TNL Travels- Chicago in a Day

I love to travel and I love a good road trip. They really are the best. I recently took a whirlwind trip to Chicago and it was fantastic. When I say whirlwind, I mean whirlwind. It was a Saturday to Monday trip, which meant being on the road for two days. So, essentially I spent a couple of nights and a day in Chi-Town.

In Toronto, Tai Pan Tours offers a number of bus trips to popular cities in both Canada and the USA. Their trips tend to be short and geared towards either shopping or sightseeing. The tours can be rushed and exhausting as they try to pack lots in. A friend once described them as driving though cities and stopping at landmarks only long enough so that everyone could get off the bus and take a picture. However, what I have learned is that the key to making the most out of these trips is to use the tour for transportation and accommodation. Then, when we arrive in the city we ditch the tour and do our own thing until it is time to head home on the last day. My friends and I have done this with NYC and Boston and it worked out perfectly. These tours are a great way to have an affordable mini getaway and get a taste of a particular city.

The Tai Pan 3 day Chicago tour was only $168 CAD (based on our triple occupancy) and included transportation and two nights accommodation at a 5 star Loews hotel. Pretty amazing, huh? The hotel was located near the airport (about 30 minutes from downtown) so we just used Uber cars to get us back and forth. Easy peasy. The hotel was also located adjacent to a convention centre that was hosting an anime event. This made for very good people watching.


Although my Chicago trip was quick, I got a taste of some of the sights and finds that I would recommend to anyone visiting the windy city. In true TNL style, I will be sharing my highlights in hopes that it may be helpful if you head to Chicago.

The. Pizza. So one of the most well known spots to get authentic Chicago style deep dish pizza is Giordano’s. My friends and I decided to do a later night pizza run and get this famous pizza. We hopped in a cab and arrived at Giordano’s to find out that there was a 2.5 hour wait for pizza. Ummm, what? No. It just couldn’t be that good. It was just too darn late, and we were too darn hungry for that scenario to work. So we sadly returned to our hotel. Luckily the concierge let us know of another resto called Angelo’s that would deliver a deep dish pie to our room. Hurrah. So late night Chicago style deep dish pizza happened. And it was delicious. As disappointed as we were about Giordano’s, I’m pretty sure pizza tastes better in the wee hours of the night.. .in sweats… in a hotel room than at a resto anyway.


So, deep dish pizza weighs basically the same as a small child. Check out just how huge this thing is.


It was fresh, dense and delicious with salty homemade sausage and oodles of cheese. Super filling, but well worth it. This is a Chicago must.

One of the most notable Chicago landmarks is the bean statue at Memorial Park. I have seen countless photos of people in front of and reflected in the bean and they always have massive crowds in the background. So, we knew that this would be a busy place and decided our best plan of attack would be to get ‘er done early. Turns out, although everyone calls this the bean , the real name for this art installation is Cloud Gate.

Cloud Gate is British artist Anish Kapoor’s first public outdoor work installed in the United States. The 110-ton elliptical sculpture is forged of a seamless series of highly polished stainless steel plates, which reflect Chicago’s famous skyline and the clouds above. A 12-foot-high arch provides a “gate” to the concave chamber beneath the sculpture, inviting visitors to touch its mirror-like surface and see their image reflected back from a variety of perspectives. Inspired by liquid mercury, the sculpture is among the largest of its kind in the world, measuring 66-feet long by 33-feet high.

We got lucky and our early arrival time paired with the on and off sprinkling of rain meant that cloud gate wasn’t too busy and we were able to snap some good pics.

CloudGate Cloud Gate

Jumping around in front of a ginormous bean is exhausting and as you can imagine, we were ready for some breakfast. I mean, it’s not like we had devoured the biggest pizza ever a mere hours earlier or anything…

We headed to Wildberry Pancakes and Cafe Restaurant just a short walk from Millennium Park. This brunch resto had been highly recommended and I was warned about long lines on weekends. We arrived at about 8:30 am and had to wait about 20 minutes for a table. Seems like this is a good time to go because when we finished and were leaving, there was a huge crowd of over one hundred people waiting to get in. Wildberry is super popular in Chicago as they feature local farm fresh ingredients and freshly baked breads. We feasted on a Mexicana skillet (farm fresh eggs, cheddar and jack cheese, chorizo sausage, jalapeno, avocado, cilantro and onions) as well as the signature Berry Bliss pancakes (vanilla crème anglaise, fresh berries and mascarpone). Winning choices, but I have a feeling all choices at Wildberry are probably delicious.


