(+/-) 36 Hours in Chicago

My kind of town: Chicago.


Throughout my lifetime, I have visited Chicago multiple times. To this day, I still can’t get over the beauty  and cleanliness of the city. I recommend every person makes a trip out there at some point.

With my recent visit, I wanted to make sure that old favorite stops and new adventures merged together. The New York Times Travel Section has a weekly article focusing on 36 hours in a given city. Always the planner, any trip I take I must research all the best restaurants, tourist spots and shopping in a city so that I can maximize my time. One of my go-to references for any short visit is the 36 Hour New York Times series.

In homage to the New York Times series, I present my version of 36 Hours in Chicago.


  1. Terminal 3- O’Hare International Airport (ORD), Noon

Make a stop at Garrett’s Popcorn at Terminal 3 and pick up a bag of Garrett Mix combining sweet CaramelMix with savory CheeseCorn. Trust me, having this snack within arm’s reach will satisfy those munchies cravings throughout the next 36 hours.

Start the trip with a snack.
  1. Blue Line-Chicago Transit, 1pm

Instead of taking an Uber or taxi ride into the city, try getting on the Chicago Transit Authority-Blue Line. This subway ride stays above ground most of the way and allows you to take in views of the suburbs and Chicago as you head into the heart of the city. The train cuts through some charming neighborhoods to also give you a great mini-architecture tour. Get an unlimited pass and get riding!

  1. Diner Style-late lunch, 2pm

California lacks diners. In the mid-west and east coast, one can find a diner everywhere. So since you are visiting this city, eat like a local and get some diner food. Skip the salad. You are on vacation!

  1. Allyu Spa, 4pm

When we arrived in Chicago, it was pouring rain. Crazy summer weather. Thankfully we had reservations for a late afternoon massage and shower. Allyu Spa offered us travelers a great, dry location to relax, maybe mediate, unwind and freshen up before an evening of happy hour stops. From my research I found that Allyu is repeatedly listed as one of the best spas in Chicago.

  1. Happy Hour-Everywhere/Anywhere, 6pm

Chicago folks know how to drink. Every bar we drove by seemed to be filled with people. I theorize that Chicago residents are just so excited for the great summer weather that they just want to drink, drink, drink. There will be plenty of bars offering some kind of happy hour special. If not, keep walking. You will eventually find one.

  1. RPM Steak-River North, 8pm

I heard about this steakhouse from watching Giuliana Rancic’s reality show. The restaurant maintains a definite cool, hip vibe.

Cocktails =Great // Dinner=Great//  Desserts=Amazing// Service=A+

  1. Folklore-Wicker Park, 11pm

This Argentine restaurant and bar is a block away from my aunt’s apartment in Wicker Park. A perfect place for a strong drink to end the night. Note, throughout this neighborhood you can find a number of really hip and happening bars. The options are endless.

  1. Eat- Garrett’s Popcorn, Midnight

Perfect late night snack when you are slightly buzzed and just need to munch. Trust me.


  1. Cindy’s Rooftop-Michigan Ave., 11am

I cannot get over the view from this rooftop restaurant/bar. From the balcony, you get an incredible view of Lake Michigan and Millennium Park. A mid-day visit allows you to relax in the mid-day sunlight and enjoy fancy cocktails. Try the desserts. I am not usually a Lemon Meringue person, but Cindy’s makes an amazing version. Question: Is marshmallow a foodie thing that I’m not aware of?

The sun shines differently in Chicago.
  1. Navy Pier, 2pm

A tourist trap but I hear the Children’s Museum here is pretty impressive. From Navy Pier you can buy all your souvenirs and get in line for one of the many city Chicago tours. Warning: Taxis are difficult to flag and Uber/Lyft for some reason isn’t allowed to do pick ups.

  1. River Architecture Boat Tour-3pm

Disclosure: I’m an architect junkie. A tour on a river where you physically see and listen to history about the skyscrapers along the Chicago River? Be still my heart. Chicago really is a magnificent city. What better way to take a moment to soak in its beauty then to ride along the river?

Warning: Chicago heat and humidity is no joke. So be prepared to burn in the sun or better yet maybe try and go earlier in the day.

  1. Briciola-West Town, 6pm

Homemade pastas under trees with market lights in a tiny backyard. It’s all about ambiance and Bricola has ambiance. Chicago also is big on BYOB. Holla!

  1. Division Street- Wicker Park, 8pm

Keep walking down Division and you are bound to find a bar. Chicago folks know how to drink and appreciate outdoor space. Warm summer nights, wine, good company can’t be beat.

  1. Eat- Garrett’s Popcorn, Midnight

Get home from the bar and look for a snack. Ah, popcorn. Finish up the bag while you silently curse your sister for eating all the Carmel flavor and only leaving you with CheeseCorn.

View from Cindy’s Rooftop.


Chicago Athletic Association

For the baller out there, The Chicago Athletic Association is a beautiful hotel in a historic building. The second floor lounge/game room steps you into a different period of time. Oh. And there is a Shake Shack right in the building.



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