I love to travel. And since it’s impossible for me to stay in one place for too long, I decided at the last minute to get away to Chicago for the weekend with Tee – whom you might remember from my Mediterranean Highlights series.

We chose Chicago for a few reasons:

  1. its proximity to Toronto – the flight is less than 2 hours, which is great for a sneaky getaway
  2. it’s often compared to Toronto and has a lot to offer in the way of architecture and cultural institutions
  3. we’d never been before!

We didn’t really have time to research flights and hotels, so we booked the trip with – one of the easiest ways to compare and book flights and hotels. And you save when you book the two together – crucial given the state of the Canadian dollar at the time we booked the trip 😉

We had a pretty loose itinerary of things we wanted to see and do (and you know they were mostly food-related). We got our hands on the Chicago CityPASS, which offered great value and line bypass for major tourist attractions, which were the focus of this trip.

Check out the video above to see what we got up to – and below, find our list of 5 things that every Chicago newbie has to try!


Cloud Gate – or ‘The Bean’ as it’s more commonly known – sits in Millennium Park, a public park surrounded by amazing landscapes, art and greenery. It’s quite the astounding sculpture – standing at a whopping 33 ft tall and made of stainless steel, it makes quite the backdrop for a great selfie! Cloud Gate is incredibly smooth with no visible cracks which is quite mesmerizing, especially when you go to the opposite side of it which overlooks the balcony – this side actually offers the best view, as it reflects the Chicago city skyline.


The Chicago Dog is quite the treat especially if you go to Portillo’s – a restaurant that is quite visually striking and somewhat of a sensory overload at first! There are a few locations across the city – the one that we went to was packed with both locals and tourists. We got the Hot Dog with all the fixings: mustard, relish, celery salt, onions, tomatoes, a thick slice of kosher pickle and a sport pepper all atop a steamed poppy seed bun. You can wash it all down with either a chocolate shake or a smoothie of the day! And if you really want to indulge, try the cake shake!


If you’re craving something savoury and sweet, you’ve got to try some Chicago-style popcorn at Garrett Popcorn Shops, located throughout the city. It’s a combination of both their flavours Caramel Crisp and CheeseCorn. Fun fact: this flavour was actually created by Garrett Popcorn Shop’s loyal customers – and not some freak accident 😉 The line up was long and didn’t show signs of slowing down with locals and tourists so you know it’s the real deal! Initially we weren’t sure if we were going to be fans of the mix but we became true believers after our first bite – my extremely orange hands were a testament to the cheesiness. It’s a great snack, and make sure to grab a souvenir bag.


This was one of those things that really has to be experienced to grasp a full appreciation of just how horrible this beloved local liqueur really is. They call it Malört face – the immediate facial reaction to having downed a shot of what seems to be the liquid version of a grapefruit rind mixed with something else equally as horrible whose aftertaste lingers on for a while. This liqueur is considered a rite of passage and a cruel joke for Chicago newbies – but it’s something you should definitely do to say you tried it. Make sure to have you camera handy for those epic Malört selfies.

See also: Getting screeched in in St. John’s, Newfoundland


We saved the best for last! If you like cheese – like really really really like cheese – deep-dish pizza is an absolute must. While there are several popular spots across the city, we opted to go to Giordano’s in Navy Pier. It was a 40 minute wait, but luckily we were able to place our order upon arrival so that the pizza was ready by the time we were seated.

We opted for the Chicago Classic: pepperoni, mushrooms, green peppers, onions and a boatload of cheese! The deep dish is quite the design – having the crust as the bottom layer and then the cheese and another layer of crust on top, followed by layers of veggies and meat, and lastly topped with the sauce. Make sure to capture that cheese-pull!

There seem to be two camps in Chicago when it comes to deep-dish pizza chains – either you’re a fan of Giordano’s or you swear by Lou Malnati’s. And let’s not forget that there are tons of local joints that serve up this lactose nightmare! We’ll just have to go back and try them all 🙂 If you have a favourite, or if there’s anything that we missed, let us know in the comments below!

Watch the video above for even more suggestions.

Subscribe to gunnarolla on YouTube and check back next week for more adventures!

This trip was sponsored by with assistance from Choose Chicago. Written with contributions from Tee. All opinions are our own.
Recommended Posts

Leave a Reply

Let's get in touch

Got a question or a project idea? Let's get in touch.

Not readable? Change text. captcha txt