Chicago. Wow.

Most definitely, hands down, one of my favorite cities in the US.

For those of you don’t know, I was born and raised in Chicago. Well — born in the city, raised in the burbs.

My mom and dad grew up just a few blocks away from each other. They both attended catholic schools — all girls and all boys — and were grade school sweethearts if you can believe it.

Cute, right?

Once I popped into the world, my parents decided they wanted somewhat of a different life for their own family. They felt the city wasn’t a safe place. So, they moved to the suburbs. Me, my mom, my dad and my soon-to-be little brothers.

Once I hit junior high, my dad got an itch to move really far away. Like across the country far away to an even safer and more remote place — Washington.

14 year old Cortney was crushed. How could she leave her friends, her family and her life all behind? And why on earth was her dad so adamant about being around mountains?

Luckily, my dad gave in a little and let me finish high school before we picked up and left. But then, we were off. The fam went West. We left all of our family and friends behind and headed to a state where we knew no one.

But I always knew I’d be back — very often. And as I get older, I find myself going back more and more frequently. Getting in those visits. Experiencing the city I craved as a young child and now as a still curious adult.

My heart belongs in Chicago. It is sweet, and it is home.

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So here it is — my official Chicago Travel Guide. Created from my eighteen years of habitat and ten recent days of field research :).

Enjoy!

xx

 

Chicago Travel Guide

WHERE TO STAY

Kimpton Hotel Grey

Whenever traveling to a new city, I seek out Kimpton hotels first. Their group is one I simply trust. Modern design, plush furniture, hip offerings and the best locations. This hotel choice is an obvious 🙂 gray / grey. It’s new, located in the Loop with walking distance to the sites and shopping you need for your visit and has one fabulous terrace for evening drinks and mingling.

The Robey

This hotel was created by renovating two historic buildings in the heart of Wicker Park. Rooftop bar, pool and loft rooms available for booking — this hot spot should not be overlooked.

The Alise Chicago

Located in Millenium Park is The Alise Hotel — historic charm, modern interiors and those boutique vibes you’re seeking. Part of the Staypinneapple group — the hotel is cost effective and has some fun stories behind it. Room 809 is said to be Al Capone’s denistss office where some shady mob ish used to go down. The Art Institute and theatre district are right next door too — options for your days and eves.

Hotel Lincoln

This “modern speakeasy” hotel is located near Wrigley, the Zoo and DePaul, giving you a taste of Lincoln Park. It’s part of the Joie de Vivre hotel group and is full of eclectic charm. Go here for boutique pricing and midwest charm from the staff.

Hotel Godfrey

I’m basing this entirely off reviews and the amazinggg rooftop bar/club I spent a couple of hours working at — but this hotel is chic, modern and right in the popular River North area, around restaurants and watering holes galore. Stylish, contemporary rooms in a building that (to me) resembles the Standard High Line in NYC.

WHERE TO EAT

Lonesome Rose

Located in Logan Square, this last minute dinner find did absolutely not disappoint. Creative Mexican / Tex-Mex fare — wooden warehouse interiors with plant and mirror decor, trays in which your food gets served and the best house made spicy marg I’ve had in awhile. Added bonus? There’s a speakeasy downstairs. Chyea!

Beatnik

Throughout the entire duration of my recent stay, my friends were saying over and over how much I would love this place. I missed the chance to go to brunch during the first weekend, but on the second, we made up for it by doing a girls dinner there. And oh. my. GOD. was it cool. Plants everywhere, disco house beats (swoon), amazing shareable plates and servers that scream ultra-hip vibes. The design of the space was inspired by the bohemian lifestyle and aesthetic sensibility of the 1950s in America and Europe — ummm cool right? I’ll be attending this place for sure every visit back. Go. Now.

The Hampton Social

Since we’re talking about the coolest places ever — we must talk about this precious place. From the moment you walk through the doors, you feel like you’re in the north east among hamptonites in their white cropped denim and striped or chambray tops. Rosé all day is a must here — so much it’s written on the wall in the most beautiful light fixture. Chat, mingle, eat bites and stay awhile in this well-let, energetic space. It’s addictive and I did not want to leave.

Beatrix

My family and friends just get me. The fam made dinner reservations for my arrival at this beautiful restaurant located in not one, but three locations (I found this out the hard way) with market locations in addition. The vibrant eclectic space is perfect for all day eating and drinking. Great wine list, a plush variety of food offerings and a cafe corner for your sweet treat needs.

Green Street Smoked Meats

Who says you can only get Texas-style smoked BBQ in Texas? This West Loop gem offers everything from brisket to short rib to rock music. Dim lit and oh so cool for a bite and a cocktail.

Summer House Santa Monica

One sunny, airy and instagrammable atrium space serving New American fare — this spot has been recommended to me every time I visit Chicago as it screams West Coast (best coast) vibes. Located in Lincoln Park, it’s a must visit amongst wandering this super cool neighb.

3 Arts Club Cafe

Though I didn’t get to make it during this visit, this posh spot was recommended to me by a fellow blogger and I can see why. Posh interior meets garden club. Coffee, cafe snacks… a wine bar. You can’t go wrong with this spot. Take a break from shopping in the Gold Coast by coming here for a libation and bite.

