A Whirlwind Weekend in Chicago

An opportunity arose and we had to jump on it: a long weekend with no plans. What could possibly be more fun than going on a little road trip than a road trip to Chicago?! We’ve been wanting to visit the city for a few years now, and this past weekend was our chance to do so! After having prepped and planned for our trip, we took off early Friday morning and headed to the city. From where we live, it only took about 6.5 hours, which was definitely doable in a half-day. Fortunately for us, the drive was a breeze. We didn’t have any heavy traffic until we reached Chicago. And by then, it was practically expected – rush hour on a Friday in the 3rd largest American city equals traffic jams. But it was ok because it meant that we had arrived!

We stayed at the beautiful Wyndham Grand Riverfront Chicago Hotel, on East Wacker Drive. It was the perfect location, centrally located to a lot of great sights and attractions. Upon checking in, we were informed that our room would be riverfront and on the 37th floor. Entering our room and seeing our view of the Chicago River was just the start of how great this trip was going to be! Check out our views below!:


After freaking out (in the best way) about our view and unpacking some things, we headed straight back down and went on a hunt for food. We had no idea of what was near us, so we ended up asking for some suggestions. The gentleman we spoke to suggested that we try The Billy Goat Tavern located under the city (by the train tracks) – it seemed like a super weird location, but when in Chicago…! Once we made it down the stairs and around the corner (exactly where he told us it would be) we entered and were greeted by the kitchen staff. We admitted that we hadn’t been to this venue before and they told us exactly what to get (a double cheeseburger, of course!). Once our order came out, toppings and condiments were available on a counter to the side. We loaded up and sat down to eat!


After eating, we headed back up to street level to start exploring! Our first attraction was the Chicago Architectural River Cruise with Shoreline Sightseeing on a double-decker boat right on the Chicago River. This was a fantastic tour and if ever you’re in Chicago, you should definitely check it out. We learned a lot about the history of the buildings along the riverfront, and were even shown where scenes of a number of famous movies were filmed! Pro tip: if its relatively warm in the city, that doesn’t mean that it’ll stay the same temperature on the boat. Although we had our jackets with us in the 12 degree (celsius) weather, it was a LOT colder on the water. Be sure to bring warm clothes!


After our cruise, we took a walk around the Magnificent Mile, then headed to dinner at The Purple Pig – a tapas style restaurant on Michigan Avenue. The food and wine was to die for! We were so full after our meal, and it was also getting late, so we called it a night and headed back to our hotel to be refreshed and ready to go for a full day ahead.

Saturday morning we started early – out the door by 7:45, eating breakfast at Corner Bakery Cafe by 8. After breakfast, we headed over to the stop to pick up our tickets from the Big Bus Tour, which is a hop-on, hop-off double-decker bus that takes you on a tour through the city. You’re free to get on or off to see any attraction at any point during the day. It was definitely a great way to see the city and get around.


Our first stop was the Willis Tower (or Sears Tower, as it was formerly known). This was such a cool experience. The Willis Tower is the tallest building in Chicago, standing at 442.1 metres with 108 stories. We ventured up to the observation deck to take in the view. While we were up there, we also had the chance to step inside of a glass cube (floor, walls AND ceiling) that protruded outside of the building. It was terrifying, but so awesome. Definitely a must-do if you ever visit Chicago!20170422_103056-0220170422_103253-0120170422_104630-01

After Willis Tower, we caught the tour bus and headed down to Millennium Park to see Cloud Gate, A.K.A “The Bean”. This was a neat experience. We weren’t expecting it to be such a large piece of art! Millennium Park was also a very beautiful place to see. It was filled with a lot of nature and boardwalks.IMG_20170427_101856_792IMG_20170427_084224_307IMG_20170427_102120_213IMG_20170427_102020_975

We wandered to the far side of Millennium Park and made a stop at the Art Institute of Chicago. This place was also massive. There were so many pieces of beautiful artwork to be seen, it was a lot to take in! Some of our favourite pieces were:

A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat,
Nighthawks by Edward Hopper, and
Paris Street; Rainy Day by Gustave Caillebotte,

…but of course everything was mesmerizing. We could have spent an entire day there! However, knowing that we only had one full day to see the rest of Chicago, we cut our time short. Back on the bus, and off to Navy Pier we went! At the Pier is where we tried deep dish pizza and a true Chicago hot dog. Both were fantastic, obviously. At the Navy Pier, we also took a ride on the ferris wheel, and took a tour of the lake!


By this point, the afternoon was nearing it’s end, and there was still one last stop that we wanted to see before our tour bus stopped running for the day: 360 Chicago (formally known as the John Hancock Observatory). It is the second tallest building in Chicago, if you include its antenna in the count. Because of its close proximity to Lake Michigan, 360 Chicago has gorgeous views of the city as well as Chicago’s beaches. While we were there, Alicia tried out the Tilt! Experience, where you enter a designated viewing platform, enclosed in glass, and are lowered down to hover 1000 feet above the city of Chicago!


After 360 Chicago, we caught the last bus of the tour back to our hotel. Feeling hungry, we went for dinner at the Mexican restaurant/ lounge bar La Mez. The food was fantastic and the staff were great! A lively atmosphere, and a wonderful time. After filling our bellies with tacos and nachos, we headed back to our room to rest up for our long drive back home the next morning.

Visiting Chicago in a weekend was definitely jam-packed and full of fun. If you’re looking for a little getaway and are considering a unique city in the United States that isn’t New York City, we definitely suggest that you check out Chicago. A lot of culture, great food, and beautiful views!

–The Calkins

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