As you may have learned, last month I managed to sneak a road trip over to Chicago with my girlfriend.  It was a first time for us to visit this city.  During this excursion, my girlfriend had scheduled us in for three walking tours for the two days that we were in town.

On the first day we had a food tour, courtesy of chicagofoodplanet.com.  During this taste of the Gold Coast and Old Town neighborhoods, my girlfriend and I sampled a slice of Chicago’s legendary deep dish pizza, tried some sushi and warm sake from Chicago’s oldest Japanese restaurant.  We also chomped on some really tasty treats at a chocolate shop, devoured some delicious killer pierogi and delighted ourselves with some tasty macrons.  While walking in between the restaurants and stores, we also got to learn some of the history about several buildings in the two neighbourhoods we were in.  We were entertained and educated about tea, olive oil, chocolate and spices while being invited to browse and discover different aromas and flavours.  Our tour guide was simply awesome!  Highly recommended.

After the tour, we took some time to walk around and take in some scenery as I still had time left in my parking spot.  Weather?  We had all sorts, from sunny with clear skies to fog as thick as pea soup!

After the walk, we got to try out a restaurant called The Girl & The Goat.  The restaurant had some great dishes.  We would have tried more but sadly I’m allergic to seafood.  Perhaps next time. Garfield made his appearance here!

On our second day, my girlfriend and I parked our car at Navy Pier and from there we took a hop-on, hop-off bus tour to get to our second walking tour that started at the Sears Tower.  Wait…Sears?  Yes – locals still call it the Sears Tower, although the building is now called The Willis Tower, just like most of us here in Toronto (coincidentally, one of Chicago’s international sister cities) will still call the Rogers Centre, “The Dome” or more formally, The Skydome. We feel your pain, Chicago.

Back to the second tour.  This was an architectural walking tour of “The Loop”, also known as Chicago’s downtown core.  We found it here.  Our tour guide was very well informed and although he seemed biased to particular architectural styles, we were taught and shown many details we could never have learned unless we spent the time to dig about in books.  We got a chance to learn about the history of the skyscraper, the loop, different styles (or schools) of architecture that started in Chicago and how Chicago maintained, what continues to be in my opinion, one of the best skylines I have ever seen.  If you like architectural design and history, this is a great tour to try out.

During the time spent between the architecture tour and our final tour, my girlfriend and I had lunch and walked back to the Sears Tower.  You may have spotted Garfield in one of my earlier posts.  It was a spectacular view, and although people will say to go to the John Hancock instead, I don’t regret spending 2 hours waiting to finally get upstairs to take a look.

Two hours in the Sears later…we are running late to catch the hop-on, hop off bus that would take us to our final walking tour – a twilight river walk and architectural tour!  We still managed to learn about “The mistake by the lake” and other trivia that got weaved into the fabric of the city.

So…we finally made it to our final meeting spot, and my girlfriend and I thought we were late.  We were about 5 minutes late in fact.  We frantically messaged the tour company to find out where our tour may have disappeared.  After 15 minutes of searching the streets and texting, we gave up.  More about this later…

Anyways, we ended up angrily walking from the Chicago Theatre all the way back to Navy Pier – not the best thing to do when it was such an awesome night.  I mean, the tour was free, but still.  We made up for this problem by wandering the city by car and looking for a place to eat.  We weren’t brave enough to head out of the car and wander into certain neighborhoods, but soon we found ourselves back in the Gold Coast, parked in front of Lou Malnati’s, and eating on the sidewalk patio at Carmine’s.

For a Saturday night, the scene was laid back, but hopping.  I had forgotten my phone and camera was packed in the back, so no photos to show.  As my girlfriend and I enjoyed the food, made up to ourselves for being upset with each other earlier and just simply being together, we watched tour buses driving around packed with people partying, and the other restaurants were bustling. Lots of lively foot traffic too!

After a great dinner, we got back to the hotel and checked our email accounts.  To our surprise, we found out that the tour guide for our second walking tour messed up his schedule and did not show up!  That was alright – we got a good sampling of what the city had to offer.

Anyways, I hope you enjoy the photos in the galleries above!  This was a great outing to a city that I would visit again in a heartbeat.