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Chicago exceeded all expectations.  The weather was that perfect mid to high 60s that made us want to be outside as much as possible.  This was my first time ever to Chicago, but I already know it won’t be my last.  One weekend seemed like far too little time to explore all of the architecture and rich social and cultural history the city has to offer.  We also walked everywhere we went, and absolutely loved it.

What must you do?  A late night dinner at Girl & the Goat and an early morning architecture river tour were easily our favorites.  Girl & the Goat requires reservations 2-3 months in advance (no joke!).  However, they also allow walk-ins (our wait was about 2 hours).  We put our name in and then walked around the west loop neighborhood, which is full of cute pubs, restaurants and shops.  We stopped into Lonewolf Tavern to have a drink while waiting.  The place was cozy and they offer a wide variety of craft beers from local breweries.

And finally, Girl & the Goat.  David and I both agree that it was arguably the best meal we have ever had.  Our two main courses were the crisp braised pork shank and the goat empanadas.  The pork shank, which fell right off the bone, was paired with a buttermilk dressing, naan, and a kimchi wing sauce.  The goat empanadas were served on top of an avocado smash, topped with strawberry tapenade and queso fresco.  I did not expect to walk away ranting and raving about the goat, but my goodness! It’s safe to say we enjoyed e v e r y  l a s t  b i t e.

I could blab on endlessly about the details of each place we visited, but instead I’ll just share a few highlights.

> Gino’s East – The place with the best deep dish pizza in Chicago is a huge dilemma, but I vote Gino’s.  The cornbread crust is to-die-for.  Lou Malnati’s for the win if you love thin crust.
> Lakefront trail – The water is an unbelievable turquoise color.  We spent most of our last day lounging on North Avenue Beach.
> Cindy’s – Rooftop restaurant at the top of the Chicago Athletic Association Hotel.  Unique cocktails and an incredible panoramic view overlooking the city and Lake Michigan.
> City Winery – Along the River.  If you love mozzarella, get the burrata.
> Art Institute of Chicago
> Acanto – The best grilled cheese sandwich I think I’ve ever had.  Also, the bellini flight.  My favorite was the Perugia (Prosecco, walnut orgeat, amarena cherry and lemon).

> Signature Lounge – A beautiful view of the city from the 96th floor of the John Hancock building, but you have to get there early enough to get a table with a good view.
> Skyledge – At 1,353 feet in the air, the glass boxes extend out 4.3 feet from the 103rd floor of the Willis Tower.
> Le Pain Quotidien – The most adorable bakery.  They also serve lunch and dinner, which I’m sure is every bit as good as their pain au chocolat.

Chicago - Architecture River Tour

Chicago skyline

Until next time, Chicago!


  • I live here and you really did Chicago right! I’m glad you had a good time 🙂

  • Sarah Singleton

    Great blog! We’re headed to Chicago this weekend and reading your places to go was really helpful and made us all the more excited! Your top two must activities were already on our list!

    • Ah! You will absolutely love it. Hopefully you have some pretty weather. There’s so many fun things to do! Hope you are doing well, Sarah. Have a great trip!

  • Cameron

    Looks like an amazing trip!! <3