If you were looking for a tourist guide to Chi- town, then you are reading the wrong blog post. Everyone knows about Garrett’s popcorn, The Bean, Navy Pier, and Giordano’s pizza. What I have here for you is a guide to an Instagram worthy weekend in Chicago. We hit up some new places, and some old favourites, searched out the cutest walls, and have put together this guide just for you!

Sweet Mandy B’s

Let’s start with my new fave place. It was approximately a 20 minute (cheap) cab ride there, but it was well worth it. A place like this in Toronto would have been lined up out the door, but because the location wasn’t in the Loop, it was more of a local treasure than a tourist destination.

Sweet Mandy B’s is a photo worthy bake shop, whose sweets are as good as the décor. It is located on 1208 Webster Ave, and although we took a cab, we ended up taking transit back to our hotel with ease. Surprisingly, the take out part of the shop was far more busy than the dining part. I was so worried that we would go all that way and not have been able to get the shot, but I was pleasantly surprised. Clearly, the shop does well for locals, because there was a nonstop lineup of people waiting for their treats to go!

The food was delicious, the staff was lovely, and the décor was on point. I would 100% go back to Sweet Mandy B’s, and highly recommend that you put it on the top of your list!

The Hampton Social

The Hampton Social is an old favourite that we just had to visit again. However, even though it was winter, the place was jam packed like a patio on the first day of summer. Simon and I grabbed drinks and sat at the bar, as we debated what to do. I knew that I wanted a photo in front of their signature “Rose All Day” sign. I patiently waited, and finally a table was open.  I used my Canadian charm *we’re from Canada and we love it here and I just want to steal the table for a photo!* It worked. The lovely staff allowed me to snap some pics while they were so kind and patient with us. There is also another Instagrammable wall there, in the more nautical part of the restaurant, but it was way too packed to even try.

Pros: Lovely and attentive staff, stunning Hampton’s style vibes and décor, great food and drinks, and easy to get to.

Cons: Always busy, so make sure you go as soon as they open for the best photo opportunities.

Location: 353 West Hubbard Street

Sugar Bliss Patisserie 

Sometimes the best locations are the ones that you accidentally stumble upon. We were on our way to dinner that my mom had planned, when we walked by this pink gem! It was super close to our hotel, and was located in the iconic Palmer House (more on that stunner below). I made sure that we took the time to see this place the next day.

Their specialty is macaroons, in every flavour! They were perfection, and they also had a ton of other sweets too! We got there right before a huge rush, right after this photo it was packed full! This location is convenient to get to, and it is a grab and go quick stop! I would for sure return to this hidden gem.

The Iconic “Flamingo Wall”

I had heard of this wall, and seen photos before, but had never ventured out to find it! This was again, a happy accident of finding it. I wasn’t wearing my trusty pink coat at the time, so we went back to it another day. It is located at 601 N. Wells Street at none other than the Flamingo Rum Club (we did not go inside). If you like all things pink, then this wall is a must! For the best shots, go all out like my champ of a husband and take it from across the street. Bless his heart for dodging all of the traffic.

The Palmer House

All credit goes to my mumsie on this one. The Palmer House is a historic hotel that has been taken over by The Hilton, but has kept most of the renaissance charm of the building. If I were to guess, I would ballpark that there must be 75 rooms (aside from the hotel rooms) in this place. I mean, it has MULTIPLE ballrooms. Ballrooms. Plural. If you feel like getting lost for a while, you have to come here. We saw our magic show here in one of the rooms, and did some exploring along the way. If anything, you have to at least go up a couple of floors and just take in the ceiling, a work of art on its own.

It’s located in the loop, and is free to go in and look around (as far as I know, I mean we didn’t get kicked out so I think you’re safe).


That’s it for this trip to Chicago (let’s be real, we go like twice a year). When we come back, I already have some summery places in mind that I want to try, an of course we will return to our old favourites. Let me know if you enjoy my Instagrammable location blog posts like this! Would you like to see one for Toronto, London, or anywhere else that we frequent? Until then, happy travelling! XO