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What to Eat, Drink, See and Do in Chicago

Hello everyone, if you follow me on IG (shameless plug- @thedianaediton) then you would have seen that I went to Chicago for 4 days a few weeks ago. I've been to Chicago before and my first ever blog post was about Chicago, so here's an updated version of it!

Firstly, getting to Chicago is easy- you can drive (about 10 hours) or take a flight from either Pearson or Billy Bishop, and land at either Midway or O'Hare airport. Whatever you choose, there are tons of options available to get to the windy city.

For brunch, hit up Wildberry right next to Millenium Park but be warned- there will be a wait. We waited an hour to get there on a Saturday but it is 100x worth it. I went there during my last Chicago trip and am so happy that we went back. It's not expensive, there are tons of options for food, it really fills you up (no one was hungry until 8pm, and we ate at noon) and it's delicious. I know that I will continue to come back to this brunch spot every time I visit Chicago.

Deep Dish Pizza
Essentially there are two main spots for the DDP (heheh, get it?)- Lou Malnati's or Giordano's. I ate at Lou's both times, but truthfully, I'm sure I wouldn't have minded one way or another. Deep dish pizza has a great crispy crust and is loaded with cheese and whatever other toppings you add on, you eat it with a fork and knife and it's way heartier and filling than thin crust pizza.


Very stereo-typical Chicago place, overlooking Millenium park where you can go for food or drinks and sip them on the standing patio. A great vibe and it's located on the roof of the Chicago Sports Club, a great place to venture within and see how it plays homage to old time 1920s (30s? 40s?) Chicago. This is where you'll get gram worthy pics.

I went here last time with my sister and loved it- it's a speakeasy so it's super hidden, you wouldn't know that there's anything there except for the fact that there's a line up outside of just a plain building. It's not so much a dinner place, rather just a drinks place and it's extremely dark, so pictures aren't a possibility. It's located in Wicker Park which is slightly north than downtown, but still well worth the trek over, either via uber/lyft or transit (there's a subway stop right in front of the bar!)
This speakeasy specializes in original and fancy drinks and it's a very secluded and private place to bring your date too.

Situated right smack in the middle of the city, a rooftop bar that overlooks the river and is right in the middle of the high rises so that you're a part of the architecture. It is a small patio so be prepared to be slightly squished, and as such, I wouldn't necessarily recommend you coming here for food- rather just a drink and the view. The reviews on Yelp are horrendous 

We didn't end up going to The Signature Room as the craziest fog came into the city, but this is yet another roof top bar however this one is situated slightly further back in the city, so you get more of a view as opposed to London House, where you're right in the middle of the city and with the most perfect view of the river flowing in the middle.


Millenium Park
Great for a stroll so that you can see the ever famous and iconic Bean, and Buckingham fountain which is so beautiful!

Navy Pier
Keep your walk going and hit up Navy Pier where they have Saturday night fireworks (what we wanted to view from the Signature Room Bar before it was cancelled) but you can hit up the ferris wheel (expensive, but it gives you a great view of the city) and potentially a gram pic or two. I did this when I went to Chicago the last time, but wouldn't pay for it again.

Chicago Cultural Centre
The centre is located right by Millenium Park and they offer free tours (not even any tips at the end), so if you enjoy history and learning about a place, this was well worth it. The centre also includes the largest Tiffany's glass dome and OMG it is insanely beautiful. We stayed there for about an hour, just taking in the beauty of it.

Within the centre, you're also able to do free walking tours with guides (again, no fees or tips at all!) and although we didn't end up doing this, we spoke with one of the volunteers who was so friendly and said that the tours are based on what the attendees want, so if you have any recommendations the guides can cater to you- amazing.

Jazz Music
The city is the founding place of jazz, so you're sure to find some great live music. We were lucky enough to be there during the jazz festival and strolled along listening to some music. On the last day, we decided to go to a jazz bar and were recommended one (I'm sorry, I can't remember the name now!) but there was a $15 cover. NAH MAN. We said, so we entered another bar with live jazz and it was INCREDIBLE and free. The singer made jokes, and did jazz variations of No Scrubs, Lollipop (yes, the one with Lil Wayne!) and some other pop songs and classic songs. Well worth the one drink I bought there.

Have you guys ever been to Chicago? I highly recommend it and am totally down to go back! It's a city that has a lot of similarities to Toronto, but the people are much nicer and the transit is much better.

Until next time

xx Diana
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