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Welcome to Chicago

June 6, 2013

Once upon a time at my birthday dinner, my friend and her mom mentioned that they were taking a trip to Chicago to see The Rolling Stones in concert.  “What?!?” I believe I replied, “Without me and my mom?”  Less than a minute later I had my mom on speakerphone at the dinner table, and less than an hour later we had concert tickets and flights booked.

Fast forward about a month and a half, and I’ve just returned from a fabulous weekend with my momma and a knock-out concert.

We arrived in Chicago on Saturday afternoon and checked into the Raffaello, a boutique hotel right off Michigan Avenue in Streeterville that would act as our home base for the weekend. 

Raffaello Hotel

We (and by we, I mean my mom – thanks Mom!) had an insanely hard time finding a hotel room for the weekend as the thousands of rooms downtown seemed to be booked even in early April when we made our plans.  The Raffaello was a lot pricier than it should have been (again, thanks Mom!) but spectacularly located.  We were just two blocks off the Magnificent Mile, right down from Watertower Place and the Hancock Building.  Lake Michigan and the Lakeshore Path were two blocks to the East.

Our friends wouldn’t arrive until Monday morning for a whirlwind 30-hour stay, so we were on our own for a few days of mother-daughter fun.  After traveling since early that morning we were famished so we walked down the block to The Grill, a nearby restaurant recommended by the woman working the front desk at our hotel.  It had a clubby atmosphere and a pretty cool bar area where we scarfed down yummy sandwiches.  As soon as we finished eating, the gray skies opened up and it started to rain.

Michigan Avenue

Without a better plan, we dashed into the open arms of the nearby storefronts and shopped for a few hours while waiting for a break in the clouds.  Once the rain eased a bit we walked down Michigan Avenue, and Chicago was dazzling even in the drizzle.

Michigan Ave Carriage

Mag Mile

Before too long, we were in the mood to get out of the cold, damp weather and into a glass of wine.  I jumped on Yelp, my go-to for restaurant recommendations while traveling, and looked for a nearby wine bar.  Hundreds of four-star reviews pointed us toward the Purple Pig, but when we walked in it was standing room only, so we walked across the street to Eno.  With plenty of open seating and a menu of wine, cheese and chocolate flights, we were pretty much in heaven.

The chocolate cases welcomed us to Eno with style.

The chocolate cases welcomed us to Eno with style.

I tucked into a flight of “revolutionary” whites that were new varietals for their particular regions.  I wasn’t wowed by the Pinot Grigio (but then, I’m usually not), but I really liked the Walla Walla Chardonnay and the Columbia Valley Riesling I tried.  My mom sipped a Pinot Noir rose that was light and refreshing.

Eno Chicago Flight

Still full from our late lunch, neither of us was particularly hungry, but we couldn’t resist the idea of a chocolate flight.

Eno Chocolate Flight

I’m pretty sure this was the “Caramel Dreams” flight, and the two caramels and one toffee were delicious.  But at $11 for three small pieces of chocolate, I’ve got to hand it to Eno – they’ve definitely got a business model figured out with the chocolate flights, if you know what I mean!

As we were sitting there the rain picked up and we knew it’d be impossible to catch a cab, so we just had to order another round.  We both selected a glass of Illahe Viognier from the Willamette Valley, and both absolutely fell in love with it.  It was floral, full-bodied and just perfect.  I’ll be on the lookout for this wine in the future and just had to mention it in case there are any other Viognier lovers out there.

Rainy Chicago

Once the wine had let up a bit, we finally made our departure from Eno and ventured back toward the Raffaello to meet a good friend of mine from college for a late, light dinner of thin-crust pizza and sangria at Bar Toma.  It was a great catch-up at a fun spot and we chatted until my mom and I started to get sleepy from our long day of travel and wine drinking.  With that, we headed back to the hotel to rest up for our first full day in Chicago.  More city adventures to come tomorrow!

4 Comments leave one →
  1. June 6, 2013 2:32 pm

    You are making me miss my home town! I worked on Michigan Avenue for years just on the other side of the river! I hope you hit Lou Malnati’s, sometimes I miss that pizza more then my family!

    • June 6, 2013 3:32 pm

      I didn’t realize you were a Chicagoan! I LOVED my time in your hometown and am happy to report that I had a delicious lunch at Lou Malnati’s and totally get it – family can come visit… pizza, not so much 🙂


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