Etta

Italian newness and goodness. I had the chance to try at least half of the menu and I can tell you it’s effing BOMB. Head to the rooftop for a cocktail pre dinner and definitely say yes to any suggested apps.

Aba

Mediterranean. Rooftop. Greenery. Chic. Such good vibes (and amazing food) at this Fulton Market District gem. You’ll want the round room with it’s own chandelier and a ton of shareables with friends. 

Beach House Social

Good vibes. Good menu for drinks and eats. Rooftop. Plus wandering in Wicker Park is the epitome of cool. Break up your route by popping in here for some fun. 

Federales

Barbacoa style tacos say whaaat??? Yeah, get your taco fix here in this fun and lively gathering space. Do take a shot and do take their trolley to the United Center for a game.

WHERE TO DRINK

Cindy’s Rooftop

Another beautiful atrium that Chicago has to offer. Cindy’s Rooftop is such a gem — and I can’t believe it was my first time visiting during this recent trip. Located atop the Chicago Athletic Association Hotel, this bar and restaurant offers not only a great setting but one amazing panoramic view of Millenium Park, Lake Michigan and beyond. Grab some rosé for all day here.

Juice Rx

This company has two Chicago locations that scream contemporary cool. Wood and marble accents, açai bowls to smoothies to cold pressed juices. Guaranteed to make you feel like a million bucks after a night of dehydration if you know what I mean. I stumbled upon the Bucktown location amidst a morning run and wandering and was elated.

Big Shoulders Coffee

Did you know Chicagoans are referred to as “Big Shoulders”? Me either. Well, there’s a super cool, low-key coffee shop group with locations in downtown areas of The Loop, West Town, River North and Gold Coast. It’s a welcoming atmosphere that creates one damn good marshmallow latte. Give it a try.

I|O Godfrey

This was one posh rooftop find. Situated atop the beautiful Godfrey Hotel, is I|O — that offers beautiful views, chill beats, a damn good menu and the most beautiful white decor. You’ll pay a premium for the drinks but the vibes are all worth it.

The Allis

Whether you’re feeling like afternoon tea, a cold-pressed juice or an evening cocktail, this Soho House hangout is the spot. I ordered the Green Garden which was a mixture between juice and vodka — and it did not disappoint. Plus the chandeliers and people watching are worth the squeeze.

London House Rooftop

It’s true — with Chicago being one hell of a sweeping views city, you just want to be on top to enjoy it. London House hotel offers the coolest rooftop with a terrace bar, indoor dining area and just the most insane sights. You’ll feel like you’re floating above the city. Don’t pass this rooftop up.

City Winery

Because why would you not want to sip wines in the city while being entertaining by live music? Wine. The best. 

Goddess and The Baker

A serious healthy insta-gal’s dream. This should be on where to eat too, because everything is so damn good, but the Apple Butter Oat Milk Latte truly made a mark on my heart. 

 

 WHERE TO PLAY

The 606 / Bloomingdale Trail

Okay, this was like the coolest thing ever. After a long weekend I was craving a sweat, and so I decided to check out this abandoned railroad line that makes its way across Logan Square, Bucktown, Wicker Park and Humboldt Park. It’s modern design with interesting artwork makes it hard not to smile while taking a walk or run.

Wendella Boats Architectural Tour

The best way to learn all about the amazing city of Chicago — this original boat tour company takes you up and down the Chicago River — starting near the Magnificent Mile and meandering towards Lake Michigan and Navy Pier. Make sure to bring your camera (and a jacket as it can get windy).

Rooftop Hop Downtown

Seeking a fun itinerary for exploring a new city? Well why not do a rooftop hop! My girlfriend and I tested this out on the final day (as we actually missed the above boat plans). Get dropped off near the River downtown and take your pick between the selected options that the trusted publications of Eater, Timeout and Thrillist have to offer.

WHERE TO SHOP

You guys aren’t going to believe this, but I didn’t even make it shopping! Well, kinda not true — I did pop into Nordstrom for 20 minutes because, hello, Michigan Avenue Nordstrom. But the areas I was meaning to check out, I didn’t quite make it to. Sharing what I was intending to scope out for you — and will plan to update this once I go back :).

The Magnificent Mile

The most well-known and popular for downtown shopping — the Mag Mile. Anchored by three major shopping centers — 900 North Michigan Shops, Water Tower Place and The Shops at North Bridge. Prepare to be overwhelmed with options.

Wicker Park Boutiques

A little more laid back — this is where you can find boutiques all in a row. You’ll find more unique treasures and designer offerings (both up and coming and well-known). Be sure to check out Penelope’s for french brands, P.45 for the best curation of apparel and Gather Home and Lifestyle for cute home decor,

Gold Coast Shopping District

Including the high-end shopping area — Oak Street — this neighborhood offers you that elevated brock and mortar experience. Warby Parker to Restoration Hardware to BHLDN. The premier experience is here.

 

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Fin! Well, for now… :).

If you’re headed to Chicago in the near future, please be sure to reference this guide and do comment on anything I may have missed! I’ll plan to update as I visit in the future.

And if you’re seeking more travel guides, be sure to check out the growing library here, with LA coming next!

// cb ✌????