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Take Your Love on a Romantic Getaway to Chicago

Chicago lesbian couple by the water

Queer hub Chicago has a steamy side that will warm your heart even when it's icy outside. 

It might be cold outside, but for those of us in the Midwest, winter is just another season to enjoy. That’s why my wife and I, who live in Milwaukee, use Chicago as a romantic getaway destination; it’s only 90 minutes away via Amtrak and with a bunch of options for steamy romance and adventure, you don’t even notice the freezing temperatures.

Chicago has been long been a historical queer hub, with a number of neighborhoods overflowing with gay bars — and the gays that make them what they are. For instance, the Northalsted section of the city’s Lakeview neighborhood holds the distinction of being the nation's first officially recognized gay village. 

But queer life, culture, and people are not confined to those areas alone. According to a 2018 Chicago Department of Public Health report, 7.5 percent of Chicago adults, or about 146,000 individuals, identify under the LGBT umbrella. Here’s where to stay, dine and play in the city to experience some of what Chicago so special. 

Royal Sonesta Chicago Downtown


Where to Stay

Intercontinental Magnificent Mile - Finding a hotel that’s comfortable, with a lux feeling, near everything and a great hotel is quite a feat, but the Intercontinental is the full package. The staff are overwhelmingly kind and helpful, although it was hard to find someone to assist with storing our luggage, that’s just nitpicking. But the star of the show is the Michael Jordan Steakhouse. This is not a hotel restaurant that you just eat at because you get in late, or can’t get a reservation. It’s worth a visit even if you don’t stay at the hotel. Don’t forget your swimsuits! The pool at the Intercontinental is marvelous. 

Palmer House - For old-school magnificence and charm, you’ll want to book a room at the Palmer House. The dim lighting, decorative high ceilings, and grand staircases hint at the hotel’s romantic history. The hotel was a wedding gift from Potter Palmer to his bride Bertha Honoré Palmer 150 years ago. Given the historic nature of the property, the slight peeling of wallpaper and tiny bathrooms can be understood, and even admired. For history nerds and couples that love the historical old Chicago ambiance, this hotel is the romantic destination you have been waiting for.

Royal Sonesta Chicago Downtown - You should book a room in the Royal Sonesta (pictured above0 just for the impeccable river view that’s downright breathtaking (although I wouldn’t suggest the city view due to the hotel directly across the street). A modern, recently renovated towering building, the Royal Sonesta hotel feels bright and lively. The room we stayed in was clean, comfortable, and welcome, and why not remarkable itself, the view takes a good room and elevates it to remarkable. The Royal Sonesta is centrally located, with dining, shopping, and entertainment just moments away. 



Chicago bar Nobody's Darling


Where to Dine

Nobody's Darling - The drinks at Nobody’s Darling (pictured above) are so good — especially the spicy margarita! A no-frills, Black-owned bar, Nobody’s Darling is dedicated to the outcast, and is clearly much different than your average “gay bar.” You’ll be welcomed by a massive rainbow flag, cheerful bar staff, and a comfy bar stool. The interior is brightly lit, a nice change of pace from the dim and sometimes uncomfortable vibe in many bars. Definitely worth a visit for drinks before a romantic dinner out, or, if it’s your kind of this, a bar outing all on its own.

Sun Wah BBQ - If you love duck, Chinese food, or (hopefully) both, the Beijing Duck Dinner at the winner of America’s Classics Award by the James Beard Foundation, Sun Wah BBQ, is a must-try. It’s not on the official menu and tends to sell out, so when you call to make your reservation, be sure to let them know that’s the dish you want. The Beijing Duck Dinner is served as a three-course dinner, starting with the cutting of the duck itself tableside. The sliced meat is served with steamed buns and accompaniments. The carcass is returned to the kitchen, where it will be transformed into your second and third course. You get an option of duck fried rice, or a duck noodle dish, and then an incredible soup to finish off your meal. 

The Dearborn - For a unique take on grilled cheese and fried chicken that’s bursting with flavor, head over to The Dearborn for lunch. Queer-owned, this bustling lunch spot has unforgettable customer service. And I can go on and on and on about the grilled cheese, it was marvelous. Oozing with three different kinds of cheese, fontina, swiss, and brie, the grilled cheese does not stop there. They stuff it with caramelized onions and roasted pears, between slices of gorgeous white bread. And if you are a “Beat Bobby Flay” fan, get yourself the famous fish and chips that beat his version. 

Geja - For a meal that’s both delicious and a romantic experience, Geja’s is a must-try. Their classic menu offers three-course, of a variety of different fondues. Cheese fondue for the first course with bread and fruit for dipping. A bubbling pot of oil for your main course, allowing you to cook the protein and veggies of your choice right at the table. Known as one of Chicago’s most romantic restaurants, Geja boasts over 16,000 engagements over the years!

Do-Rite Donuts and Fried Chicken - Do breakfast right and grab a fried chicken sandwich on a sweet sticky donut and savor the weirdness. I love fried chicken and am quite picky about it, and Do-Rite is high on my list of “fast food” favorites. If the savory-sweet combo isn’t your cup of tea, you can still get a more traditional chicken sandwich. If you go that route, you’ll want to finish your meal with a maple bacon donut. 


The Kit Kat Lounge & Supper Club in Chicago


What to Do

Be Nude Candle Co - Candle making and cocktails with you sweetie(s), anyone? What started as a candle-making business based in Natasha Ellis’ apartment resulted in the recently launched studio with a candle-making class that’s just as romantic as it sounds. In the 90 minutes class, you pick your scent, color, and vessel for the soy wax to be poured into. You’re left with a custom, one-of-a-kind candle to burn at home.

Kit Kat Lounge - What could possibly make a drag show better than it already is? I propose dinner, with tableside drag at the Kit Kat Lounge (pictured above).  Known for a lengthy cocktail menu, Kit Kat Lounge is a by reservation-only drag restaurant, serving dinner all week, and brunch on weekends. 

Ancient Thermal Bath Experience - I’d argue that heaven is a version of the bliss that is found at the Ancient Thermal Baths. Inspired by ancient Roman and Greek bathhouses, the decor and ambition have a luxurious yet mysterious feel. Once you’ve changed and put on your aqua booties, you’ll head down a long staircase to the main event. Half a dozen (or more, I lost count after 6) pools in a variety of temperatures ranging from satisfyingly hot to icey cold laid out in front of you under the dim candlelight. The base experience is 90 minutes long, which is plenty! And put your phone away, it’s not allowed in the baths, which really allows you to unwind and take in the experience.

Chicago Magic Lounge - When you think of dinner and a show, you’re probably thinking of a play or perhaps a classical concert. At the Chicago Magic Lounge, dinner and a show take on a new meaning with tableside magic tricks before the main act, in traditionally Chicago-style magic. The lounge serves drinks and small bites, so if you prefer a more substantial dinner, eat at one of the incredible Chicago restaurants, and then head over to watch the magic while sipping on a drink.


Chaya Milchtein is an automotive educator and journalist who writes about cars, travel, plus size fashion, and queer life and love. Her writing can be found in Real Simple, Fodor’s, and Salon. (@mechanicshopfemme)

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Chaya Milchtein