Guide: Friends Weekend in Chicago


Hi Loves,

There is something to be said about traveling to a place with your ride or dies. It reawakens the soul and leaves you with memories that will last a lifetime.

Since Bryce and I visited Chicago last year, we have been itching to go back. It’s one of my favorite cities on earth because my best friend lives there. Each time I go, it feels like my home away from home. Chicago is also a place where midwest mannerisms are still a thing and the city does a nice job of keeping downtown fairly clean.

If you are located in the midwest, Chicago is the perfect weekend getaway. Flights are typically cheap and you can find a relatively affordable hotel near the hotspots in downtown. It’s also a great city to explore with friends because it’s easy to get around and there is so much to do.

Here’s a glimpse of everything we experienced over the weekend along with the details of where we stayed and ate.


We stayed at the Selina Hotel & Hostel. It was less than a two minute walk from Michigan Mile otherwise known as Magnificent Mile. The rooms were relatively nice, however if you end up staying here, I would suggest bring your own compact mirror to get ready with. Quincey and I both decided that the lighting situation in the rooms were not the best.

I did love how the bottom floor was a co-working space. They even had a small vintage store in the lobby instead of a cheesy gift shop. Quincey picked up a really cool vintage Chicago Bulls t-shirt from the shop.


Dinner at Gilt Bar
Dinner at Club Lucky
Homemade cavatelli pasta from Club Lucky

Gilt Bar: This place feels like it is straight out of a movie. They are also known for their martinis and basement photo booth. I would show the photos from it — but they are little too promiscuous haha!

Club Lucky: Ian had talked about this place for a while, so we obviously had to go check it out! The hype was real. If you venture out to Bucktown, add this restaurant to your list.

Beatnik on the River: Bryce and I ate here last time we visited Chicago and LOVED it. The atmosphere was really cool and it’s literally on the river. If you are visiting Chicago for the first time, I highly recommend this place.


Pre-dinner drinks at the Berkshire Room
Quincey and Andrew at a bar near Wicker Park

The Berkshire Room: Bryce and I loved this cocktail lounge so much when we visited last year, we had to come back again. Their menu has a dealer’s choice option where you can pick the glass your drink comes in, the alcohol and flavor notes. It’s located in the ACME hotel.

Violet Hour: Violet Hour is a speakeasy/cocktail lounge located in Wicker Park. Their drinks were incredible and the perfect place to chill for awhile. The tables felt very private and secluded so you could easy have a conversation with someone without it being too loud.

The Bars in Boystown: “Northalsted (also known as Boystown) is one of the most country’s inclusive LGBTQ+ communities and the oldest officially recognized gay neighborhood in the United States. It’s known for its welcoming vibe, nonstop nightlife, LGBTQ-owned businesses, and excellent dining options. It’s also the center of some of Chicago’s most popular events and festivals.” – Choose Chicago

Bryce and I had been wanting to visit Boystown for a while, so I’m really happy that we were able to experience a night out there. It was so much fun!!!


Shopping on Mag Mile: As touristy as it may be, Magnificent Mile really is magnificent in regards to shopping. They have everything from The Real Real to Tom Ford and Aritizia. A few streets over you will find stores like Urban Outfitters, Vans and Dr. Marten. A shopping day here is a necessity if you are visiting.

Walking Around the Million Dollar Brownstones: After your shopping day is over, closer to the beach – yes, there is a beach in Chicago, there are incredible million dollar brownstones. Bryce and I spent so much time walking through the neighborhoods picking out our dream home. If only the owners would let you come inside and tour them!

Exploring Wicker Park: Ian and Claire live near Wicker Park, so we took the sky-walk/path there for the day. There is a ton of unique stores and vintage shops. Not to mention, they have one of the coolest Walgreens I have ever seen. It’s in an old bank building and the vault is now where they store vitamins.

Visiting the Starbucks Reserve: On our last night in town, Bryce and I grabbed a late dinner and walked to the Starbucks Reserve. It’s located on Mag Mile and is hard to miss. The building is made up of 4 floors and has a rooftop deck. On the top floor, they have an awesome cocktail bar with some of the best espresso martinis I have ever had. Keep in mind that there is almost always a line to get in. Pro tip: The later at night, the better and less of a line. We went on a Sunday evening and the vibe was so chill.

Trips like these are always good for the soul. I would love to hear about your favorite spots in Chicago. Message me and let me know!

Until next time, Spread Kindness.



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