Chicago, aka the Windy City, where stunning architecture, world-class art, and delicious deep dish pizza await!
We went on a weekend adventure to Chicago over the Easter long weekend in April 2023 (we actually got really lucky with the weather, it was sunny the entire time we were there!), and with it being our first time there, this trip was packed with lots of sightseeing and plenty of eating.
If you’re planning a trip to Chicago, here’s our itinerary to inspire yours!
Day 1: Architecture from the Sky and the River
We arrived in Chicago late at night and checked into the Pendry Hotel, a magnificent Art Deco building featuring modern, refurbished rooms. It’s in the perfect location; a block away from the Chicago River and only a short walk to the Millennium Park – right in the middle of everything. I’d highly recommend staying here or at least going to see the building as it’s stunning!
After settling in, on day 1, we kicked off our adventures with breakfast at Egg Harbor, setting the stage for a day full of adventures. Energized and ready to take in the city, we made our way to 360 Chicago, a must-visit attraction for panoramic views of Chicago’s skyline. To add a touch of sophistication, we indulged in a refreshing cocktail while enjoying the breathtaking 360 scenery.
I love going to viewpoints first; not only do you get incredible views of a city, but I find it helps me get my bearings of the size of a city and where I am located at that moment.
For lunch, we headed to Al’s Beef Sandwich, recommended by an American friend and it did not disappoint. They serve mouthwatering beef sandwiches (somewhat similar to Philly cheese steaks) in a casual takeout setting. This spot surpassed our expectations and was easily one of the best meals we had!
To appreciate Chicago’s renowned architecture, we went on the Architecture River Tour in the afternoon with Shoreline Sightseeing. Cruising along the Chicago River, we marvelled at the city’s iconic buildings and learned about their rich history and significance. This is a fantastic way to see the city and learn about the different buildings.
After returning to the hotel to freshen up, we enjoyed an early dinner at Labriola. Remember to make a reservation, as this popular spot tends to get busy. Even though we had a reservation, we still ended up waiting 20 minutes to be seated, so keep this in mind when making your plans.
With a menu featuring a fusion of Italian and American dishes, we enjoyed our first deep dish (albeit it a skinny dish) experience as well as spaghetti and meatballs.
After Labriola, we made our way to the Cadillac Theatre to catch the acclaimed performance of “The Book of Mormon.” This was of course another stunning building and the interior was amazing – and so was the show! We had seats in the Orchestra, where we managed to save over $100 USD as one of the seats had “limited viewing” (which was practically unnoticeable). Look for these type of tickets in order to save money on the theatre!
The night concluded on a high note as we enjoyed a nightcap at from a rooftop bar called RAISED, toasting to the unforgettable experiences of the day.
Day 2: Art, Parks, and the Original Deep Dish
Our second day began with plans to indulge in a pancake breakfast at Wildberry. However, the long queues changed our plans and we ended up in a little café where we savoured breakfast bagels to fuel our day of exploration.
Our first stop was Millennium Park, which is in the heart of the city. We strolled through the park, checking out the iconic Cloud Gate sculpture, also known as “The Bean.” Now, I will say that at this point, The Bean was very busy, and we did end up going back early the next morning, when there was significantly less people. Something to consider!
Craving a snack, we couldn’t resist stopping by Garrett’s Popcorn for their famous popcorn treats. With an array of flavours to choose from, this Chicago institution offered the perfect blend of sweet and savoury. We got cheese and salted caramel.
Next on our itinerary was the renowned Art Institute of Chicago. As an impressionism enthusiast and someone who studied it in school, I were thrilled to see so many famous works in person, especially Claude Monet, who is my favourite impressionist artist, among other remarkable collections. It’s well worth a visit.
Lunchtime arrived, and we ventured to Pizzeria Uno for a deep-dish pizza experience. Known for their authentic Chicago-style pizza, the 45-minute wait for the pizza to cook was well worth it. Remember to book ahead to secure a table at this restaurant, as it is known as the birthplace of deep dish and is very popular – we managed to snag a last minute reservation using OpenTable.
This was one of our favourite restaurants, the food and staff were great, as was the ambience and interiors.
After lunch, we indulged in some retail therapy at Primark and Target (I wish they were both available in Toronto!), then we walked along the Riverwalk, checking out some of the buildings we saw during the River Tour.
Returning to the hotel, we succumbed to a food coma (lol) after our meal at Pizzeria Uno. In the evening, we opted for a sunset stroll, followed by drinks.
Day 3: Farewell to Chicago
On our last day, we had brunch at Robert’s Pizza and Dough Company. We got a brunch pizza (because why not, when in Rome etc.) and cocktails. The dough was light and crispy.
To conclude our adventure, we hopped on the Blue Line to O’Hare and bid farewell to the glorious city of Chicago. The train to the airport is quite long (about 45 minutes), so give yourself plenty of travel time.
Tip: Get a CityPass / C3 Pass
If you’re planning on doing a lot of sightseeing, I highly recommend getting a CityPass (or in our case, a C3 Pass). The C3 Pass was perfect for our weekend getaway, and included the three attractions I wanted to visit: 360 Chicago, Architecture River Tour, and the Art Institute of Chicago. You save some money if you opt for the pass rather than booking/buying individual tickets.
Wrapping up on Chicago
Chicago truly surpassed our expectations. This magnificent city, with its stunning architecture and mouthwatering pizzas, proved to be an ideal destination for a two-day escape. Whether you’re an architecture enthusiast, art lover, or simply a foodie, Chicago is the perfect city to explore.
Shannon Purcell 
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