36 Hours in Chicago (Video)

36 Hours in Chicago

After being invited by Dave Mason of Multiple to attend CUSP Conference at the Museum of Contemporary Art, Gavin and I headed down for the conference and 36 hours exploring Chicago.

We got some local recommendations (thanks Pranali!) and after attending the two-day conference, had a day-and-a-half to make the most of the city.

Below you'll find all the places Pranali suggested we visit (based on our preferences), the actual itinerary we followed for a Friday/Saturday, and some pictures from the trip!  But first, here's the video summary...

36 Hours in Chicago Video

Here's a quick video we put together of our Friday/Saturday 36 hour exploration:

36 Hours in Chicago Recommendations

Here are the recommendations from Pranali, based on the fact we wanted some good food, good photos, and to see as much of the city as possible:

View of the skyline at sunset:

View of the skyline at night:

Jazz bars:

Touristy things:







Pizza/Deep Dish:

36 Hours in Chicago Itinerary

We didn't actually get to all of the things on the above list...not even close really.  Here's a rough outline of what we actually did:


  • Stayed in Wicker Park Thursday night
  • Grabbed coffee/breakfast, headed downtown
  • Walked the Riverwalk to the waterfront, explored the marina
  • Walked back through Millenium Park, saw the Bean
  • Grabbed a quick lunch, headed back to Wicker Park
  • Ran, napped
  • Headed back downtown to catch sunset at Museum Campus (next to the Aquarium, specifically)
  • Had dinner at Lou Malnati's
  • Grabbed a drink at a nearby pub
  • Headed to B.L.U.E.S.
  • Called it a night


  • Got up early and headed downtown for sunrise
  • Watched sunrise from the waterfront by Millenium Park
  • Got some empty Bean pictures
  • Grabbed coffee downtown
  • Headed to Wicker Park for brunch at The Bongo Room
  • Packed and headed to the airport for noon

We could have easily fit in donuts, a rooftop bar, and some late night exploring, but had done most of that through the week already.

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