Trip planning is probably one of my top fav things to do. Right up there with sleeping and vintage furniture shopping. I pretty much love everything about trip planning (well, I guess minus the actual logistics/anything involving maps and directions..Bo can do that part.).. I really love digging into a new city/town/country and trying to uncover hidden gems to go explore in person. It’s pretty epic to find something online and then actually see it in person. I MOSTLY love the hunt for an awesome hotel, but I also really enjoy planning activities, finding cute restaurants and
searching for drinking the perfect cocktail. I always have great design in mind when I’m looking for places to check out.
Two weeks ago I headed to the windy city with some gal pals to celebrate our good friend Jill getting hitched! Before we went, I had an intricate itinerary full of awesome things to do, like check out the Van Gogh exhibit at the museum (or try get get a room in the Van Gogh Airbnb), or wander through the botanical gardens. Alas.. sometimes even with the best of planning you need to just go with the flow. And for us, that meant dancing until the sun came up and hanging out in bed eating pizza, rinse, repeat. haha. (PS, I wouldn’t have had it any other way!) This was the first time I’ve went on a big girls trip to another country and let’s just say we had the time of our lives- and I’ll just have to check out the art and cacti on my next trip ;).
We did end up checking out a few cool spots, so I’ll be sharing those below- alongside the little trip guide that I had *intended* to follow. Next time, next time. I 1 million percent plan to go back, it was incredible.. so if you have any hidden gems to share for round 2, leave them below!
This hostel is the BOMB.com Delicious coffee and wicked-cool decor. It was hard to get any great photos because of the ambient lighting- but if you’re in Chi-town this place is on the must-see list. It’s an adorable hostel decked out in morrocan rugs, wall tapestries, + giant comfy blue sectionals. So much coolness packed into one place. Yes, I said coolness. For your information, circa 2003, my email addy was email@example.com. Brap! Also, I should mention the coffee was SO GOOD. Also, this hostel publishes a weekly blog post with things to do, which is super great if you’re visiting the city. Two days before we got there they had someone in taking aura photos.
“We make polaroid photographs of you and your aura. We come to you.”
Ginos East Pizza
Ginos East was f*@$ing awesome. First of all, the deep dish pizza was pure heaven. You have to wait like an hour for it to be made, but it’s worth it. Not only is the za SO good (We split the small deep dish pizzas, we got two for four of us- and it not only kept us full for the entire day- we had leftovers for dinner. Literally, we only ate deep dish pizza one day. It’s like a 10 course meal.) From the outside, it looks like any other Chicago pizza joint- brick walls. Red and green street sign. As soon as you step into the place, BAM! Black walls with white graffiti covering every inch of the place and it’s SO COOL!
Parlor Pizza Bar
Neapolitan-inspired pizzas prepared in imported Italian Pavesi wood-burning ovens. Um.. Ok!
Lost Lake Tiki Bar
A stylish tropical oasis-meets-flotsam strewn island hut, Lost Lake evokes both the glamorous tropical escapism of 1930s Hollywood and the rugged nautical, island aesthetic of the world’s first tiki bar — the original Don’s Beachcomber Cafe. Banana Leaf Patterns + Neon signs are my kryptonite.
So this is a bar we actually DID make it to. (Woop woop!).. I must admit though, it looks a lot cooler than the drinks taste haha. If you’re looking for a cool vibe, this is definitely the place. If you’re looking for drinks that taste good.. mm, not too much. We each had drinks off the painkiller menu.. which we all joked should be called the pain-starter menu.. I know.. we’re comedians. Anyways, if you can plug your nose and push past the incredibly strong drinks, you’ll have a great time drinkin’ out of skulls and seahorses. Cool! (BTW, to get into this watering hole you have to go through a sketchy dark alleyway. It looks way more badass from the outside.. until you walk in to tropical tunes and coconut everything).
Another spot on the list we didn’t make it to. In the 1920’s, the trenchermen building opened as the luxor russian baths. through the middle of the century, the place remained a spot to steam, grab a drink and have a bite. Inspired by this idea of a meeting place for the community, trenchermen was born in 2012. I’ll gladly drink rose by the glass on that blue tufted beauty. It’s on the list for next time!
Patio Must Sees
RM Champagne Salon
Ahh, the Champagne Salon. This was a high priority for me, but it unfortunately was juuuuust out of walking distance from our hotel and we would have needed a cab- so we opted for something a bit closer. Their IG account description goes: Champagne. Burgers. Cheese. Patio…I can already tell we are going to get along just fine and I will certainly be back. (Arny voice) Did I mention the word Champagne is in the name of this miraculous place? I am praying that their Parisian-style oasis patio is open for my next trip!
J Parker Rooftop
I love me some rooftops. Enjoying drinks on a roof is just so much more fun. Sitting proudly above the Hotel Lincoln (cool hotel alert), the J. Parker offers the most spectacular views in all of Chicago. They serve a cocktail called liquid sunshine, and that to me sounds like happiness.
See you on the roof!
The Doughnut Vault
One thing we did, and we did well.. was go dancing- and for us, Howl at the Moon was our jam. You know when you go somewhere new, and you love a spot, so you just keep going back? Yeah.. that was us. We loved this place and we had a riot. If you’re into piano battles and old-school-jams- you’re going to want to bring your dancing shoes.
If you’ve got any amazing Chicago must-sees- leave them below and I’ll add them to this list. I promise there will be many more photos next trip! Thanks for reading.