Digital Detours: Chicago Edition

In July, I took a short trip to visit my best friend in Chicago. She had moved back to the Windy City and although I did not want her to leave New York, I was happy to travel to one of my favorite cities. We came, we saw, we conquered and we ate and drank along the way.

72 hours is never enough time to see everything that Chicago has to offer. Thankfully, this was my third visit, so I have already seen some of the fantastic things that make Chicago so great. My best friend lives 20 minutes north of the city, so we took the train on Saturday afternoon to kick off the trip.


The Chicago River is a wonder in itself; we stopped to take a picture on one of the many bridges that dot the city streets.

The Wit

First stop? Rose on the rooftop at The Wit. This is where I fell in love with sparkling rose.


My best friend had booked an Architectural River Cocktail Cruise for 6pm that night. It started to rain at 5:55pm. They said they would go out on the river rain or shine, so we threw the ponchos on, grabbed a beer and settled in for the 90 minute ride.


The rain tapered off for a bit and we were able to take some fantastic pictures of the heart of Chicago. This photo was before the real storm blew in…


If you can’t tell, we are soaking wet. Shortly after the last photo, a crazy storm lingered for the last 40 minutes of our 90 minute river cruise. We sat outside at first, thinking, “This too shall pass…” and pass it definitely did not… we were sopping wet, but our lungs were full from laughing so hard and our heads buzzed from the beers we drank along the way. We took shelter in the bathroom of the boat, along with eight other people. It was an experience for the books.


On Sunday, Jamie took us to Navy Pier where we sampled the local beer and walked from one end to the other. This was at the very end of the pier and we quickly found out why they call Chicago the Windy City.

Check out my other post, 9 Chicago Landmarks You Must See! to see what else we did on our short trip!

  • Chicago looks like such a nice city to visit. Looks like you had a great time!

  • Looks like you guys had a great time in Chicago! Such a fun city. It’s great when you have friends in fun places to visit. Beautifully Candid

    • Thanks! Such a great city – and her suburb was so picturesque!

  • Looks like you had so much fun in Chicago (even if it was a little wet)! My younger sister is moving there next month and I’m really excited to visit because I’v never been. Whenever I do go see her, I will absolutely have to check out this Architectural River Cocktail Cruise!

    Lexi, Lex Be Livin’

    • She’s so lucky! Such a great city! And that river cruise was fun (even in the pouring monsoon!) but I bet it’s especially pretty in the fall!