Most Romantic Things to Do in Chicago

Let love rule: romantic things to do in Chicago

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

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. The Forest Preserves of Cook County is waiting with birding and fishing; sledding hills; and miles of trails for exercise and nature hikes to spy native plants and animals, from otters to oaks to orchids. Who says love has to have a price tag? Get into a fun, environmentally friendly, inexpensive sport at the Morton Arboretum - snowshoeing or cross country skiing allows time together in the crisp outdoors.

The Joffrey Ballet, one of the premier dance companies in the world, offers a sensual experience of mystery and artistry or follow the conga line to Carnivale Chicago for a 1950's style show inspired by the original Copacabana Club in New York City. 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. Sushi Suite 202, Chicago's only in-suite Omakase experience is the definition of intimate. Why not stay overnight in the boutique Hotel Lincoln enjoying rooftop sips and next-day brunch?

The Chicago run of Frida: Immersive Dream promises to be a new way of experiencing Kahlo's art, surrounding viewers with the brilliant work of one of the most beloved artists of the 20th century. 


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. For Valentine's Day, two new limited edition experiences are available only from Feb 11-14, 2022 so book soon. Other days, there are couples' treatments like the Wine Bath Experience for Two which submerges you in antioxidant-rich Spanish red grapes followed by an hour-long massage with grape seed 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 idea of Instagramming this sensual, relaxing experience behind.

Read more about AIRE Ancient Baths Chicago →

Whether your shared approach to food is more thoughtful, adventurous Bourdain or chirpy Rachael Ray, get closer to fine at one of the great couples' classes at Chicago's The Chopping Block. Valentine's Day classes include Mediterranean Feast; Demonstration Brunch; An Evening in Italy; andVirtual Breakfast in Bed but if those are full, check out regularly scheduled Date Night classes. There's Hands-On Date Night: Warming Winter Dinner Party or Coqs and Corks: Fried Chicken and Wine Pairing at the Merchandise Mart: location. How about Chocolate Boot Camp or Hands-On Macaron Workshop, both taking place in Lincoln Square. Perhaps you two love birds are peckish about so much meat in your diet. Sign up for Vegetarian Boot Camp, an immersion into vegetarian cooking using ingredients from different cuisines as well as vegetarian proteins.

Recommended for Romantic Things to Do because: If "cooking is love made visible," why not get better at it - together?

Jacky's expert tip: Choose Lincoln Square or the Merchandise Mart. Valentine's classes fill quickly but there are numerous couples' classes throughout the year.

Read more about The Chopping Block →

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.

Read more about Chicago Lakefront Trail →


Fairmont Lodge, at the sophisticated, modern Fairmont Chicago, celebrates winter in a romantic way with cozy d├ęcor, indoor "fire pits," and overnight packages. The Fairmont Chicago Lodge is in its inaugural winter season nestled between Millennium Park and the Magnificent Mile so you can shop, stroll or ice skate then visit the attraction. It's a toasty haven for couples to relax and get snuggly with the newly introduced indoor Fire Pits. Choose among three different food and beverage packages including: The Spark: $25 for up to four guests that includes dessert s'mores; The Campfire: $50 for up to four people which includes cheese charcuterie, Champagne toast and dessert s'mores; and The Hearth, $75 for up to four guests for sweet or savory fondue, four cocktails or mocktails and dessert s'mores. The Fire Pits are available to book every Wednesday through Sunday from 4p.m - 11p.m. Each of the nine fire pits can accommodate up to eight people.

Recommended for Romantic Things to Do because: Overlooking Lake Michigan, Grant and Millennium Parks and with skyline views, Fairmont Chicago adds a cozy, romantic opportunity to enjoy a winter lodge experience.

Jacky's expert tip: Reservations are required for the evening lodge experience - book online.

Read more about Fairmont Lodge →

Cross country skiing and snowshoeing are not only affordable in this neck of the snowy woods, they are stellar calorie scorchers; a hushed activity you can either learn together or practice; and both help reduce stress (and who doesn't need that this year)? The ski and snowshoe rental season here runs from Jan. 15 to March 21, 2022, when there are four or more inches of snow. Supplies are limited due to equipment shortages, and available on a first-come, first-served basis or bring your own cross-country skis or snowshoes when there are four or more inches of snow. Cross-country skis (includes boots and poles) rent for $20, snowshoes for $15 ($13 children ages 10 and younger. The Arboretum boasts 1,700 acres on the rolling Valparaiso moraine. Try snow shoeing - the only qualification is the ability to walk so there's no learning curve, just outdoor quiet time with your partner.

Recommended for Romantic Things to Do because: Enjoy fresh air, quiet time with your partner, a low impact but significant workout and charge some endorphins.

