A Memorable Memorial Day Weekend

Turns out planning to have your wedding on a holiday weekend is pretty convenient for quick anniversary getaways. This past weekend was our first wedding anniversary. We got married in Chicago last year and decided to spend the weekend back in the city. I’ve been wanting to get back into blogging so I thought this would be a good place to start.

We hit the road Friday afternoon and made to downtown Chicago around 6pm. We lucked out and didn’t have any major construction or traffic delays. We have tried several different hotels in the city and this time was no different. We opted to stay at The Conrad, just off Michigan Avenue.

In addition to the fantastic location, the staff, room, and amenities were top all notch. Every employee we encountered was polite and greeted us or wished us a great night as we left for dinner. Upon checking in, I was asked what we had planned for the weekend and just told them we were celebrating our anniversary and didn’t have much on our agenda. Shortly after getting to our room, we received a knock on the door and to our surprise, the staff sent up a bottle of prosecco, chocolates, and a hand-written note. Touches like this are very memorable and set the Conrad a part.

We’ve been to Chicago numerous times and therefore skipped all the tourist activities. The fun part about the city for us is trying new restaurants and finding cool bars along the way. This time we tried several new places including, Tao, Barton G, Three Dots and a Dash, Kaiser Tiger, and Stan’s Donuts. In an effort to keep this somewhat short, I’m going to bullet my thoughts on each place below.

Stan’s Donuts:

  • Went early Saturday morning, I love being up in the city before everyone gets out and about

  • Huge selection of fresh donuts, we tried three different kinds and all were amazing, including the vegan cinnamon sugar

  • Their cold brew coffee is my new favorite

  • I plan to go here every morning I’m in the city from now on


  • Cool, trendy, all the vibes, instagram worthy

  • Drinks were creative and decently priced

  • Food was okay, nothing special

  • I’d recommend for an occasion but don’t know that I would go back tbh

Kaiser Tiger:

  • Gastropub in the West Loop. Their slogan is “Sausage, Bacon, & Beer” which pretty much sums up the place.

  • Big outdoor patio and beer garden

  • The food was so delicious. We had schnitzel, pork, cheese brats, and a beer bacon brat

  • Bloody Mary’s are spicy and strong, if that’s your thing

  • Glad we stumbled upon this place after the Randolph Street Market

  • Highly encourage checking it out especially if it’s a nice day and you’re looking for a patio

Three Dots and a Dash:

  • Fun and funky, if you can find it. Hint: the entrance is in the alley

  • If you’ve dreamt of an immersive luau bar in a basement, this is the place

  • We tried three different tiki drinks, all of which were good but filling and sweet

  • I will definitely go back to try some more drinks as well as their food

  • Make a reservation, we didn’t and it was standing room only

Barton G:

  • Quirky and over-the-top, very instagramable

  • Food and drinks were good but you’re paying for the crazy presentations which are honestly the whole point we went

  • The restaurant itself leaves a lot to be desired, the décor is boring and not what I would expect for the prices

  • Try it for a birthday or some sort of celebration as it’s fun with friends

Overall it was another great trip to Chicago and a special one being it was our first anniversary. We are already making a list of places to try next trip. If you have any suggestions, please let me know!



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