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 the 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. Explore Ravenswood together, a Chicago neighborhood that makes a fine setting for a day and night of love. For a romantic getaway in the heart of the city, Hotel Julian offers the Cultured and Cuffed package inspired by Chicago's famous couples.

The city is rife with new attractions beckoning couples: The Gwen's Curling Cabin and Rink encourages you to try a sport together and sip hot toddies. Come by in summer when the experience transforms into a glamping tent. 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. Cast a spell at The Magic Parlour 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 light, romantic night. Michelin starred chef Brian Fisher promises globally inspired cuisine and creative cocktails in the lounge: try short rib banh mi; chicken bao; mushroom won tons; or charcuterie and cheese. Order a house cocktail like Four Lovers or the I Don't Want No Shrubs; or a sizeable, sharable Spicoli (Plantation Three Stars Rum, Jager, Coconut Thai Banana, Vanilla, Pineapple) may get things rolling for the fast times. You get to 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.

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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 (and it's quiet up there)! 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.

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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, 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 near Northerly Island add more pastoral elements and dog lovers will want to stop by the beach near Irving Park Road. Who says love has to have a price tag?

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.

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Hotel Julian's Cultured and Cuffed package is inspired by Chicago's famous couples. The Barack and Michelle Obama package is a date at The Art Institute (where Chicago's renowned couple had their first date in 1989). Stroll through the fine Impressionist works or the Modern Wing, then it's a 10-minute walk back to Hotel Julian for an in-room champagne toast. Melissa McCarthy and Ben Falcone met in a comedy writing class here in 1998. Choose the McCarthy and Falcone romance package and receive tickets to Second City and pre-show cocktails at About Last Knife (ALK), the modern steak bar adjacent to Hotel Julian's lobby. The legendary architect of the Atlantic Bank Building where Hotel Julian now stands, Benjamin Marshall married Elizabeth Walton in 1905. There are two exclusive experiences inspired by the couple including an Architecture Center package and another with VIP access and private tour at the Chicago Cultural Center.

Recommended for Romantic Things to Do because: For a romantic getaway in the heart of the city, Hotel Julian offers the Cultured and Cuffed package inspired by Chicago's famous couples.

Jacky's expert tip: When booking, request one of Hotel Julian's contemporary, well-appointed rooms with picturesque cityscape and Millennium Park views.

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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. Playful daters should visit Redline VR, a virtual reality (VR) arcade bar. 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 will go for Dovetail Brewery or Spiteful Brewing and who doesn't love the biscuits and sweets at Bang Bang Pie Shop.

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The Gwen's winter terrace is a sweet place to snuggle, try curling, nosh, sip warm adult bevvies and cozy up by the fireplace. 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 playtime. Even if you don't curl, enjoy an Alpine-inspired menu and winter cocktails including large-format hot cocktails like mulled wine and hot buttered rum.

Recommended for Romantic Things to Do because: Sparkling lights and wintry tunes set the scene for a romantic ski chalet experience.

Jacky's expert tip: The Gwen's outdoor terrace, Curling Cabin and Curling Rink are open daily from 11 a.m. to 11 p.m. In the warmer months, book the luxe glamping tent.

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Enter the diminutive ballroom tucked inside the historic Palmer House Hilton Hotel and get ready for The Magic Parlour starring Dennis Watkins. You're escorted from the grand Palmer House lobby through the hotel to a private showroom. Pick your glass of wine and sit cabaret-style with only 44 seats ensuring plenty of interactive magic and mind-reading. Chicago's longest-running magic show is a fun night out for couples (cocktail attire is recommended) amid the romantic nostalgia of the Palmer House. It's full of cheeky humor and plenty of how-did-he-do-that moments courtesy of the third-generation magician. Tickets are $79 each and include beer, wine and soft drinks served during the performance.

Recommended for Romantic Things to Do because: Love is all about magic, smoke and mirrors and sleight of hand - right?

Jacky's expert tip: Consider pre-booking a prix-fixe Magic Menu at Lockwood Restaurant & Bar, inside the Palmer House, before or after the show for The Magic Parlour ticket holders for $41 per person, all-inclusive.

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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 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.

Recommended for Romantic Things to Do because: There's nothing else like it in Chicago offering surprising pop-up performances, European bites and cocktails served in antique glassware.

Jacky's expert tip: You'll get the full experience evenings Thursday - Sunday between 7 pm-10 pm when both areas are open. Performances normally begin around 8 pm.

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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 a hot bath, ice and cold plunges, a warm pool, saltwater 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.

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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, and dimly lit ambiance plus a deep wine/ Champagne list set the mood. Solo artists perform Monday, Wednesday and Thursday nights; Tuesdays are Cabaret shows with visiting vocalists; Fridays and Saturdays launch with solo cocktail piano and then jazz quartets entertain until midnight. Sunday brunch is accompanied by jazz trio and evening brings a vocal and piano duo. 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 tartlets with pesto and goat cheese; New Zealand lamb chops; and French chicken thighs.

Recommended for Romantic Things to Do because: Music loving lovers will appreciate the bohemian listening room featuring intimate performances every evening; delicious bites; and bubbles.

Jacky's expert tip: Le Piano charges a Salaire d'Artiste (aka a cover charge) which is $5/person added to the final bill.

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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