Let Love Rule: Romantic Things to do in Chicago

Chicago is a city full of possibilities and that goes for romance, too. 

If the weather is not completely Arctic, nothing beats a scenic stroll hand-in-hand along the city's beautiful lakefront path with the skyline behind you and future just ahead. Afterward, get close in an alcove at the one-of-a-kind The Darling. Or soar above the city day or night on the Navy Pier Centennial Wheel.

The city is rife with new attractions beckoning couples: The Gwen's Curling Cabin and Rink encourage you to try a sport together and sip hot toddies. Housed in a restored 1902 factory, Aire Ancient Baths  Chicago offers a multi-sensory journey via ancient Roman, Greek and Ottoman bath experiences - leave the cell phone behind. Live jazz fans will appreciate Le Piano, a listening room featuring intimate performances every evening; delicious bites and bubbles. See the impossibly gorgeous skyline on The Odyssey Chicago River  cruise or discover your partner's taste in music at Dorian's, a record shop/60's inspired music lounge hybrid, with sharable tiki cocktails and bar snacks - a happy-go-lucky choice for a romantic night. 


Music and romance are lifelong partners. That's why Dorian's, a new Chicago record shop/60's inspired music lounge hybrid, with sharable tiki cocktails and Asian inspired bar snacks, is a brilliant choice for a romantic night. Michelin starred chef Brian Fisher and John Hess (Beverage Director, previously of Aviary) promise globally inspired cuisine and creative cocktails in the lounge: try short rib banh mi; chicken bao; mushroom won tons; caviar; charcuterie and cheese. Order a house cocktail like Fruity Loops or a sizeable, sharable Cookie Monster (bourbon, coconut, Amaretto and bitters) or a Stormy Daniels may get things rolling. You get to the the intimate setting through the record shop which stocks hand-picked selections from personal collections, online record marketplace, and local partners like Chicago label International Anthem. The record shop features over 600 records equipped with a listening booth with turntables and headphones.

Recommended for Romantic Things to Do because: Couples can break the ice rifling through vinyl in the record shop, then share a big, boozy drink and delicious bites.

Jacky's expert tip: Stop in for happy hour specials, dinner and late night food service, Wednesday through Sundays.

Read more about Dorian's →

Navy Pier Centennial Wheel
Photo courtesy of Navy Pier

The Navy Pier Centennial Wheel is the place for a romantic ride. Located right on Navy Pier, the entertainment venue and biggest tourist attraction in the city. the Wheel offers fantastic views of Chicago's skyline and lakefront. The wheel is 200 feet tall - 50 feet taller than the ferris wheel it replaced. Step into one of the 42 enclosed, temperature-controlled gondolas (or, spend a few more bucks for a VIP gondola with plush seating and glass bottoms) and enjoy the view either day or night. There are also nightly LED light shows from the wheel's spokes and rim. Illinois residents who visit on Mondays between Nov. 1 and March 31 can take advantage of special seasonal pricing.

Recommended for Romantic Things to Do because: It's an unusual way to see Chicago's lakefront and lights, and the view-filled ride can be romantic.

Jacky's expert tip: Weather conditions can sometimes close the Ferris wheel - be sure to check in advance.

Read more about Navy Pier Centennial Wheel →

If you've spent any time in a European city, you know that townsfolk don't park in front of the tv after dinner - they stroll - talking, walking, laughing, getting caught up on the news and hand holding. Since we're Americans, we may feel the need to jog, bike or skate our way along the 18.5-mile lakefront path, but it's beautiful and a lovely way to kindle romance. Expect congestion in the downtown area on summer weekends but it offers unmatched views any time of the year. With the Chicago skyline on one side and Lake Michigan on the other, you'll spy some famous landmarks, including Buckingham Fountain, Navy Pier, Soldier Field, Lincoln Park Zoo and the Adler Planetarium. The gardens and park south of the city, near Northerly Island, add more pastoral elements and dog lovers will want to stop by the beach near Irving Park Road.

Recommended for Romantic Things to Do because: It's Chicago's beautiful backdrop, it's free and can be a casual, unpretentious date.

Jacky's expert tip: For a great skyline view, sit on the rocks at North Avenue, or at a small peninsula between Belmont and Irving Park Road.

Read more about Chicago Lakefront Trail →

Magnificent Mile

Your first inclination may be that a trendy novelty experience might not be exactly "romantic," however, the Dangerous Date package at SafeHouse Chicago could make you as attractive as Daniel Craig or Eva Green. Rather than a goofy contest, this is a serious mission of love, giving couples a night out 007-style. It launches with round trip transportation in an Aston Martin, no less, then the couple covertly enters an unmarked red door at SafeHouse's headquarters. After passing a clearance test, the duo is presented with a bottle of Dom Perignon and a personal tour of the facility with spy-themed souvenirs, A specially catered four-course dinner with cocktail pairings ensues in the private Cone of Silence. Those interested in the Dangerous Date experience, must call a private hotline to book it: (414) 905-1287.

Recommended for Romantic Things to Do because: If you're James Bond fans, the kitschy date can be a memorable beginning of a new coupling or a special anniversary experience.

Jacky's expert tip: The Dangerous Date package is available year round upon request.

Read more about Safehouse Chicago →

There's a new a vessel floating down the Chicago River adding elegance and spectacular views to a romantic journey. The Odyssey Chicago River, the newest addition to the Entertainment Cruises fleet, began cruising in fall 2018 with a design that includes a glass-enclosed structure so you can get 360-degree views of Chicago's architectural show. The cruise offers upscale dining and entertainment, including a dance floor and on-deck musical performances, giving affectionate sailors a serene escape in the heart of the urban landscape. The menu includes luscious options such as a Seafood Tower with Maine lobster, Alaskan King crab and jumbo shrimp; forest mushroom ravioli; braised beef short rib; warm butter cake; and Eli's Original Cheesecake. Choose among award-winning wines, craft beer and specialty cocktails. There are year-round cruising options no matter the weather.

