This past November, Adi and I booked a weekend trip to Chicago because a) the man really loves to travel, b) flights were cheap, and c) it worked with both of our schedules. I was particularly interested in The Windy City as I have heard amazing things about its architecture, museums, and food. We managed to snag a good deal on plane tickets and booked a private room at a budget-friendly Airbnb. With transportation and accommodation taken care of, the days leading up to the actual trip was spent figuring out how we could see/eat the best of Chicago in 72 hours.

Day 1

After we landed at Chicago Midway Airport, we bought Ventra cards and loaded 3-day CTA unlimited ride passes — a convenient option for getting around the city and an absolute must, in my opinion. Riding the L-train is an unique experience in itself, as you get to meander along the cityscape and see the nooks and crannies of each passing neighbourhood.

As soon as we checked into our Airbnb and dropped our bags off, we hit the ground running. Our first mission was trying the iconic deep-dish pizza. There were numerous options but we decided to go with Lou Malnati’s, a chain restaurant with a big reputation. We had to join a waiting list to be seated and once we ordered, had to wait another 30 minutes for the pie to be made. But the wait was definitely worth it — my tastebuds fell in love at first bite.

I recommend:

Day 2

The next day we headed to one of the city’s best attractions, The Art Institute. Pro tip: buy tickets in advance online and you won’t have to queue in a ridiculously long line. We spent a good part of our morning exploring the numerous exhibitions — there’s bound to be something for everyone. Afterwards we headed to Cloud Gate which is a nice place to take selfies and people watch.

As we were visiting Chicago near the start of the holiday season, we were able to check out Christkindlmarket at night. There were vendors that sold authentic German eats such as pretzels, currywurst, roasted nuts, among other things. Adi was the more adventurous out of the two of us and tried the pickled herring (I abstained from kissing him after that). We ate a low-key dinner at Portillo’s before heading to a live music bar, where we jived to old-school hits and even witnessed a proposal!

I recommend:

Day 3

On our last day, we hopped on a bus and headed north to Lincoln Park for a picturesque view of the city. The weather was finally cooperating and we were able to snap photos of Chicago’s famous skyline. We then walked around to the nearby Zoo and Conservatory. Despite being free, it never felt overcrowded and the indoor and outdoor enclosures allowed us to view a fair amount of animals. My favourite part was probably seeing the penguins! Spent a good five minutes watching the little one on the rock contemplating life.

As our flight back to Toronto was scheduled in the evening, we spent the rest of the day exploring Old Town and The Loop before making our way to the airport. With a bag of Garrett’s Popcorn in one hand and XXtra Flamin’ Hot Cheetos in the other, our short but sweet trip to the Windy City came to an end. I would love to return in the warmer months and discover new eats and sights outside of the city core. Until next time! 🙂

I recommend:

  • Taking a short detour to Chinatown to eat cumin lamb flatbread (omg so good!) at Xi’an Cuisine
  • Lincoln Park for a different view of Chicago’s skyline — also houses the Zoo and Conservatory (both FREE!)
  • Checking out the various FREE public art downtown

Bonus vlog footage:

Also! Make sure you check out Adi’s top 5 things to do in Chicago!

The Sum of our Chicago Trip

Our Chicago trip cost each person $ 544.95 CAD.  In all, I think we had good value for our money. We only spent this much due to:

  • Adi found a great deal on a flight to Chicago as we went on a randon weekend in November
  • For the most part, we never really splurged on food and got by on affordable, but satisfying eats
  • Chicago is a very affordable city to visit due to the numerous things you can see and do for free such as Millennium Park and Lincoln Park Zoo
  • Accommodation is cheap compared to cities such as New York and Boston
Categories$ (CAD)
Food & Drinks112.42
Second City37.37
Art Institute of Chicago34.54

pie chart of spend in Chicago trip



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