The bulk of our day was dedicated to checking out downtown Chicago on foot. We did some shopping, dodged the rain and explored. One of the best stops for this library nerd was definitely the Harold Washington Library. This massive main branch of the Chicago Public Library contains art exhibits, maker space (3D printer, software, and laser cutter), teen hub, music listening rooms, a scale model of cloud gate and a winter reading garden. We geeked out here for a while. Our only complaint was that they were sold out of library canvas bags for purchase.

987182792771457540_559700339    IMG-20150517-WA008

In the evening, we decided to make our way to Chicago’s well known landmark, Navy Pier. I was literally expecting to see a pier with some shops and restaurants, similar to San Francisco. What I didn’t realize was that the Navy Pier in Chicago is an entire contained complex .Navy Pier is a not-for-profit landmark originally opened as a shipping and recreational facility in 1916. Located on Lake Michigan, it has served many purposes throughout its rich history and currently encompasses more than fifty acres of parks, gardens, shops, restaurants, family attractions and exhibition facilities and is the top leisure destination in the Midwest, drawing nearly nine million visitors annually. Although it was under construction, the views were still lovely although it was difficult to get good pictures with all of the temporary fencing.

chicago from pier

I really wish Toronto would take a cue from cities like Chicago and do something similar with our beautiful waterfront. The Navy Pier contained both indoor and outdoor shops, attractions and restaurants. The only bummer? We arrived at about 7:30pm and the Pier closed at 8 (it now has later summer hours). So we did a quick walk around and wished we had started here earlier in the day. Still, I’m glad we saw it.

Navy Pier ferris wheel
My favourite part of the Navy Pier was definitely the breathtaking Crystal Gardens. The Crystal Gardens is an indoor, one acre, botanical garden. The glass atrium with a 50-foot arched ceiling holds over 80 live palm trees, lush foliage, hanging twinkle lights and dancing leapfrog fountains. The leapfrog fountains were so cool, ribbons of water that would fly though the air and land in a pool of water like a frog. Have a look at the arching fountain of water over me in this pic. I initially thought it was water passing through clear tubes. It isn’t. I know this because I decided to touch it and it sprayed everyone in my vicinity when I did. Oops.

Crystal Gardens

Before leaving the Navy Pier, I picked up some of Chicago’s famous Garrett’s popcorn. I was looking forward to this because I absolutely love the GH Cretors Chicago Mix popcorn that I’ve heard referred to as “crack in a bag”. While that the bag Chicago mix is tasty, this authentic version was the popcorn lover’s ultimate. This was without a date MY FAVOURITE THING I ATE IN CHICAGO. I am a popcorn fiend. Had I known what I was getting into I would have bought more. But, maybe its best I didn’t know. The Garrett Mix popcorn is a mixture of their Caramel Crisp (brown sugar and crème brulee crunch) and Cheese Corn (freshly melted, sharp cheddar). Guys, I know I get a touch dramatic about food sometimes, but this popcorn is bliss.

Chicago Mix

We had a quick mean at Bubba Gump Shrimp Co. as it was the only restaurant open later at the pier before heading back to the hotel.  I have seen Bubba Gump restos at some other cities I have visited and have always been curious as a seafood lover. Why is everything on the menu fried? I had a shellfish boil. Very much my thing, but truly the only non fried choice. Weird.


Overall, I really enjoyed my quickie visit to Chicago. I definitely plan to go back for a longer stretch to see more of the city (and stuff my face with more Garett’s Mix popcorn). If you have been to the windy city, please share your highlights in the comments so that I can add them to my Chicago to-do list!

Chicago night

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