Lifestyle Travel

SWEET SUMMER ROAD TRIP SERIES​: CHICAGO TRAVEL GUIDE

There’s something special about big city lights that give me that boost of inspiration that I need to make my sweet dreams happen!  As the summer comes to a close, we made the 8-hour road trip up to Chicago just before the gusty winter winds freeze the beautiful city over.  If you’ve never been to the Windy City in the summer, you’re missing out.  The bustling streets are full of locals and tourists enjoying the weather, shopping, and eateries all along the coast of Lake Michigan.  For 48-hours we explored and enjoyed every aspect of this city! Without further ado, here are my recommendations for your trip to Chicago!

Transportation: 

If you live within the 8-hour radius of Chicago, I recommend driving! Especially if you’re taking I-65 from the south.  There is an amazing stop on the drive called the Meadow Lake Wind Farm that is the most amusing rest stop ever!  It’s miles and miles of corn fields that have windmills in the middle of them.  It is a sight to see and wonder about.   Special thanks to Enterprise for carrying us through the scenic view in our Hyundai Tucson.  We felt safe and comfortable the entire way!

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Accommodations:

Our stay at the Kimpton Hotel Allegro was more than pleasing.  In the heart of the Theatre District lies this beautiful oasis of luxurious decor.  The “Great Gatsby” effect makes you feel like an extra on the actual movie.  You’re greeted with the most hospitable bellman as soon as you arrive.  Check-in occurs in what resembles a ballroom.  You literally feel like you’ve been invited to a party as an exclusive guest.  The concierge staff greets you with glasses of Prosecco to give you the element of relaxation that you’ve been yearning for! When we went up to our King Suite, we were instantly in awe of the cozy, spacious room.  An unexpected text popped up on my phone from the concierge welcoming us with the language, “I’m only one text away.”  In this digital age, it was a pleasure to be able to request whatever we needed whether we were at the hotel or not!   The convenience of this was perfect for our weekend debrief of a busy work week.

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Eateries: 

  1. ZBAR

Date night is an important pastime of ours so we made our way to Zbar for cocktails and conversation!  The view was perfect and boasted all the city lights I needed to revive my energy from the drive.  We enjoyed the Butcher Clock which is three kinds of Artisan cheese chosen by the chef and local cured meats.  After our busy workweeks, the chill atmosphere allowed us to be in the moment and really enjoy each others company!

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     2. GIORDANOS

One of our favorite pizza places in Chicago is Giordano’s!  WARNING: All you need is one slice of their thin crust pizza before you’re in need of a nap!  This food is sooooooo good, but so filling.  If you’re looking for a Chicago style pizza, this is your place!

     3. 312 CHICAGO 

By far our favorite meal on the trip was brunch at this fabulous restaurant in Hotel Allegro!  Most brunch places you go to will serve you an average meal in an average environment.  This was a decadent meal in an exquisite environment.  It’s an experience!  The entire wait staff is attentive to your any and every need.  They know their menu and are willing to offer up the best suggestions to fit your preferences.  The best part is their “Build Your Own Mimosa” option!  You take your pick between Orange Juice, Grapefruit Juice and two select seasonal juices that you can mix with a refreshing glass of Champagne.

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Fritto Misto: Fried Calamari, Baby Smelt, Shrimp, Salmon, Lemon, Frisée, Limoncello Aioli
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Seasonal Brioche French Toast: Custard, Fresh Berries, Banana, Sweet Whipped Cinnamon Cream Cheese

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Short Rib Hash: Potatoes, Scallions and Roasted Red Peppers, Two Eggs Any Style, Hollandaise Sauce

     4. Velvet Taco

This place has tacos like you’ve never imagined.  Just imagine a buffalo chicken sandwich on a taco!  Better yet, imagine a hamburger on a taco!  That’s what you get here.  After a long day spent at a rooftop pool, this was the perfect place for us to wind down at midnight!  The atmosphere is fun and free!

Lastly, heading to a rooftop is a must when you visit any city!  You need to get the sky vantage point to see what all you could potentially experience.  We made a stop by London House to check out their rooftop.  From this sweeping view, we were able to enjoy and meet new friends while staring out at the beautiful city of Chicago!

Until next time, these are my recommendations for a good time in the Windy City!

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