Why Chicago, despite it's flaws, is still one of my favorite cities anywhere in the world. But, before you pack you bags and head to the Windy City, I spill the secrets of Chicago... telling you the good, bad, and ugly.

0:00 Introduction
0:22 Skyscrapers
1:42 Architectural Boat Tour
2:43 Unpredictable Weather
3:30 River Walk
4:35 Chicago Food Scene
5:42 Fulton Market District
6:27 Jenni's Ice Cream
7:03 Expensive City
8:00 Loud and Noisy
8:38 O'Hare International Airport
9:14 Second City
10:02 Chicago Parks
10:58 Conclusion

First, you should know that Chicago is all about skyscrapers. It's the birthplace and epicenter of skyscrapers, with a rich history and a stunning skyline. Even though other cities may have more or taller skyscrapers, few match Chicago's architectural significance.

To see these skyscrapers, there are many great vantage points, like Grant Park or Michigan Avenue near the John Hancock building. However, if it's your first time, you must go on an architectural tour. These 90-minute tours take you along both branches of the Chicago River and are very educational, offering unique stories about each building. I recommend the tour sponsored by the Chicago Architecture Center because it uses smaller vessels, which are less crowded. This might cost $5 or $10 more per ticket, but it's worth it for a more comfortable experience.

One thing I don't love about Chicago is the unpredictable weather. Winters are freezing, and summers are extremely hot. Spring and fall can have decent weather, but it's still unpredictable, often changing hour to hour. The lake effect means you could see a clear forecast, only to be rained on or hit by a windstorm later.

On a positive note, Chicago has developed its Riverwalk beautifully over the years. Inspired by San Antonio's River Walk, the South Bank of the Chicago River now features shops, restaurants, exhibits, and a Vietnam memorial. It's a great place to explore both day and night, offering a lively vibe and plenty to do.

Now, let's talk about food. Chicago is one of the best foodie cities in the world. You can't miss the deep-dish pizza. I recommend Lou Malnati's, a local chain with around 50 or 60 locations in the greater Chicago area. They serve delicious deep-dish pizza, and my wife swears by their salads, too. Another must-try is the Chicago dog, a hot dog with onions, peppers, tomatoes, pickles, and mustard, but never ketchup. You can find these almost anywhere in the city.

If you're looking to venture out of downtown, head to the Fulton Market District. This trendy area has lots of restaurants, including the unique Chinese restaurant Duck Duck Goat, which I highly recommend. Another cool spot is Time Out Market, a trendy cafeteria-style eatery with about a dozen different restaurants.

For breakfast, check out Stan's Donuts, famous for their cruffins, a mix between a croissant and a muffin. And don't miss Jeni's Splendid Ice Creams, especially their brown butter almond brittle flavor. This place often has a line out the door, which is a good sign.

Another downside of Chicago is its expense. Hotels, parking, and Uber rides can be pricey. The sales tax rate is over 10%, which adds up quickly. Dining out can also be costly, with some places including gratuity and additional surcharges.

Chicago is also a loud city, with noise from emergency vehicles, motorcycles, and the L train. The sounds bounce off the buildings, making it noisy even in hotel rooms facing main streets.

O'Hare International Airport is often critiqued for being congested and busy, with traffic jams to and from the airport. However, it offers many dining options and flights to almost anywhere in the world. With an $8 billion revamp in progress, it could become one of the most modern airports by the end of the decade.

One must-visit in Chicago is The Second City, a world-renowned improv comedy club in Old Town. Many famous comedians, like Bill Murray and Tina Fey, started here. They have phenomenal shows every night, and you can even catch an afternoon show on weekends if you prefer not to stay out late.

Lastly, Chicago's parks are legendary. Grant Park is the city's "front lawn," with the beautiful Buckingham Fountain and ample space. Millennium Park, in the northwest corner of Grant Park, is home to Cloud Gate (the famous Bean). Lincoln Park, on the northern end of town, offers a huge green space along Lake Michigan.

Despite its flaws—expense, noise, unpredictable weather, and some violent neighborhoods (not in tourist areas)—Chicago remains an impressive city. The architecture, parks, food, and vibrant culture make it a place worth visiting. Even with its challenges, Chicago is one of my favorite cities, and I'm sure you'll be impressed if you give it a chance.