09-12 May 2024 - Chicago!

I had 3 fabulous days exploring The Windy City!

On Thursday, I left Minneapolis and headed southeast towards Chicago. About 4 hours into my journey, I stopped for a late lunch with friends Mike and Kathy near Madison, Wisconsin. Mike and I worked together a long, long, LONG time ago and it was so nice to finally see where they live after all these years.

I continued on to O’Hare airport where I picked up Randy who is coming out to join me for a long weekend. We went into downtown Chicago and met up with our friend Terry and his happy hour gang.

On Friday morning, we headed out to explore Chicago. Randy had a list of local foods he had to try and we literally spent the entire weekend eating our way through the city. First up Friday morning was a place called Levion‘s which has the world‘s most amazing cookies – slightly crispy on the outside edge but soft and chewy gooey on the inside – a giant chocolate chip cookie and a cappuccino made for a perfect breakfast for me. I grabbed it to go because Randy wanted to have an Italian Beef Sandwich from Portillos. Their famous sandwich is seasoned roast beef served on French bread with sweet peppers which is then dipped in an au jus sauce. Rumor has it that the best way to eat it is to have a wide stance and sit far back from the table so that all the juices don’t get all over you. It’s messy but boy is it delicious!

From there we caught on a hop-on hop-off bus tour so that we could see some sites and familiarize ourselves with the city. We decided to get off at the Federal Reserve Museum, as it’s only open M-F. The museum had several cool facts about the bills they print and shred but 3 displays really caught our eyes. Each was worth $1 million and the size differences were quite astonishing: The first was a 4‘ x 4‘ cube of $1 bills that weighed over 2000 pounds. If you get your million dollars in $20 bills it all fits into a neat dome about 2 feet in diameter. And lastly, if you have $100 bills you can fit $1 million into a small suitcase . Pretty cool!!!! and the Chicago fed shreds up to $26 million per day. They give a free bag of shredded cash to each visitor and I look forward to showering myself with shredded money some day. 😂

We continued on to Millennium Park where we had to snack on a true Chicago Hot Dog; you order it “Dragged through the garden” which means it is served with relish, a spear pickle, tomato, celery salt and onions on a poppyseed bun. And yellow mustard …. But I REALLY hate mustard ( and ketchup is forbidden!) so I ordered mine without mustard. Shame on me!

We saw the famous Bean sculpture in the park (sadly currently a construction site as they work on the patio area around the Bean); the artist originally named it Cloud Gate as it was to reflect the sky and clouds against the city skyline backdrop but it looks like a bean and the nickname has stuck, much to the artists dismay. Checked out some other art installations and sites throughout the park, and then we met up with friend Sammy at a rooftop bar – views were great and so were the specialty cocktails! We then went to Prime and Provisions, an amazing Chicago steakhouse. Soooooo delicious!l We ended of the evening by going to Second City and enjoying their improv comedy show. Second City has been a starting point for many comedians, award-winning actors, directors, and others including Alan Alda, Bill Murray, Gilda Radner, John Candy, John Belushi, Dan Aykroyd, Chris Farley, Colin mockery, Ryan styles, Mike Myers, Steve Carell, Tina Faye, Amy Poehler, Stephen Colbert and many others. What a full day!!!!

On Saturday, we headed out to the Navy Pier. Spent some time walking around and checking out all the restaurants and stores in the former navy hangars, then decided to take a ride on top of the giant ferris wheel. Each car is a gondola that can seat up to 8 people but we were lucky enough to get one all to ourselves. It was a gorgeous day and the views of the city up top were breathtaking.

Then was time for another famous Chicago food snack: deep dish pizza at Giordano’s. Oh my is that pizza thick and delicious - its so thick it takes 45-60 minutes to bake!

A little more walking around and then we met back up with our friends at Billy Goat Tavern - for all your old timers it’s the place that the Saturday Night Live skit with the famous lines “cheeseborger cheeseborger cheeseborger” and “ NoPepsi, Coke!” and “No fries, chips!” is based on. It’s a total dive with a fun throwback atmosphere and the owner/cook still plays the part and grills the burgers and barks out at the customers.

Afterwards we joined Terry and his extended family and took a 2- hour architectural tour via boat through Chicago’s river systems. I never would’ve considered taking an architecture tour and it turned out to be so interesting! Our docent was really informative and Chicago has a variety of really interesting architecture. Plus it’s always fun to be on a boat!

Post tour, we walked the Miracle Mile which is a section of Michigan Avenue that boasts lots of famous and expensive shops. One feature is the world’s largest Starbucks. This location is not only a 5-story Roastery but also has a bar on the 4th level. They feature lots of coffee drinks but also have a full bar that can serve whatever you’d like. Who knew there were Starbucks that served booze?!?! We continued to dine our way through Chicago atvtye Purpke Pig - the tuna tartar appetizer in a round baked octopus-ink cracker was as visually appealing as it was delicious.

Sunday was Mother’s Day – happy belated Mother’s Day to all the moms reading this. We headed out to do some more exploring and I couldn’t resist taking a picture of the candle that was in a craft fair that we browsed through - a very funny Mother’s Day gift!

We saw a Museum of Ice Cream and thought it would be fun to go in and try some ice cream and learn about its history. We were EXTREMELY disappointed to find out that it was more like a children’s museum that was geared towards kids birthday parties and some Instagram picture opportunities and that it was neither informative nor was the ice cream very good. They had the most bizarre flavor of ice cream there too: hotdog! Yes, it’s in honor of the Chicago Dog and it is served on a horizontal “cone” which looks a “bun” complete with poppy seeds. It has the spices and flavoribgs of a hotdog and the smooth texture of ice cream – it did not compute well in my brain. Apparently there are Museums of Ice Cream in a few different big cities – if you ever encounter one be sure to skip it!

We decided to walk off the ice cream calories by heading out towards Lake Michigan and walking along the bike and pedestrian pathway along the lake. It was an absolutely gorgeous day with temperatures reaching 80°. Once we had walked off the ice cream we decided that we needed one final deep dish pizza before leaving Chicago. We enjoyed playing cards outside while waiting for our pizza to cook and then sadly it was time to bring Randy back to the airport and end our fun foodie tour of Chicago.

i need to spend the next several days working off all those Chicago calories!