There’s a reason the romantic allure of urban destinations like New York City, Paris, and London endures; cobbled streets of historic neighborhoods are ideal for long walks hand in hand, historic and modern architecture provide elegant backdrops for connecting with your partner in a new locale, and world-class fine dining encourages leisurely dinners of a bygone era. Still, there’s plenty of novel and emerging amorous-centric cities to explore, including our latest crush, Chicago.
We've compiled a guide to showcase what makes Chicago so special for lovebirds, along with a little help from some local Michelin Key hotels’ concierges. Here’s how to plan the most romantic weekend in Chicago.
Friday
Begin your adoring weekend away at Brindille, a “romantic favorite” of Bob Klees, concierge at Pendry Chicago, a Two MICHELIN Key property. Its intimate and sexy style offers an ideal embrace to the city’s culinary scene thanks to Chicago native, co-owner, and executive chef, Carrie Nahabedian. Borrowing the vibes of a Parisian bistro with the flair of favored French dishes, Nahabedian presents a constantly updated menu that pairs seasonal produce with French technique. Continue your first night down the street at The Bamboo Room, a locals' favorite bar-within-a-bar at Three Dots and a Dash. Beverage director Kevin Beary designed the niche space to pay homage to rum and rhum agricoles; with over 300 rums available, the collection is one of the most extensive in the country. Whether or not you’re sipping a rare expression neat or a classic tiki cocktail, a nightcap here induces a honeymoon-esque aura as it transports couples to a beachside bungalow without leaving the heart of Chicago’s River North neighborhood. For another option, there’s Untitled, revered as “Chicago’s premier speakeasy,” according to Judson Corrie, assistant director of guest experiences and concierge services at the Waldorf Astoria Chicago, a One MICHELIN Key hotel. “The vibe is dark and tantalizing,” he says, with an “exhaustive collection of rare whiskey that allows the evening to take on a life of its own.”
Saturday
Couples seeking utmost rest and relaxation may want to opt for breakfast in bed; a true luxury when snuggled between high thread count linens. Of course, if you prefer to make the most of your time in Chicago, you may want to hit the streets early. For a quick bite, grab a bagel, coffee cake, danish, croissant, or a number of other sweet and savory artisanal pastries from Mindy’s Bakery, opened in 2022 as an evolution from longtime and citywide favorite pastry chef Mindy Segal.
Whether or not you’ve been to Chicago before, use the afternoon to explore some of its beloved sights from the 12-foot stainless steel Bean in Millennium Park to the Ferris wheel at Navy Pier. If you’re visiting when the windy city is touting its moniker, you might want to hunker down and observe the city from the inside out. The Willis Tower observatory offers a picture-perfect vista, or if you wish to sip or nibble, try Z Bar atop The Peninsula Chicago, a Two MICHELIN Key hotel. There’s also a 90-minute river cruise that is a popular way to witness Chicago’s new and historic architecture; the evening time slot is perfect for watching the city turn from day to night as the facades light up and their reflections dazzle in the Chicago River.
When it comes time for dinner, you’ve got options: from new American fare to Middle Eastern prix-fixe to sushi and sake. Discover the quality and purity of ingredients at Andrew Zimmerman’s One MICHELIN Star Sepia; organic and sustainable aren’t just buzz words here, they’re the menu’s foundation. The four-course menu rotates throughout the year, but there’s always an option to start with an additional course of golden kaluga caviar — a must for date night. At Middle Eastern restaurant and One MICHELIN Star, Galit, Chef Zachary Engel offers a farm-driven, four-course experience accented by a stellar wine program (a majority of labels are from small producers in Lebanon, Palestine, Israel, and Armenia). Snag a reservation at Galit for something entirely unique, all while wrapped in the unpretentious comfort of brick walls, wooden booths, and an open kitchen.
No matter where you dine, make sure to leave room for a nightcap. Dearly Beloved is a shiny new cocktail bar that emphasizes eccentric ingredients, like snap pea infused gin and insect derived tinctures, to lead your senses on a journey.
