City Guide: Chicago

I’ve recently spent a few days exploring the wonderful city of Chicago. Yes, I know many of you may say that it was wonderful because I went during the summer and, though that may be true for some, I believe it must be magical in the Winter, cold and all.

I've traveled quite a bit this year and I really want to start showcasing more cities & things to do, so I’ve decided to start posting a quick trip update/city guide every time I visit a new place. I've incorporated in this blog some spots I visited this time & my last time in Chicago! I hope you enjoy.

Chicago, is located in the Midwest, for those of you who may be geographically challenged like myself. It’s in the state of Illinois and is located right off Lake Michigan, which in my opinion, is a win. During the summer you can find people swimming, laying out, ridding bikes, having cook outs, exercising, and basically doing any physical activity you can think of. After getting the weather scoop from conversations with locals, I've been told that the perfect time to visit is between June-September (if you want to avoid feeling the cold). The winter weather starts slowly making it’s way in during October but doesn’t fully arrive until closer to November. Well enough about weather, let’s get to the important stuff!

Chicago has a wide variety of different foods which makes eating your way through the city, so much fun! Don't worry though, you have the ability to walk everywhere which, in my opinion, helps balance it out. Here are a few of the places I visited and loved.

  • The Allis-So Ho House: The brunch menu was filled with so many delicious options that I had trouble choosing. I went with their breakfast pizza and it seriously was AMAZING!
  • 3 Arts Club Cafe: This beautiful restaurant is located in the middle of a Restoration Hardware. The concept is super cool because you can grab a drink while touring the rooms, have a coffee on their comfortable couches, or do brunch/lunch. p.s. If you are looking to share something I suggest the burger; it’s huge and looked delicious. 
  • Maison Marcel: A cute little French bakery with almond milk lattes. The inside is pleasing to the eye, and I would suggest stating that you are there to have a meal since most of the seating inside is reserved for that purpose. We went for a small baked good and a coffee, which was the best croissant of my life…no joke! 
  • BeatNik: This spot has a very cool/bohemian vibe. It's all around a cool spot that you need to see even if you don't stop for a drink.
  • Pequod’s- You can’t go to Chicago and not get deep dish pizza. The first deep dish I had was at Lou Malnati, which after leaving, I wasn’t impressed. I decided to give deep dish one more shot and Pequod’s did not disappoint. I will forewarn you not to come starving. You will have to wait to be seated and then each deep dish takes about 40-45 min to make. Come when you start to feel a tad hungry so by the time it arrives you are ready to grub.
  • Au Cheval- This place is famous in Chicago for it's burger. The wait can be a bit long but it's worth it. I recently found out that there is a Small Cheval which is another location that has recently opened near Old Town. Check it out & maybe the line will be shorter. 

The architecture of Chicago is simply breathtaking. From every angle you will see an amazing view of the city. Here are a few spots that I believed captured Chicago, beautifully. Some of these spots also happen to offer some delicious drinks and prime people watching.

  • Cindy's Rooftop: This rooftop bar offered a spectacular view of the city & bean, plus you can try a frośe popsicle.
  • Drum Bar: It's a rooftop bar located on the top of a boutique style hotel, with a relaxed atmosphere.
  • The Hancock: You can wait in line at the observatory or you can go to the lounge room on the 95th floor of the Hancock to get the same view without paying.
  • The Riverwalk: There are multiple drinks stops along the Riverwalk. I highly suggest buying a drink and enjoying people watching/great conversations.
  • Lake Shore Trail: I suggest renting a bike and riding along side Lake Michigan. It's beautiful and the breeze feels amazing!
  • London House: This rooftop has a phenomenal view of the river walk & the cities architecture.  

Here is a list of things I did in Chicago that are a must. There are a ton of things to check out, and I encourage you to find what it is that you love.

  • Visit Lincoln Park Zoo (free)
  • Go watch a Comedy show at Second City
  • Go see Wrigley Field 
  • Go to a brewery (Forbidden root)
  • See "the Bean" and it's right by Millennium Park 
  • Take a stroll through Wicker Park/Lincoln Park to see all the beautiful houses
  • Eat a Doughnut at Stans or Firecakes
  • Take a walk and get lost in the city. You will find so many awesome things just exploring
  • Rent a bike & bike down the shore/throughout the city. 


  • La Colombe: a unique take on coffee and it's so good. Try the "Pure Black & Tan," you'll love it. 
  • Colectivo: An awesome coffeeshop with outdoor seating and delicious coffee.
  • wormhole: A time machine coffee shop. The atmosphere is retro and super relaxed.
  • Fremont: $5 make it your own way Moscow mules.
  • Heritage Outpost: A very friendly bike/coffee shop with a quiet atmosphere.
  • Sawada Cofee: Super cool vibe and it's owned by a guy who is known for his latte art.

Well, I'm off to plan my next adventure & I know I'll be back to Chicago again so I may add more later! I hope this blog was helpful and if you have any questions regarding Chicago, let me know! 

Safe travels,

Scott Perez