Recommended for Romantic Things to Do because: Architectural cruises are great but when you want to appeal to all the senses, cruising on this sleek all-glass vessel makes a memorable date.

Jacky's expert tip: Dinner cruises follow the longest route, however, there are also lunch, brunch and cocktail cruises.

Read more about Odyssey Chicago River →


Even the name - Ravenswood - sounds like something out of a dreamy English novel and the Chicago neighborhood makes a fine setting for a day and night of love. Take a cocktail class at KOVAL Distillery, Chicago's first distillery and sample organic whiskey, liqueurs and specialty spirits. Entertain your creative spirits at Chicago Glass Collective blowing glass, constructing a coaster or many other projects. It's BYOB, too! Take a dance lesson at Ballroom Dance Chicago (after all, you might need it for the first dance at your future nuptials). The much lauded Band of Bohemia is perfect for a sophisticated dinner with amber lighting that makes everyone look great; or for some of the best Neapolitan pizza in Chicago, head to Spacca Napoli. In summer, saunter through the Montrose Metra Community Gardens. Book a couples massage and lovely room or suite at The Guesthouse Hotel.

Recommended for Romantic Things to Do because: Ravenswood, a destination neighborhood, retains old Chicago charm and is vibrant with a Bohemian bent.

Jacky's expert tip: Craft beer fans should stop in Dovetail Brewery or Spiteful Brewing and who doesn't love the biscuits and sweets at Bang Bang Pie Shop.

Read more about Ravenswood →

Rogers Park

Inspired by the Latin Quarter in Paris, Le Piano's interior design, including massive French windows overlooking an East Rogers Park cobblestone street, dimly lit hushed ambience and deep wine/ Champagne list set the mood. Chicago's expert pianists fill the space with aural love on the centerpiece grand piano. Solo artists take the stage Monday–Thursday from 6 to 10pm; there's a trio playing weekends until 11pm; and various combos entertain on Sundays. Le Piano charges a Salaire d'Artiste (aka a cover charge) which is $5/person added to the final bill. In addition to tables for two, seating options include"Booth 1" accommodating up to 14, a more intimate Sinatra booth, the chaise or a century old wagon that seats a communal dozen. The menu includes French inspired appetizers, small plates, and one bite desserts. Small plates could be crostini with various spreads, sherry laced mushrooms, New Zealand lamb chops and French style chicken thighs.

Read more about Le Piano →

The Gwen's winter terrace is a sweet place to snuggle, try curling, nosh, sip warm adult bevvies and snuggle some more. The wood-paneled Curling Cabin is on the fifth-floor of the property complete with an outdoor porch, Adirondack chairs and a swing seat for two. Inside, choose a table or lounge in the living room area that sports a fireplace and faux furs to drape upon your chill. The iceless Curling Rink gives couples a chance to try their hands at the . curious winter sport in which players slide stones on a sheet of ice towards a target. Admission for The Gwen Curling Rink is $25 per person, which includes a choice of one cocktail and 30 minutes of curling play time. Even if you don't curl, enjoy an Alpine-inspired menu and winter cocktails: fondue; Paulina Market bratwurst; French fries topped with duck confit, duck egg, duck fat gravy, goose pâté, white cheddar; Belgian waffles with Nutella; and mini Churros with maple syrup. There are large-format hot cocktails like mulled wine and hot buttered rum, too.

Read more about The Gwen's Curling Cabin and Rink →

Fulton Market

The Darling is a kitchen and bar, speakeasy-style lounge and a gathering space for dancing the night away. The elegant hideaway is disguised as a flower shop (an homage to the neighborhood's flower markets of old) but hidden behind burgundy velvet-draped windows as seen from the street on Restaurant Row, is a night full of surprises. There's European-focused food, classic and creative cocktails, expert service, whimsical decor oddities and and periodic, novel performances throughout the evening. The Library (downstairs) is ideal for date night with an intimate, quiet and romantic atmosphere; hundreds of vintage books; antique paintings; Persian rugs; and nooks to nibble small plates and sip cocktails. You won't be the first one to think "Downton Abbey" gazing upon the English manor style furnishings. Upstairs in The Ballroom, it's all about spinning chandeliers, celebrating, dancing and socializing with a lively crowd.

Read more about The Darling →

Housed in a restored factory circa 1902 in River West, Aire Ancient Baths Chicago offers a multi-sensory journey via ancient Roman, Greek and Ottoman bath experiences. The signature bath experience includes six thermal baths including hot bath, ice and cold plunges, a warm pool, salt water flotarium and a jet pool. The hot and cold plunges boost circulation, promote flexibility, may enhance immunity and provide a nice endorphin rush. Kind of like love. The Red Wine Bath Experience for Two submerges you two love birds in antioxidant and polyphenol rich Spanish red grapes followed by an hour-long massage with grapeseed oil. If it's possible to chill any more, get to the relaxation area to loll on warm marble stone and sip a selection of teas.

Recommended for Romantic Things to Do because: There are spas galore in Chicago, but AIRE provides a physical and mental melt you can only get in Turkish hamam or ancient Rome.

Jacky's expert tip: Here's your chance to Be Present so leave the cellphone, chatter and ideas of Instagramming this sensual, relaxing experience behind.

Read more about AIRE Ancient Baths Chicago →


Meet Jacky Runice

Born in Bucktown when bulletproof was a home safety choice and not a coffee order, Jacky Runice has been knocking around Chicago as a professional print, online and broadcast journalist and...  More About Jacky