Sunday
Wake up slowly over a fire-roasted seafood tower and Alaskan King Crab eggs Benedict during an elegant Sunday brunch at Maple & Ash, a favorite of Klees. If you prefer an even more gradual start to the day, Klees suggests booking a couples experience at AIRE Ancient Baths. “The Love Connection [experience] includes a massage for two, a thermal bath, and fresh juices when you arrive.”
After a proper brunch or morning of pampering, spend an afternoon wandering the exhibits of The Art Institute of Chicago. As the second largest contemporary art museum in the country, there is a collection for every couple to enjoy. Sports-enthused couples may want to catch a game (and a Chicago-style hot dog) at Wrigley Field if the Cubs are at home. Otherwise, simply strolling the 2.7-mile-long 606 rail line turned pedestrian greenway permits plenty of opportunities to observe Chicago from all its beloved angles.
Finish off your trip with a reservation at Trivoli Tavern, advises Corrie. “Follow the tunneled stone walkway down the neatly tucked away alley that leads red antiqued doorway to this old-world American tavern,” teases Corrie. Tuck into a red leather banquet of a candlelit table and browse the menu for a selection of “vintage supper club fare rarely found elsewhere.” The combination of old-world charm and urban elegance present an elevated but not extravagant conclusion for your final night. Corrie suggests taking your time and starting with an expertly made Old Fashioned before diving into hand-cut pasta or a decadent Prime Rib.
Where to stay
“Waldorf Astoria Chicago was meant for lovers,” says Corrie, of this one-Michelin-key property. The rooms are outfitted with secluded balconies and personal in-room fireplaces that he says are an idyllic spot to snuggle up and admire the vista of the Gold Coast neighborhood. The common areas evoke a residential feel that’s elevated by Parisian mansard roofs and a cobblestone courtyard; there’s an ultra-luxurious spa, velour-clad speakeasy cocktail bar and a fine-dining all-American restaurant complete with leatherbound booths and dainty fresh flowers atop each table. For couples seeking something extra special, Corrie says, “Add on a custom rose petal turndown service, select from an expertly curated vintage wine menu and toss a coin in our fountain for lucky and lovely years to come.”
With two Michelin Keys, Pendry Chicago promises pristine luxury in its noble abode — the former 1929 Carbide and Carbonic Building that’s a stunning preserved symbol of Art Deco architecture. The property features more than 300 guest rooms, 81 one of them suites, as well as a French brasserie, oyster and Champagne bar, and the Pendry’s quintessential bar — an opulent, moody lounge that beckons you to gather around the fireplace to both start and finish your night in style. Pendry Chicago also boasts a 24th floor rooftop which is ideal for enjoying Chicago at a more leisurely place. When it comes time to venture throughout the city, the hotel’s address on Michigan Avenue places you within walking distance to some of Chicago’s most popular attractions, from Magnificent Mile to Millennium Park and the city’s theater district.
Another two-key property, The Peninsula Chicago’s been a mainstay of the city’s skyline and accommodations since it opened in 2001. The Hong Kong-based brand brought with it Asian grandiosity from its soaring lobby to its buttoned-up bell boys and lavish rooms clad with marble, velvet and gold. The sexy and luxurious design of its guest rooms extend into its four dining concepts that satiate a variety of culinary cravings from morning until late night. The spa’s sun terrace (outfitted with a hot tub) and pool makes for a cosseted way to spend an afternoon (after a couples’ massage of course) overlooking Chicago’s skyline with bubbles in hand.
Address Book:
The Bamboo Room at Three Dots and a Dash
435 N Clark St, Chicago, IL 60654
Untitled Supper Club
111 W Kinzie St, Chicago, IL 60654
Mindy’s Bakery
1623 N Milwaukee Ave, Chicago, IL 60647
Little Goat Diner
3325 N Southport Ave, Chicago, IL 60657
The Omakase Room
63 W Grand Ave, Chicago, IL 60654
Dearly Beloved
900 N Franklin St, Chicago, IL 60610
Trivoli Tavern
114 N Green St, Chicago, IL 60607
Hero image: Max Bender on Unsplash
