Travel – Chicago, Illinois

Chicago, Illinois – the Windy City. State 5 out of 50 state. (See I haven’t been to too many places at this point but I would have to say Chicago is probably one of my favorites so far. Chicago is a beautiful city that has amazing architecture (both historical and modern) along with many locations for outdoor activities. There are many things to do and you’ll never be bored. You can take a stroll at Navy Pier or hangout at Millennium Park. If the outdoors isn’t your thing, then you can venture to various museums or catch shows at the Chicago Theatre. If you’re into sports, go catch a Cubs or Bears game with the locals.

Travel Tips

  • You won’t really need a car unless you plan to travel outside of downtown. The blue line connects you from O’Hare airport directly to the heart of the city. A ride from the airport into down on the train takes approximately 45 minutes or so and once you’re there everything is walkable if not a short Uber ride away.
  • Buy a 3-day train pass. The locals refer to the line as the “L” but signs also indicate it as the CTA. The pass is really cheap and you’ll find yourself using the train a lot!
  • Use UberPool to save money. Some places were a little out of the way such as Navy Pier so at the time of my trip, a ride from Millenium Park to Navy Pier costed me no more than $5.00 USD.
  • Check the weather! Chicago can have it’s nice days but if you’re going in the winter be prepared for rain or snow!
  • Stay out of the South side. Many locals I talked to say that the area if fairly dangerous so I wouldn’t recommend exploring this side of Chicago.
  • If you have time, take the train up to Milwaukee, Wisconsin. It’s just a 1.5 hour train ride. Unfortunately, this time around I couldn’t fit it into my itinerary.
View from Willis Tower

Places to Visit as a Tourist

What can you do while you’re in Chicago? Here are a few ideas:

  • Millennium Park (Cloud Gate/The Bean is here)
  • Navy Pier (Firework show during the summer)
  • RiverWalk
  • Willis Tower (formerly Sears Tower)
  • Art Institute of Chicago
  • Wrigley Field
  • Soldier Field
  • Water Tower Place
  • Chicago Theatre
  • Magnificent Mile
  • Historical Building Tour
  • Shedd Aquarium
Cloud Gate


Navy Pier

Mat Surfing

  • Tip for “Mat Surfing” is to always call or contact the school ahead of time to see if you are even allowed to take a drop-in class or come by for an open mat session.

On this trip, I was able to visit the headquarter for Carlson Gracie Jiu Jitsu Located at 2778 N Milwaukee Ave, Chicago, IL 60647 (

Note: The school is slightly hard to find since it is located on a 6-way intersection. The easiest way to find it is that it is next to a Gap clothing store.

Upon arrival, I was greeted by Carlson Gracie Jr. at the front desk. He was very friendly and welcoming. He had me sign the waiver, pay a drop-in fee, and directed me towards the changing room.

Something I suggest while visiting this school is bringing sandals or slippers. No shoes are allowed beyond the desk/audience area. You have to be in either socks or slippers the whole time if you’re walking around the school (bathrooms/area around the mats) and of course barefoot on the mats. Showers are also available for you to use after training.

Training Area

Unfortunately, Professor Carlson Gracie Jr. (most of the students refer to him as Junior) was not available to teach during this class (I was attending the 11am Sunday class on this trip). However, there were several other great instructors around. The class was taught by Anthony and Rudy who focused on stand-up techniques.

The class started with a warm-up session that involved some cardio exercises around the mat. I was then partnered with one of the students, Jugo to drill the techniques.

Carlson Gracie Headquarters

To highlight what was taught for BJJ practitioners reading this, there were drills for breaking your opponent’s posture, a sweep, and a choke using the lapel from standing with a couple variations. After about half an hour of techniques we then proceed to spar/roll. I was able to get in three great rounds with two students and one of the black belts. 

As the class came to a close, we ended with a brief ab workout and called it a day. Great facility and people if you’re looking for a place to train in Chicago! Thanks Anthony, Rudy, Jugo, and Anthony!

The Food

People always talk about deep dish pizza in Chicago but there’s so much more:

  • Giordano’s Pizza (Takes 45mins for a deep dish pizza)
  • Portillo’s Hot Dogs
  • Garrett’s Popcorn
  • Batter and Berries
  • The Purple Pig
  • Girl & the Goat
  • Smoque BBQ
  • Quartino
  • Pequod’s Pizzeria
  • Xoco
  • Wildberry Pancakes and Cafe
Giordano’s Pizza


Chicago is a city that I would definitely like to revisit sometime in the future. The food is great, the art is amazing, and the people are friendly. Another thing that I enjoyed were the street musicians at the train stations. There’s a lot of talent in Chicago (especially Washington station) so keep your eyes and ears open for some great music.

Chicago, Illinois – September 2016

– BJJBug

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