Chicago Itinerary #alynbricityspree

My sister and I had the best time in Chicago this year for our annual sisters trip. I thought I'd share a bit about our itinerary before I share what I packed and wore. Here's how the trip went: 

Thursday | Arrive in Chicago
We arrived on Thursday night and headed straight to the apartment where we'd be staying. One of my college roommates lives in Chicago with her husband and they were out of town (in Peru!) so they let us stay at their place. It was the cutest apartment in Wicker Park and was such a great hub for us. More importantly, she had sent me a list of favorites around the city (primarily food/drink) which really helped us plan the weekend. We started things off with a late dinner at their neighborhood fave, Folklore

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Friday | Tourist Day
Friday started off with breakfast with another college roommate and her adorable daughter. After that, we walked around downtown (making a quick stop at Kravet/Lee Jofa so sissy could do some research for her job in Portland) and then hopped on the River Architectural Tour. We got so lucky with the weather - the sun came out and we had a warm ride through the city learning all about the famous buildings that make up the skyline. 

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After that we grabbed a quick bite before heading out to Oak Park to see the Frank Lloyd Wright Home + Studio and walk through the hometown of my college bestie. 

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The night wrapped up with dinner at Nellcote where we sat outside and enjoyed the sights of everyone out to dine in the West Loop. 

Saturday | Roaming + Second City
Because we had lots of booked things on the schedule for Friday, we left Saturday open to just wander the city. We walked through some of the buildings we'd seen on the architectural tour, stopped by the bean (cloud gate), and made our way through Navy Pier. 

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Then it was back to the apartment to get ready for our big night at Second City. We had tickets to the late show, so we decided to splurge and do the tasting menu at Salpicon beforehand. The food was incredible, we ate WAY TOO MUCH, and then had to practically run down the street to make it to the show in time, where we shared a bottle of champagne and laughed long into the night. 

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Sunday | Departure
Sunday we had a bit of free time in the morning before heading home so we headed back into the city for some donuts and one last walk around town. 

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We spent some time on the flight home brainstorming other cities we want to visit together. Lots of cities made the list: some that I've already been to for work, like New Orleans and Austin; some that neither of us have visited, like Charleston; some that we've been to together, like Boston; or we may just pick somewhere that we can visit family, like Denver. Time will tell where the next #alynbricityspree will take place! 

Up next: the packing list & how I wore it!

Posted on June 3, 2015 .