I’ve always wanted to visit Chicago. It’s a major city somewhat near New England, yet very out of reach. As we planned this road trip we knew Chicago would be one of our first stops. Long story short, we're glad we stopped!
The night before our arrival to Chicago we embarked our road trip from NH and stayed the night in Pittsburgh PA. The next day we drove from Pittsburgh and arrived in Chicago just in time for dinner. After we checked in our Lake View Airbnb (and me almost losing my wallet), we walked to a nearby pizzeria to finally try some Chicago deep dish. We went to Lou Malnati’s and ordered their large signature pie with sausage, extra cheese, and a buttered crust. It was decadent, but I was nearly full after a slice and a half!
The next morning we woke up at 5am to catch some morning light in the city. Luckily our Airbnb was near a CTA station that took us straight downtown to Millennium Park. Our goal was to capture The Bean with no one around. When we arrived, there were a few people there, but no where near the large crowds the park usually gets during the day.
After The Bean, we just walked around the area a bit to take in the urban nature of Chicago. My favorite thing about Chicago was the exposed transit system. Nicknamed the ‘L’, short for elevated, the system consists of tracks and stations all above ground. They make for great shade in the mid-day, but the noise level gets pretty loud when the trains zoom by.
Some other highlights during the day was coffee at Big Shoulders Coffee, a tour of the Chicago Institute of Art, and a huge mid-day nap back at our Airbnb.
In time for sunset, we had plans to visit Skydeck Chicago at Willis Tower. The wait to get up was about an hour long so we decided to go to 360 Chicago instead at the Hancock Tower. Although we didn't get the 'glass box' views the Skydeck offers, we still got an amazing 360 degree vantage point for almost no wait and less cost!
After sunset we headed to Summer House Santa Monica for a wonderful (and a bit expensive) dinner in a great ambiance. We retired back to our Airbnb for the night to prepare us for the next day. The next day we dedicated solely to driving to Wall, South Dakota a 12 hour drive from Chicago.
I wish I had more time to really explore the depths of Chicago, but I'm glad I scraped the surface.