Our first trip to Chicago was a little over six years ago. Since that time we’ve been back almost once per year. I took the boys by myself five years ago. It’s still hard to believe that I pulled that one off. The next three Decembers Mandy and I took quick trips, coming to realize that if you can get over the cold, it was a great time to travel due to affordable hotel rates and the Christkindlmarket. And then this summer the four of us spent a couple of days there before going to Switzerland.
Several months ago Mandy heard that the musical version of The Notebook was premiering in Chicago this fall. She is a big fan of the book, movie, and of Ingrid Michaelson, who wrote the music and lyrics. So we booked tickets, flights and a hotel for one night.
Before getting into the specifics of this trip, let me tell you some reasons we have made such a habit of going to Chicago. First, it’s a quick nonstop flight from Memphis. Second, the food is great. Third, Southwest’s flight schedule enables us to get there in the morning and leave the next night, meaning we get most of two days there yet only stay one night.
This past Friday morning we got the boys off to school, finished packing, and drove to the airport. We opted for the $6/day economy parking over paying for two Uber pickups. My roundtrip flight set me back 16,000 Southwest points. Mandy’s flight was free since we have the Companion Pass this year and next.
We landed in Chicago around 1pm and then took the Orange Line train downtown. You can get a public transportation day pass for $5. This includes the train from the airport, plus trains and buses downtown. We walked a couple of blocks to Shake Shack (always a winner), then walked a couple more blocks to the Hyatt Centric. One night there cost us 15,000 Hyatt points, which I transferred from Chase. Note: if you’d like to know more of my travel hacking strategy, check out this page.
After resting for a bit we walked four blocks to have dinner at Quartino, our favorite restaurant in Chicago. As is my custom, I ate a bit too much, but it was ok, because we needed to walk a few blocks in order to catch a bus to Navy Pier, which is where the Chicago Shakespeare Theater is located. The Notebook was fantastic. The venue, music and performances were top notch, and I’m sure it is going to do great on Broadway.
On Saturday morning we chilled out at the hotel for a few hours. At 11:00 we checked out, left our luggage at the hotel, and walked a few blocks to RL Restaurant, another of our favorite restaurants. It’s all about the ambiance in this place. You’ll have to see it for yourself, but check out the link for a few photos.
From there we had a few hours to shop on Magnificent Mile, but since neither of us were that into shopping at the moment, we hung out at the Starbucks Reserve Roastery, where we enjoyed good coffee, a pastry, and some time to catch up on reading.
Our final hours in Chicago were spent on an Architectural walking tour that I booked through Airbnb Experiences. Mandy and I highly recommend this. We learned so much about Chicago, explored places we would have never discovered on our own, and saw some amazing architecture and art. Our favorite stops would have to be the Chicago Cultural Center and the Chicago Athletic Association, which is now a Hilton hotel. Check out this video about the Chicago Cultural Center.
Mandy walked a couple of blocks to the train station, and I walked back to the hotel to get our luggage, then took a bus to the train station. From there we took the train back to the airport, took the short flight to Memphis, and were back home by 11pm. We were pretty tired, but it was a great trip!
