Chicago gets a bad reputation for having the country’s highest crime rate to severe winter weather. If you take away those two caveats, Chicago is an awesome city. A Midwest melting pot full of culture and life.

The Windy City will hit you with its industrial yet modern architecture, incredible selections of food, to its esteemed sports fanbases. Chicago has everything that New York and California have, minus the ocean. That’s not to say Lake Michigan is no ocean, it is.

What makes Chicago special in my opinion starts with the city’s infrastructure and design. Like New York City, Chicago gives you an old and rustic nostalgia of the industrial revolution.

When taking a city tour, I learned that Chicago had a building boom thanks to the Chicago Fire of 1871 that destroyed more than half of the city. This drove the city to reinvent itself building an elegant skyline.

Chicago will not compete with NYC for the tallest skyline, but it does not have to. Chicago has an own identity that cannot be matched.

When traveling to Chicago you will immediately notice that transportation is a delight. The heart of the city lies in “The Loop”, the center of Chicago’s business and commerce. From O’Hare International Airport, you can hop on one of the “L”, elevated subways that will directly take you to “The Loop”.

Being from Los Angeles, I envied how easy it was to travel across Chicago’s neighborhoods. Although the “L” is an old system, it is extremely reliable making Uber and cars pointless in your visit. This will incentivize you to fully experience Chicago’s amazing nightlife, without breaking the bank on Uber.

Being in Chicago for five days, I learned quickly that the city is restless at night. Yes, Chicago has plenty of attractions to see during the day like taking a water taxi across the riverfront or walking down The Magnificent Mile historic theaters and shopping malls. But Chicago is truly a nightlife city.

Tourists and locals have countless opportunities to socialize across the city’s wide range of activities. If your hungry, Chicago has fine and cheap dining down.

The critically acclaimed dish Chicago is recognized for, is deep dish pizza. Deep dish itself is a dining experience, not a fast grab-n-go. You will wait roughly 45 minutes until you feast on a pie because Chicago deep dish is not pizza. It is a pie.


I recommend you try two of Chicago’s renown pizzerias, Lou Malnati’s and Pequod's. If pizza is not your style, you will have many options of delicious meats to choose from. Chicago is known for their butcher shops, a practice that complements great restaurant and gastropub menus.

Visit Fulton Market, located west of the loop with restaurants like The Publican, a pork and beef centric menu with some creative seafood dishes will give you a sample of Chicago’s love for meat. If you are a vegetarian, sorry you always got Yelp.

After feasting on something delicious, you can navigate around some amazing bars scattered across the city or see a live act at The Chicago Theatre. If you are game, go see one of Chicago’s professional sports teams live.

Chicago is a true sports town. From likes of the Chicago Bears in the NFL, Cubs in the MLB, Blackhawks in the NHL, to the Bulls in the NBA. Chicago is basked with historic franchises and fans that truly care about their team’s status.

Chicago makes for an amazing trip. The city has this modern energy found in an old setting. I truly loved Chicago and foresee myself moving out there one day.

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