36 hours in the Windy City

Chicago Bean


One big city, so little time.

Friday 7:00 pm – And so it begins

We arrived in Chicago on a chilly Friday night.  As we made our way to the Allerton Hotel, I could see the entire city lit up by soaring hotels, historic high-rises and well-lit signs. Everything shined and twinkled as we drove down the strip (including every tree branch decorated with tiny white lights).


9:30 pm – Late nights call for big bites

After we settled into our hotel, we made our way to the RPM Italian restaurant. The reviews of this place pretty much sum up the entire atmosphere. It’s rated a four star for a reason. It was so delicious with so many choices from pasta, steaks and seafood – it was enough to please everyone in the group. Even though it was large, the feel of the restaurant was very intimate with great service.

Saturday 10:00 am – Rise and shine Chicago

Saturday we went for brunch at the Sunny Side Up & Coffee Shop where they had special breakfast options. Selections like breakfast nachos, french toast with sinful toppings and corn beef hash were just among the few tasty choices you could pick from. Trust me, everything tasted as good as it sounds.

12:00 pm – Sweet streets

After fueling our tummies, we planned to do the whole tourist thing and walk around the city. Of course, we walked down the Magnificent Mile and hopped in and out of shops. My favourite stop was Dylan’s Candy Bar. We do NOT have anything that compares to this candy store in Toronto.  Anyone who knows me knows that I’m a sucker for candy (but who isn’t?). Every section of the store was dedicated to different types of candy. Sour sections, gummy sections, toffee sections, chocolate sections, you name it – there was section for it. The best part? The staff at Dylan’s lets you sample the candy for free.


1:00 pm – Bean there, done that

So we continued to wander around the city, taking pictures of the magnificent buildings – some old, some new. Our next stop was “The Bean”. It was such a cool experience watching everyones reaction to the mirrored shape. Obviously we had to get pictures of it.


1:30 pm – Deep-dish diving

All that walking worked up our appetites, so the obvious solution was deep-dish. We decided to make reservations at the infamous Giordano’s. It took about an hour for us to sit but that’s the norm. Waiting gave us a chance to tour around the city some more. When we were seated, the pizza came quickly and it was deeply delicious! I had no idea what to expect, so when it came I was shocked at the size. The four of us could barely devour a medium pizza and we were trying to make room for dinner. After wandering around some more we decided it was time to change for our dinner reservations.


8:30 pm – Dine here

First stop of the night was The Little Goat Diner. This place was so cute inside and the food had a great spin on diner classics. Breakfast is served all day, the selection of “sammiches” (sandwiches) were endless and the desserts? Well, our biggest problem was trying to pick just one. I ordered the Los Drowned sammi along with the Goat Chilli Cheese Fries – I regret nothing.


9:30 pm – Pop goes Chicago

After polishing off our plates at the diner, we were off to RM Champagne Salon. Another thing Toronto needs to get on! Champagne salons are everywhere in Chicago but this was the one we were told to visit. When you walk in, the atmosphere is so laid back. It was a chilly night, so we warmed up in this intimate lounge with the fireplace going and candles lit everywhere  – it was exactly the place to hide from the cold. Behind the bar was an entire wall dedicated to different champagne glasses, all in different shapes and sizes. The rest of the decor was something to appreciate as well. Just by looking up you’d see different coloured tassels hanging from the ceilings, the walls were covered in vintage frames and in all four corners were comfy tufted couches with funky pillows. The menu had a full list of mixed drinks that suited everybody. Not just champagne but Manhattan’s, screw drivers and even some new spins on old classics. This is a place you definitely want to visit – even if it’s for the welcoming atmosphere. But of course, we weren’t done yet. On to the best part!

This is POPS Champagne, another popular champagne salon to visit

This is POPS Champagne, another popular champagne salon to visit

11:00 pm – What diet?

Shake Shack it is! I ordered the Jelly’s Last Donut concrete and it was everything I thought it would be and more.

Sunday 10:00 am – An eggsellent finish

On our final day, we filled up at a random breakfast spot near our hotel which I can’t remember the name of. But check out the pictures of some of the food we ordered. You’ll see the eggs Benedict on a quinoa tomato base, classic eggs with grits and lemon pancakes with orange zest sprinkled on top.

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12:00 pm – Just monkeying around

After breakfast, we took a Uber to the Chicago Zoo in Linkin Park. This place is free and packed with all kinds of animals like flamingos, zebras, lions, and cheeky monkeys. After the zoo, we had one last stop to make.

1:30 pm – Shaking things up one last time

Shake Shack: Round 2! We were behind on timing so we needed a quick bite to eat. The Shake Shack was the perfect choice since it was conveniently situated beside our hotel. Everything was delicious – the burgers, the hot dogs, the crinkle fries and of course, the chocolate milkshakes. We didn’t have much time to spare after that so we ran over to pick up our luggage at our hotel and then set off to the airport.


My take away from Chicago?

Even though we barely spent two days in this beautiful city, I felt like we saw a lot. The food was nothing short of innovative and delicious, the people were welcoming and the city itself was just so beautiful – yes even in the middle of winter. There’s so much character and each street we wandered down felt so diverse. All I can say is, Chicago is my kinda town.

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  • Reply
    March 16, 2016 at 12:29 pm

    Beautiful photos – love the Windy City!


    • Reply
      March 16, 2016 at 1:28 pm

      Thanks candy!! ❤️

  • Reply
    Anesha Sylvia
    March 16, 2016 at 1:38 pm

    The champagne salon sounds like it is totally ME! I would love to try a spot like that.

    • Reply
      March 16, 2016 at 2:01 pm

      You would love it!! It was amazing

    • Reply
      March 16, 2016 at 3:14 pm

      You would love it! One of the coolest cities I’ve been to for sure.

  • Reply
    March 16, 2016 at 1:56 pm

    Enjoyed the tour with you through your eyes.lovely pictures.

    • Reply
      March 16, 2016 at 3:14 pm

      Aw thank you so much! We had a blast

  • Reply
    March 16, 2016 at 8:20 pm

    ‘I regret nothing’ LOL pretty much sums up our diet that wknd!

    • Reply
      March 17, 2016 at 2:36 am

      Lol yup

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