10 Chicago Rooftops to Visit This Summer

I’ve said it before and I’ll continue to say it, rooftop season is my FAVORITE season in Chicago. Now, don’t get me wrong, I love Chi all year long, but, rooftop season – you just can’t beat it! (Maybe it’s because I’m from the midwest so rooftop season is a big deal to me, mainly because I can’t drink a cocktail on a rooftop or outside during the winter without freezing or being in a trendy igloo? I don’t know, probably.)

Anyway, I’m constantly asked what my favorite bars in Chicago are and aside from Three Dots and a Dash, the majority of my favorites are rooftop locations. If you didn’t know, River North is the neighborhood I visit most often so that’s where a lot of these rooftop locations are (or close to)!

London House Rooftop

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You guys! If you want one of the BEST views of the river, LH Rooftop is the place to be! Such a cute spot to mix and mingle while admiring the beauty of the city. Even if you’re only stopping by for one drink, it’s totally worth it.

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Small bites, indoor/outdoor seating, and cute decor. I’m a huge fan of the sea salt truffle fries here paired with a chilled glass of Prosecco!

Drumbar

Looking for trendy Instagram pics? Drumbar is the place, during the day, for my aesthetic. Stop by for a happy hour cocktail, a few Instagram pictures, and the chance to really soak up the sun. I highly recommend visiting during the day!

Cindy’s

It’s ALL about the views here. The drinks are good but the views are AMAZING. You’re overlooking Millennium park, you can see Lake Michigan, and bits of the city. My literal dream. Grab a cocktail, grab brunch, but ultimately make sure you take in the views!

Roof at TheWit

Looking for a place to take your bumble date on a first date? Look no further! This fabulously swanky, trendy rooftop is the place to be in the summer. Music will be bumpin’, cocktails will be crafted, and you’ll have the ability to overlook some of the coolest cities views in the loop!

Devereaux

If you’re looking for a spot for poolside cocktails, intimate ambiance, and some of the best tasting small plates – look no further! This chill rooftop located at the Viceroy hotel is one of my favorite places to really vibe out in the summer because it mixes the typical cocktail lounge feel with a splash of fun by adding the poolside as an option.

Apogee

The cocktails here are NUTS, like actually so cool! I’m all about experiences and Apogee delivers that for me. Highly recommend date night here!

Raised

I did an entire dedicated blog post about Raised so I’ll link that blog post here. It’s still one of my favorites and the truffle fries are still SO good!

Cerise Rooftop

I’m really into feeling like I’m in my own slice of paradise and Cerise is 100% a little slice of city paradise for me. It’s super hip, really inviting, and will make you want to stay until the wee hours of the morning just soaking in the city vibes.

52Eighty Rooftop Lounge

Located on the 52nd floor of the Cambria, this gold accented indoor/outdoor lounge holds a key to my heart! The ambiance is perfect for a casual night out in the city.

I’m always adding to my list of favorite places in Chicago so feel free to ask for updates or more locations! Happy sipping!

xx, Kaitlyn

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.

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

Gift Guide #1: Self-love

Happy December 1st! Can you believe that December 2017 is already here? Like, I’m still trying to get over the fact that 2005 was literally 12 years ago (who’s with me on that?). So, to welcome December with open arms, I’m kicking off the month with a series of themed gift guides for those special people in your life.

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Self-love is something that I take very seriously. I think it’s so important to take time out of each day to do something that fills you with joy, no matter what it is. Too often we forget to love ourselves first, we forget that we’re the only version of us that we’ll ever have. Mentally, physically, and emotionally, it’s critical to fill our souls with good energy. There are many ways to show yourself some good old self-love, I personally like to take time out of each day to decompress from the day and calm my mind. The best part is that, because there are so many ways to relax your body and mind, you’ll never have to fall into a stagnant routine.

One of the best ways to completely relax is to make a date with your favorite, local spa. I’ve had the pleasure of partnering with Mojo Spa in Wicker Park to bring some of the best deals of the holiday season to my readers. Mojo prides itself on their handmade soaps, skincare, and cosmetics that are made in small batches with good-for-you ingredients and formed into fun, creative designs! This Chicago-based beauty company has shared their ideals of merging beauty and comfort with celebrity fans and customers all over the globe. For over ten years they have been manufacturing, developing, and testing their own recipes! I’m all about handmade products that are made with fresh ingredients which makes this collaboration with Mojo a perfect fit!

I received my very own pumpkin pie bath soap, which is the cutest thing I’ve ever seen. The time, dedication, and attention to detail is just phenomenal! The best part about this soap is that it has anti-inflammatory benefits and is packed full of antioxidants.

With the holiday season in full swing, Mojo has launched their special Golden Ticket offer with any $200 in-store or online product purchase! A Golden Ticket could be anything from a $25 signature mani/pedi to 30% off products. This offer is only valid until December 24th so jump on this opportunity while you can!

If you’re a Chicagoland local, you can book a nail appointment at Mojo or stop by the store to pick up a few of their products. Gift sets are available for any occasion but especially for the holidays and at such reasonable price points. If you’re not local, no worries! They ship worldwide!

I am so excited to continue this gift guide series and I hope you are too! Other guides you should be on the look-out for include a gift guide for her, a gift guide for him, and a gift guide for the person who has everything! Happy Holidays!

xx, Kaitlyn

Rooftop Season

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Rooftop bar season is possibly my favorite time of the year, especially in Chicago. With so many unique, fun rooftops to choose from it’s often hard to pick just one! I’m here to give you in the inside scoop on one of the best I’ve been to. I classify best based on price of drinks, atmosphere, and view. Raised, one of my favorite rooftops in Chicago, is located just south of River North in The Loop district right on the river. As you can imagine, the views are absolutely killer!

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Raised has an upbeat, urban vibe complete with some of the friendliest mixologists around. One of the best things about this place is that there is an indoor section too so you can enjoy Raised all year long! Personally, I feel like this place is a hidden gem in the rooftop bar scene because, while steadily busy, it’s not overly packed like some locations are. Okay, let’s talk about the goods, the cocktail menu. Every signature cocktail on their menu creates a special euphoric experience hand-crafted for patrons to enjoy in good company. They don’t pay me to say this, I swear. My favorite is called the Jenever which is a beautiful blend of lavender, strawberries, lemon, and Bombay Sapphire – SO good!

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Next time you’re in the windy city make sure this place is on your list of go-to’s. Go get yourself a Jenever, an order of Truffle Frites (or any type of French Fries on their menu tbh), and grab a seat overlooking the Chicago skyline. Trust me, you’ll thank me later! Check out their Instagram page for more stellar views and pretty drinks (@RaisedBarChicago)!

What’s your favorite rooftop bar?

p.s. slightly embarrassed, slightly proud – this is me actually gawking at an order of the truffle fries I mentioned