Sippin Gypsy Quick Tips for Playin': Chicago

Cheers Sippin Gypsy Team Vodka! This post comes to you while enjoying my Sippin Gypsy Spicy Vodka Sip while reminiscing of my adventure in Chicago.  You can check out other tips for Chicago HERE!

Chicago is an amazing city.  I've been to most of the "large cities' here in America and Chicago is simply wonderful.  I really appreciate the balance of industry and community.  Set on beautiful Lake Michigan, and cradling Grant Park, Chicago offers everything from impressive high rises to peaceful outdoor retreats. My time in Chicago was not nearly long enough to begin to uncover all the true gems this city offers for entertainment and adventure.  But if this is your first time to Chicago, this list will certainly get you started and give you the slightest taste of this incredible city.  

1. The Sky Deck at The Willis Tower
I highly recommend taking in the majesty of the Chicago skyline from 110 floors up.  This is a great way to start your first day in Chicago to understand how massive her sprawl really is.  Plan on going before sunset to give yourself time to get to the top then watch the magic unfold as the sun sets and the city lights dust across the city as far as your eye can see.  Its truly a humbling and inspiring experience.  I would highly recommend purchasing the City PASS for the Sky Deck as well as a few of the other places they include that I suggest on this post.

2.Grant Park and Millenium Park
I love green space.  Both Millenium Park and Grant park is a peaceful oasis cradled from the bustle of the Chicago streets.  The iconic Cloud Gate sits just steps into Millenium Park.  There are playground areas and isolated reading benches and a stunning landmark,Buckingham Fountain.  As in any city park, there are events and festivals held regularly.  Refer to local publications and the parks websites to see what is happening during your visit.  Grab a sandwich and snacks and give yourself an afternoon enjoying the park before heading out for a night on the town.  

3.  Tours
You know me, I'm a sucker for a good ghost tour, but I always try to get in a history or architecture tour in any city I visit.  Chicago has SO MANY TOURS!   Top on my list is the Prohibition Tour where you get to visit Chicago's speakeasies and learn more about the dark history of alcohol during prohibition.  This tour does not include the cost of cocktails as you travel, so bring a little extra to sip as you learn. TheChicago First Lady Tour is a great way to learn about the iconic architecture of Chicago from the comfort of a boat!  And good news, you can Sip and Sail on the First Lady Tour, they have a full bar that is available for a separate price.  I also tried to check out the Free Chicago Walking Tours.  Because this is run locally as the tour guide is available, the calendar is limited to getting the tour you may want when it fits within your schedule.  But this is run by passionate Chicago locals who are excited to take you on a journey of their city.  Give it a try if it works with you agenda!

4. Tour a Museum
​​Remember that City PASS I recommended you get? This is where it really comes in handy.  Chicago is home to many amazing Museums and Exhibits that would certainly rival the Smithsonian in Washington DC.  The Art Institute of Chicago, The Field Museum, Shedd Aquarium or Adler Planetarium are all great ways to spend an afternoon and they are all included as options with your City PASS.  If you stay in Chicago allows, pick one Museum each day, spend a few hours enjoying the exhibits before continuing to other great activities.

5. Stroll through the charming historic Gold Coast neighborhood
This neighborhood was one of the few spared in the fire of 1871, so many of the stunning buildings are original.  The neighborhood is growing with eclectic spots for food and drinks and some of the most coveted shops in the country.  There are local tours offered for this neighborhood too, walk in the footsteps of some of richest men in Chicago that initiated the high rise and skyscraper revolution to put Chicago on the map for some of the highest and architecturally unique structures in America and the world.

6. Enjoy the Chicago skyline from a rooftop bar or restaurant
Chicago has several rooftop bars and restaurants throughout the city that offer breathtaking views of the skyline and shoreline.  Depending on where you stay, or what activities you have planned, save time to sit and sip and savor the view! Check out my Sippin Gypsy Quick Tips for Sippin': Chicago for specific spots with great cocktails and cuisine in the city.

7. Live Music
Several bars and hotel lounges will offer live music on most evenings.  Like New Orleans you can almost follow your ears to great music.  One of my favorite spots that I ended up going back to two more times was Andy's Jazz Club.  The musicians they brought in were passionate performers and the ambiance was lively and energetic.  I also enjoyed the Tortoise Club for dinner and live music.  It was fun to get dressed up for the evening and step back into this swanky spot with a richly appointed decor of dark woods and elegant details.  The drinks here were some of the best I had in Chicago and the food was truly favor packed and delicious.