs
Although there are many anthropological and biological exhibits hosted at the Field Museum, it’s Sue the T-rex that has the city’s heart. Ever since Jurassic Park hit theaters, people have been flocking to catch a glimpse of Sue.
15. And The Dolphins
The Shedd Aquarium features more than 32,000 marine creatures, including sharks, giant octopi, sea turtles, beluga whales and dolphins.
16. Kartoffelpuffers
The best way to celebrate Christmas is at the German Christkindlmarket. Chicagoans brave below zero temperatures to come out for this event, and you would too if you tasted Gluhwein and delicious melt-in-your-mouth Kartoffelpuffers (potato pancakes).
17. Lining Up For Good Eats
People of Chicago love good food, and they don’t mind waiting in the cold for it. And the longest lines are always at the annual Taste of Chicago festival which hosts hundreds of local bars and restaurants.
18. Eating Toro Tartare At Japonais by Morimoto
This authentic Japanese restaurant on Chicago Avenue has been on the upswing for the last 10 years thanks to the love for its Toro TarTare. Run by Iron Chef Masaharu Morimoto, the menu has most of the city drooling. Grab a seat by the sushi counter and get a sneak peek at the these experts displaying their dexterity.
19. Having Public Transportation Above Ground
Chicagoans agree that waiting underground for a train is inhumane. Because they enjoy the wind so much, they built the L above ground (until you get on the red line). It’s a simple pleasure to see the sky as you wait for your train after a hard day’s work.
20. Telling Everyone They Know They Saw Obama At Spiaggia
Spiaggia is the only four-star Italian restaurant in the city and a favorite of the President. You might just spot Barack and Michelle grabbing a bite at this upscale joint, which features handmade pasta and wood-roasted meats.
21. Watching Football In A Freaking Blizzard
It’s an understatement to say that Chicago has its fair share of snowstorms. Some of the blizzards that they have to deal with are downright brutal. While other cities would call off their sporting events during a blizzard, Chicagoans party it up.
22. Cycling Along Lake Shore
Chicago is a fantastic city for cycling in general. Thanks to the Bikeway cycling program, this eco-friendly mode of transportation may be a force to contend with in the future. But until that happens, Chicago’s citizens enjoy it as the tranquil activity along Lake Shore.
23. The Bean
That jelly bean is enormous, and everyone from Chicago is proud of it. It isn’t uncommon to hear people say “meet you at The Bean.”
Pro tip: it’s excellent for taking trippy pictures of your reflection, so bring your camera.
24. Spending A Lot Of Time On LSD
No, no, not the drug. I’m talking about Lake Shore Drive, the highway that runs along the city. When there is any bit of traffic, Chicago’s citizens know exactly what to do. They won’t honk, but patiently wait for the traffic to shore up. And that’s doubly true during the winter when it’s snowing buckets!
25. Eating the Sloppiest Of All Sandwiches
Have you ever had a sandwich that required a dozen napkins? Well, an Italian beef sandwich at Portillo’s requires about ten times as many napkins (or maybe an entire beach towel). But despite the mess, the entire thing is so delicious that you will want to gobble your juice-soaked napkins, too!
26. Sampling Authentic International Cuisine At The City’s Ethnic Restaurants
The diversity of the city is evident from the many authentic international restaurants. Whether you’re in the mood for Thai food at PS Bangkok, Serbian food from a corner restaurant, Salvadorian pupusas, Korean food, original Ethiopian cuisine, Guatemalan or German fare, you can find literally anything.
27. Cheering For Michael Jordan Long After He Retired
Move over Lebron, Michael Jordon is the king of basketball and he spent nearly his entire career playing for the Chicago Bulls. When they aren’t watching ESPN classic replays of epic Jordan dunks, Chicagoans are at the stadium watching hard-working Joakim Noah do his thing.
28. Tina Fey Making Them Laugh Their Faces Off
Tina Fey started up her career as a comedian in Chicago at the comedy club The Second City. Dan Akyroyd, John Candy, Stephen Colbert and Bob Odenkirk also spent time eliciting chuckles here.
