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Weekend Recap: 48 Hours in Chicago

This past weekend we took a quick trip up to Chicago!  Good friends of ours, that we had met while we lived there, were having a going away party.  They are originally from Germany and are moving back home after living in the US for eight years.  We love taking weekend trips that allow us to experience another city without needing to use our precious vacation time.  Plus, Chicago is one of our favorite cities, therefore we come as often as possible!


“She is always a novelty; for she is never the Chicago
you saw when you passed through the last time.”

~Mark Twain

We took the early morning, 6:45am flight on Friday morning to fly up.  For quick weekend trips, we prefer the early flights for two reasons; they are typically cheaper and it gives us a full day to explore/visit at our destination.  Upon arrival, we headed straight to Tortas Frontera in Terminal B of O’Hare airport.  It is one of chef Rick Bayless restaurants and the best airport restaurant food we ever had.  We had a quick snack of Bacon & Queso, as well as, Smoked Pork molletes.  We highly recommend anything on their menu!


After our quick snack and checking into The Hard Rock Hotel Chicago, it was time for lunch at Sienna Tavern.  Along the way, we walked up Wacker Avenue which offers some beautiful views of the river and skyscrapers.


Friday was lovely weather so we enjoyed our lunch outside on the patio.  I had a lobster roll and Brian chose the Mortadella Melt.

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Following lunch, we were in need of dessert and headed to Firecakes for doughnut ice cream sandwiches…..yes, I just said doughnut ice cream sandwiches!!  Since we don’t like chocolate, we skipped the hot fudge but I suspect most people will add it.  If you are not in the mood for ice cream, they have several specialty doughnuts as well.



Next stop was one of our favorite outside spaces in the city, the Terrace at The Trump Hotel.  It’s an outdoor terrace located on the 16th floor of the building.  In our opinion, it offers one of the most stunning views of the city!


The Wrigley building is one of our favorites among the skyline and at The Terrace, you get a very intimate look with the beautiful clock tower.  It’s a great place for a cocktail but we will warn you, they are a bit pricey but totally worth it in our opinion.




After our cocktails, we walked around the ground level of the building.  There are some great views down there that offer a different vantage point of the city.




That evening, we headed to a kid friendly Japanese restaurant with our friends, Cocoro.  It is traditional Japanese food so we decided to try the Shabu, which we had never eaten before.  Unfortunately, we were underwhelmed and did not enjoy boiling our own food.  In addition, there was no flavor, and it was very bland.  Assuming this is a traditional dish, we won’t be trying this anytime soon, or ever again.

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The next day we woke up to a 30 degree temperature drop and fog!  Got to love spring time in Chicago!   When traveling, we always pack clothes that can be layered as well as an umbrella.  You can’t control the weather so it’s best to be prepared to make the most of your time.  We decided to head over to Millennium Park to get the obligatory picture in front of the Cloud Gate sculpture, better know as “The Bean”.  No matter how many times we go to the bean, we love to see the changing reflections based on the weather.



The Park around the bean is a great spot in the spring as the tulips add a touch of color to your photos.  In the summer, there is an outdoor amphitheater that offers some great performances.



Since we slept in a bit to recover from our 3:45am wake-up call on Friday morning, we skipped breakfast and headed to an early lunch at 11:00am.  In honor of the Bulls play-off game win, we decided to support The Bulls legend, Michael Jordan, by going to his steakhouse.  The main dining room isn’t open for lunch but they have food service in the bar area which includes several of their specialty menu items.



We started with the Nueske’s Bacon Appetizer, WOW!  It was incredible!!  It came with 4 thick slices of bacon that were grilled just perfectly and had the right amount of maple glaze sweetness.  Oh….my…..goodness…….If you go here, do not even hesitate and order this as you take your seats, we promise you won’t regret it!


For our main course, we decided to split their 16oz signature MJ’s Delmonico which is dry-aged for 45 days.  It was cooked to the perfect medium rare that we ordered and every bite was more delicious than the last.  We can fully appreciate that it was named one of Chicago’s 10 Best Steakhouses!


Next stop was to Bin 36 to enjoy some afternoon wine flights with our friends.  We created the perfect cheese & meat pairings to enjoy along with it.

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After our wine stop, we spent the remainder of the day/night with our good friends reminiscing about great times we’ve had over the years.  It was awesome to see all of our “Chicago family”.

Overall we had a lovely 48 hours in Chicago!  It was definitely filled with great food & wine!   As always, Chicago provides a stunning backdrop with excellent restaurants to chose from.  Until next time Chicago…….


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  1. Love the pics, guys! You captured your trip very well! Until we meet again!!

  2. […] of our favorite US cities – Chicago.  Right before we moved away from Chicago, we hired Genevieve from The Way We Click to capture us […]

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