Hey there, Chicago-lovers, night owls, and happy hour aficionados!

Put down your deep-dish pizzas and raise a glass to me as I take you on a tour of the finest rooftop bars in our beautiful Windy City. Come for the views, stay for the booze, and leave...well, when they politely ask you to exit because they're closing. Or when you've met someone who has a better condo view. Either way, it's a win-win!

First things first, we need to get one thing straight: if you've been hitting the same pub around the corner for the last decade, honey, we need to talk. It's time to climb that social ladder, quite literally, and embrace the high life - Chicago style. And by "high life," I'm not talking about that light lager your grandpa loves to chug on Sunday afternoons.

Oh, no, no, no! I mean indulging in artisan cocktails, sipping champagne, and noshing on exquisite bites, all while drinking in a sky-high panorama that'll make your Instagram followers so green with envy they'll look like a pack of dill pickles.

A Night Out in Chicago

Let's be real; a night out in Chicago is about as diverse as a box of crayons left in the sun - wonderfully melted into an unpredictable spectrum of experiences.

From the glamorous to the quirky, the vibrant to the tranquil, there's a rooftop restaurant in this town that'll float your boat, fill your glass, and maybe - just maybe - elevate your spirit. (See what I did there? ELEVATE. Rooftop. Get it? Oh, I'm just too funny sometimes.)

And let's face it; we're all done with 2022's "stay-at-home" trend. It's 2023, darling, and we've earned a bit of glam and glitter! We've got masks of another sort now, ones that involve cucumbers and 24k gold facials. So get off your couch, freshen up, and let's hit the heights of Chicago's buzzing nightlife! Come lounge at the outdoor seating, relax near the fire pits, enjoy the greenery, and admire Chicago’s skyline view. This is what living is about!

From the 24th floor to the 93rd, buckle up! We're about to launch into a skyward adventure of the best rooftop bars in Chicago.

From swanky downtown spots where the who's who hobnob to the hidden gems where you can kick back without all the pomp and circumstance, there's a little something for everyone. Grab your favorite pair of heels, dust off that blazer, and make sure your camera phone is fully charged.

You’re in for a delectable adventure that’s going to be a whole lot more exciting than whatever Netflix binge you had planned for tonight! Welcome to my airborne exploration of Chi-Town's intoxicating heights, where we’ll gaze at the Chicago River, the Magnificent Mile, and those gorgeous skyline views, all while sipping on a margarita, craft beer, or whatever bev you want.

Just remember: what happens on the rooftop stays on the rooftop...or at least, it doesn’t make it past my next blog post.

Stay tuned and hold on tight; it’s about to get breezy up here!

The Best Rooftop Bars in Chicago

Our first stop is a place where I swear the cocktails are as classy as the 1920s flapper girls, and the views are as stunning as Leo in Titanic — meet the one and only Cindy's!

Cindy's

Situated atop the Chicago Athletic Association Hotel in the Loop, Cindy's rooftop bar is the grand dame of them all. They might as well call it "Heaven's Patio" because, darling, the views from this place are downright divine. Grant Park, Millennium Park, and that big beautiful babe of a lake, Michigan herself, all within a cocktail's throw of your perch.

And speaking of cocktails, let's talk liquid assets. If your idea of a good time is a drink that's as complex as your last relationship, you're in for a treat! With mixologists who are more like potion masters, the cocktails here are a thing of dreams and possibly hallucinations.

My personal favorite is the "Love in the Dunes," a seductive blend of gin, honey, and a little bit of lavender magic. One sip of this, and you'll feel like you're drifting through a meadow in a Monet painting.

But wait, there's more! The food here is nothing short of fabulous. Their "Spirit Guide" charcuterie and cheese board is an absolute must-try. It's like a culinary tour of the world's best deli, right here in the heart of Chicago.

Cerise Rooftop

Next up, we're off to Cerise Rooftop, a nightlife hot spot nestled in the lap of the Virgin Hotel. Yes, you heard me right, the Virgin Hotel. Don't let the name fool you, though; there's nothing innocent about the wild nights and crazy memories waiting to happen up here!

Twenty-six floors up, Cerise offers a stunning 360-degree view of the city skyline that will make your heart skip a beat, or that could be the killer house beats from the DJ. Either way, it's an exhilarating experience. And when the stars come out, the mood up here transforms into an electrifying party that could give Gatsby a run for his money.

