CHICAGO, IL
Curious what you can expect from a long weekend in Chicago? Well, rest up because you’ll be ON THE MOVE with so much to fit in during a short time! I would definitely recommend a longer stay, but you can learn from MY mistakes, right?
Be sure to scroll thru this page to take advantage of some tips and tricks I learned along the way!
Things to do…
Don’t miss Buddy Guy’s Legends…
Opening at 5pm, stop in for a cocktail or a quick bite and catch some great local blues. There may be a cover (it was $15 the night we were there), but don’t let that scare you! This night Mzz Reese and her Pieces was on the bill, but Mr. Buddy Guy himself gave a surprise appearance and took the stage for about 1/2 hour! They have a wee merch shop and Buddy hung out to sign autographs and take pics after the show!
The Art Institute of Chicago
Skydeck @ Willis Tower
Chinatown
Downtown Skyline
Grant Park
PRO TIP!
River Tours run rain or shine! If the weather is good, be sure to grab a seat on the upper deck so you can see both sides and take in the sights as the guide describes them in real time. If it’s wet and rainy (like it was for us), the lower deck offers interior shelter and covered deck seating -but be sure to get on the right-hand side of the boat, starboard side, if you will. The majority of the sights are on that side!
Millenium Park - Cloud Gate
90 Min Architecture River Cruise
Ghosts & Gangsters Tour
Lake Michigan
Navy Pier
The “L”
Just because Chicago is an extremely walkable city doesn’t mean you MUST walk everywhere. Take advantage of the efficient and reliable L-train. The Citymapper app and Google Maps both list train options when you search directions. You can get a 3 day unlimited pass for use on the train or bus for $15.00.
Chicago Eats!
Chicago Secret - Skydeck Saturday Lunch Package!
After the 103-story views of the city, sit down at Kindling and enjoy lunch from a prix fixe menu. Reserve ahead and get admission to the Skydeck, a soft drink, and an entree for $60 each. Be sure to tell them if you’re celebrating anything special ~ we were greeted with champagne to celebrate our 25th wedding anniversary! You never knew you wanted champagne with your Italian Beef! And if you’re lucky, the bartender will be practicing his Espresso Martinis and use you as a test subject! Honestly, it was perfect, and he didn’t need the practice!
Don’t forget Chinatown! There was so much to choose from but on this cold and rainy day, we opted for a bowl of hand-pulled noodles in a rich and complex broth to warm us up.
Now I’ve never met a donut I didn’t like, but Stan’s donuts are officially THE BEST! I don’t think I’ve ever lost a battle to a donut before, but this Biscoff Pocket got the best of me. No regrets, though… the number of steps walked in those few days justified it, if only in my head.
No trip to Chi-town is complete without sampling the iconic Chicago Dog! The signature neon green relish, pickle, celery salt, tomato, onions, and sport peppers are a perfectly balanced delight!
For the pizza fan, deep dish done right can be found at Lou Malnati’s. For the complete Chicago experience, I recommend the Sausage and Cheese!
Eleven City Diner is full of surprises, but go early because - SURPRISE - they’re only open until 3pm! From sweet and savory breakfast options (we tried the Challah French Toast and the Pastrami Hash Bowl) to Deli lunches, they have it all… even a candy counter and old-fashioned soda fountain.
The Arts~
The Blackstone
In the late 1800s, Timothy Blackstone, president of Union Stock Yards and the Chicago & Alton Railroad, builds his mansion on the intersection of South Michigan Avenue and Hubbard Court (now Balbo Street). It was later sold in 1900 upon his death. In 1908, the hotel plans are drafted and the construction is completed in 1910.
An Associated Press reporter dubs Suite 915 the “smoke filled room” when Republican leaders and party power brokers meet secretly in this room and nominate Warren G. Harding as their party’s candidate for president.
Al Capone held meetings while getting a haircut in the windowless barbershop.
Major Motion Picture, The Color of Money, starring Paul Newman was filmed in the Crystal Ballroom.
Also visited by Marily Monroe, The Duke and Duchess of Windsor, JFK, Harry Truman, and Dwight Eisenhower.
Charles “Lucky” Luciano hosts the first-ever Crime Convention in the Crystal Ballroom of the Blackstone. The event was hosted with the intent of establishing a board of directors for his “National Crime Syndicate”.
