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CHICAGO | Windy City in 5 days!

Welcome to Chicago! Home of the Chicago Cubs, Chicago style pizza, and some of the worlds tallest skyscrapers. John and I spent 5 days in this beautiful city and we can’t wait to share our adventure with you!

All the Food!

We pretty much spent our 5 days eating our way through the city… and we learned that Chicago has a taste of everything! Here are some of our favs.

  1. Hing Kee Restaurant in Chinatown – You have to stray from the beaten path and into the cultural hub of Chinatown, but it is worth every stop along the Red Line for the YUMMIEST soup dumplings we’ve had on this continent (We’ll let you know if that changes).

  2. Grand Lux Café – Out of the dozens of friends who gave us tips for Chicago, Grand Lux made it on everyone’s recommendation list for being a classic Magnificent Mile experience. With a menu ranging from beignets to burritos, this place is the Cheesecake Factory of Chicago.

  3. Giordano’s & Lou Malnati’s – A Chicago Pizza turf war that has been around for decades. We tried them both…and we decided we prefer pasta.

  4. Starbucks Roastery – Picture… Willie Wonka meets coffee.

  5. Portillo’s – John assured me that the Chicago style hot dog was great, but I couldn’t get over a 7 ingredient hot dog. Give it a try and let us know if you agree.

  6. Quartino – We found an amazing escape in the middle of the busy city. Enjoy a carafe of wine and more bread than you can eat at this small Italian bistro.

  7. Gayle V’s – In the mall? Want to try the best grilled cheese you’ve ever had? Do yourself a favor and go here.

  8. Untitled – Chicago’s Best Kept Secret. I can’t say enough about this place…step back in time and enjoy a night of amazing food, blue jazz entertainment, and the most comprehensive spirits menu you could ask for. Stay late for a burlesque show, and dessert! While you may need to save up for this dinner (and make your reservations a few weeks in advance), it’ll make your trip to Chicago unforgettable.

City Views from Every Angle

It’s no secret that Chicago is a big city. But John and I were blown away by how beautiful it was!

If you look closely, the buildings are brightly lit in New Year’s Eve colors. This sweeping view is from the Shedd Aquarium (which was my fav place ever #belugawhales)

This view is from the 103rd floor of the Willis Tower Skydeck… yes we are standing on a glass ledge overlooking all of Chicago… yikes!

Chicago is also known for it’s shows, museums, Wrigley Field, and so much more. We just skimmed the surface.

Stepping into 2020

John and I were lucky enough to celebrate the end of a decade in this beautiful city. We attended the Crystal Gardens New Year’s Eve Gala and it was… epic. From unlimited drinks, food and music to a firework show at the end of Navy Pier, we couldn’t have asked for more.

We hope this encourages you to take a city getaway to the Windy City. Pack warm and enjoy:)

Love overflowing,


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