Play Hard: Chicago

It’s no surprise that Chicago is my home away from home and I absolutely love experiencing new things the city has to offer. My friends know I’m the gal to go to for recommendations in the city and I thought I’d bring my list of favorites to life by sharing it with all of you!

Drinks and Eats:

Three Dots and a Dash – MY FAVORITE BAR EVER. It’s grown wildly popular for it’s underground (yes, you heard me, underground!) tiki theme and imported rums in the last few years so you’ll need to make a reservation but I promise it’s worth it.

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Pops for Champagne – We all know I love my champagne and pops definitely delivers the best selection of champs and cheese boards!

Raised Bar – I actually did an entire review of Raised Bar last year so I’ll link it here and let that post do the talking.

The Up Room at The Robey – I was lucky enough to collab with The Robey earlier this year and had the best experience at The Up Room! The views were incredible and the drinks were all hand crafted.

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Cindy’s Rooftop – Another place with a great view and trendy drinks!

LondonHouse Rooftop – Hellllooooo perfect view of the Chicago River! This rooftop terrace is one of the prettiest in Chicago to grab a drink and admire the beauty of Chi Town.

Cubby Bear – A typical bar located in Wrigleyville but perfect for a pre-Cubs game drink!

Quartino – Honestly, one of my favorite Italian restaurants ever. I love pasta and I love pasta even more if it’s fresh/homemade. Let’s not forget about their Lemoncello Martini!

Public House Chicago – One of my favorite stops in River North for not only a great brunch but for their boozy cake shakes!

Giordano’s Pizza – Don’t come for me, this is my FAV deep dish ‘za in Chicago and always will be.

Rosebud – A cute restaurant with some Italian flare in River North.

Beatrix – With a couple of locations in Chi, this is one of the best places for a girl’s Sunday Funday brunch! (my girl gang and I went to the one in the west loop!)

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The Q – I’m not a huge fan of BBQ but The Q always serves up some delicious southern ‘Q.

Hub 51 – A great, American classic restaurant where you can devour a burger and fries or a few cocktails!

Portillos – I hate hotdogs so I can’t personally vouch for this but everyone says Portillos is THE place to get a legit Chicago dog. The cheese fries are delish too!

Noyane – SUSHI and a view!

Velvet Taco – Theeee place to taco ’bout! Everyone loves Velvet Taco and if you go, you’ll see why!

Big Star Taco – Margs? Check. Family style tacos? Check. Multiple Salsa Options? Check.

STK – I literally loveeeeee STK. I recently visited the Las Vegas location and the food is literally always amazing. Slightly pricey but totally worth it!

Tavern on Rush – A chic, trendy place to grab lunch or dinner. Great for groups too!

Steak 48 – Another super good place to get a steak cooked to absolute perfection.

Goddess and the Grocer – Absolutely obsessed with G&G. Super fresh ingredients and so great for a tasty lunch.

Hampton Social – The best frosé in the game and the cutest vine wall ever! (also great for brunch)

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Summer House Santa Monica – Beachy vibes and great food.

Where to Stay? 

I’m partial to River North because that’s just where I like to hang out so most of my favorites are in that area! 

Acme Hotel Company – If you follow me on Instagram you already know I love this place with my whole heart. The vibes, the location, the staff, the cleanliness … everything is amazing! Can’t say I love it enough!

The Gwen – A cute, swanky hotel in close proximity to Michigan Ave and the River front.

The Dana – Adorable hotel complete with spa! Who could want more?

Moxy Chicago Downtown – a NEW hotel to Chicago. Similar vibes to that of Acme but located a little south of River North in the loop!

Where to Play?

Cubs Game – I’m a Cubs fan and have been since basically birth! So, I’m partial to a Cubs game but the White Sox fans know how to party too. Either way, you really can’t go wrong … but … Wrigleyville has my heart.

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The Bean – A Chicago classic attraction. Pro Tip: Go early before all the tourists get there … oops probably shouldn’t give away my secret 😉

Navy Pier – It’s always a good time at Navy Pier! River cruises, Chicago eye, the conservatory … all the best things in one place!

Lincoln Park Zoo – What better way to spend an afternoon?

Social 25 – A club in River North with an upstairs and downstairs. In my prime, I may or may not have danced on a table of two in the basement of this place.


I’m always updating my list of favorites in Chicago so don’t hesitate to ask me for more recommendations and if I didn’t cover something you wish I would have in this post, let me know!

xx, Kaitlyn

 

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