Their drink list is a cornucopia of unique creations. Take a wild ride with "The Witch's Backyard," a vodka-based drink with elderflower, lemon, and a touch of rosemary that's as enchanting as its name. Trust me, one sip of this, and you'll be cackling with joy.

LondonHouse Rooftop Bar

Our final destination on this sky-high tour of nocturnal delights is the renowned LondonHouse Rooftop Bar, located on the 22nd floor of a hotel on the corner of North Michigan Avenue and Wacker Drive. This tri-level venue boasts an indoor bar, an outdoor terrace, and what they call the Cupola — an exclusive, reservable space where you can pop the question or just pop a bottle of champagne.

The cocktail program at LondonHouse is pure poetry. The "Elysium Fields" with Japanese gin, peach, and yuzu is a citrusy, divine dream. You'll want to savor this one slowly, like a sunset or a particularly juicy piece of gossip.

The best part about LondonHouse? It’s open year-round. That’s right, Chicagoans, you can sip cocktails on a rooftop even when the snow is falling, enjoying American cuisine and signature cocktails. How about them apples (cider cocktails, of course)?!

Let's not stop there, folks! We've got a city that never sleeps and rooftops that sparkle brighter than a newly polished disco ball. Onward we go!

The J. Parker

Perched high above the Hotel Lincoln, The J. Parker offers some seriously Instagram-worthy views of Lake Michigan and the city skyline. Yes, those yachts you're seeing are real, and no, you can't swim over for a closer look. I asked. And don’t bother checking the weather. With a retractable glass roof, you’ll get the same glorious views, rain or shine.

Indoors, you're wrapped in a warm, modernistic charm that says, "Yes, we have great taste," and outdoors, you're greeted with a sprawling patio that’s just begging for you to lounge and sip. Go for the sunset, stay for the city lights, and leave...only when you've tasted their delightful cocktail menu.

With a twist on the classics, their craft cocktails are worth the trip alone. Try the "Bee's Knees," a sweet, tart blend of gin, lemon, and honey that buzzes right to your pleasure center. Pair it with their truffle fries, and you'll think you've died and gone to rooftop bar heaven.

Offshore Rooftop & Bar

Last but certainly not least, we have Offshore Rooftop & Bar, a place so grand it landed a spot in the Guinness Book of World Records as the world’s largest rooftop deck. Yep, you heard that right. It's not just a rooftop bar; it's a feat of architectural wonder.

Hovering over Navy Pier, this 36,000-square-foot venue gives you an unmatched vista of the lake, the skyline, and everything else worth seeing in the city. Think of it as your personal panoramic view of Chicago, one where you can order an "Aloha Felicia" (a deliciously tropical concoction of vodka, pineapple, lime, and passionfruit) without missing a beat.

And just when you think things can't get better, Offshore serves up an array of globally-inspired dishes that'll make your taste buds do a happy dance. The lobster roll is so good; it's been the subject of several dreams since I last tried it.

Honorable Mentions

Before we wrap this little rooftop rendezvous, a couple of honorable mentions are in order:

• The Robey: A cabana club in Wicker Park, this rooftop lounge has a more laid-back vibe.
• Kennedy Rooftop: At the Hyatt Place, this rooftop bar is a must-visit.
• ABA: A Mediterranean restaurant and bar located on Green Street.
• Château Carbide: Located on Michigan Ave, this swanky bar is a sushi and cocktail must-visit.
• Lonesome Rose: Near Logan Square, this Mexican rooftop bar takes tacos and Tex-Mex to the next level — literally.
• Rooftop at Nobu Hotel: Located near West Loop, this luxury hotel is home to delicious food and beautiful views.
• The Gwen: Located on Rush Street, The Gwen is an Art-Deco-inspired rooftop bar you won’t want to miss.
• VU Rooftop: Signature cocktails and spectacular views, this brunch and dinner spot is a must-try near South Side.
• Z Bar: A delicious restaurant and bar located on Superior Street in Streeterville.
• Cabra Chicago: This must-see is a Peruvian-inspired rooftop patio located off Fulton Market.
• ROOF on TheWit: Located off State St, this bar with a retractable roof will have you speechless.

That’s a Wrap

There you have it, my nightlife-loving friends - the top 5 rooftop bars in our glorious Windy City. From the cocktail connoisseurs at Cindy's to the record-breaking expanse of Offshore, there's something for everyone when you're ready to drink up the city from above.

The heights are dizzying, the drinks are strong, and the nights are unforgettable. Time to make some stories for Monday, folks! Cheers to a great night out in Chi-town!