The Windy City for the Win

In a city known for cosmopolitan flair, local experiences can be the best. Chicago is known for its high rises, sports teams, and economic machine. Downtown Chicago is a sure bet for many fun things to do including Navy Pier, shopping at Water Tower Place, or eating at one of the city’s many restaurants. Sure there is a lot of business in this city. But, if you venture away from downtown, you’ll see why Chicago is known as a city of neighborhoods.


Anchored by the Center on Halsted, Boystown is one of the most vibrant LGBTQ neighborhoods in the United States. They throw one heck of a Pride Day Parade, and their Market Days are sure crowd pleasers. This is one Chicago neighborhood where the nightlife is the talk of the town. So be sure to take a mid-day nap, or prepare to sleep on the return flight home.

Also known as Northalsted, this area has amazing shopping. You’ll find everything from vintage clothing (aka thrift shops), to high-end boutiques. Shopping here is on point and plentiful.



Experience one of Chicago’s liveliest and most entertaining neighborhoods when you visit Lakeview. With the amazing shoreline of Lake Michigan to the east, and Lincoln Park to the south, this part of Chicago has something for everyone. Bars and pubs are an integral part of the local flair of neighborhood life. Peppered in between are opportunities for shopping at nearby boutiques, eating at world famous restaurants, and experiencing culture.

Oh, they have culture galore. Just visit the Belmont Theater District with over 20 different performing arts companies. There are many festivals that take place throughout the year in the Lakeview neighborhood. Chicago is also known for its live music, and there are many venues where you can take in the local music scene.



It’s not every day that a baseball park gets a neighborhood named after itself, but if you are a grand ballpark like Wrigley Field you deserve it. This neighborhood is a sport and bar mecca, as you would expect it to be. It is going through a bit of a renaissance of late due to the Chicago Cubs winning the 2016 World Series, their first in over 100 years. You’ll see a true slice of America when you visit this neighborhood off the beaten path.