Jacky's expert tip: Celebrate Valentine's Day weekend with a prix-fixe (adults-only) dinner, with wine pairings and live music, overlooking beautiful Meadow Lake.

Read more about Morton Arboretum →


Ballet showcases the miraculous art of the human body and a night at the ballet, especially one featuring the accomplished Joffrey company, can be most romantic indeed. The Joffrey Ballet kicks off 2022 with a fresh interpretation of Don Quixote presented during the Joffrey's first-ever season at the historic Lyric Opera House. Don Quixote features a feisty heroine who is in love with one man but her father promises her to another. She devises a plan to marry her true love and pursue her own happiness. All characters, including Don Quixote and Sancho Panza, are inspired by "the romance of the night." Expect a feast for the senses with multi-media projections, puppetry and live music performed by the Lyric Opera Orchestra. Even better, it's an affordable date - tickets start at $35. Check the website for upcoming performances throughout the year including the premiere of Serenade by dance pioneer George Balanchine.

Recommended for Romantic Things to Do because: Joffrey is one of the premier dance companies in the world, and a night at the ballet is a sensual experience of mystery and artistry.

Jacky's expert tip: Newly renovated, The Florian restaurant on Lyric's third floor offers a three-course prix fixe menu with a supper club ambience.

Read more about Joffrey Ballet of Chicago →

Who says a romantic outing has to put you in debt? Forest Preserves District of Cook County offers year-round and seasonal activities for couples, most for free. Stargaze year-round: in 2021, the International Dark-Sky Association designated the Palos Preserves in southwest Cook County as the largest Urban Night Sky Place in the world. You can see four times more stars there than in the city. Consider Moonlit walks for couples starting from Little Red Schoolhouse Nature Center in Willow Springs. Stroll through the preserves year-round - there are over 350 miles of paved and unpaved trails from which to choose like the Des Plaines River Trail. When there's snow on the ground, check out snowshoes for free from the River Trail Nature Center in Northbrook. Take photos along the way and submit them to the Friends Photo Contest, hosted by Friends of the Forest Preserves. Mark your calendar for the 6th Annual Beer in the Woods at LaBagh Woods in Chicago (September 24, 2022). Sip among 40 microbrews and enjoy nature walks, crafts, live animals, music, and food trucks.

Recommended for Romantic Things to Do because: It's romance on a budget with camping, birding and fishing; sledding hills; miles of trails to see native plants and animals, from otters to orchids.

Jacky's expert tip: The forest preserves are closed at night, but are open for special events like the moonlit walks.

Read more about Forest Preserves of Cook County →

Lincoln Park

Book an unparalleled, multi-layered tryst all in one place. Check into your accommodations at the boutique Hotel Lincoln (ask for a lake view room). Then indulge in a 17-course, 75-minute Omakase sushi dining extravaganza in Suite 202. The one-of-a-kind space is a hotel room turned sushi speakeasy that is akin to a living room with velvet furniture, a six-seat cocktail area and a six-set sushi bar. Intimate? You bet. Finish the evening with new "cosmic cocktails" on the glass-enclosed rooftop at The J. Parker that'll make you feel as though you're in a snow globe with views of the lake and skyline. Wake up for coffee at Elaine's then enjoy brunch service at The Kennison. Take a walk around the free-admission Lincoln Park Zoo (just across the street,) or explore the Chicago History Museum, also nearby.

Recommended for Romantic Things to Do because: Chicago's only in-suite omakase experience is the definition of intimate. Coupled with an overnight, drinks and brunch - you've hit the romantic jackpot.

Jacky's expert tip: Book your Sushi Suite experience online at Open Table. Check the hotel's website for special packages - some include breakfast and others may include valet parking.

Read more about Sushi Suite 202 →

If you can't join the conga line to Rio, Carnivale Chicago offers festivities for couples at the "Copa." Samba yourselves silly as an interactive cabaret-style 90-minute dining entertainment experience whisks you to Latin America with music, dance, mixology and cuisine. No matter where your ancestors hail, become Latin lovers during the uplifting performance in the colorful Carnivale dining room. The 1950's style performance inspired by the original Copacabana Club in New York City features world class talent: Brazilian dancers, feathered showgirls, live music from an Afro-Brazilian band and acrobatic aerialists. You'll feel the magic of the legendary Copacabana without having to hop on a plane or a wayback machine. . Tickets are on sale online and include a three-course prix fixe meal crafted by Executive Chef Carlos Lucas Garza. Life is a carnivale!

Recommended for Romantic Things to Do because: The lush interior, vibrant artwork and 1950's inspired Copacabana Club show whisks lovers from chilly Chicago to the heat of Latin America.

Jacky's expert tip: Tickets are $129 per person with performances upcoming on Jan. 27; Feb. 24, March 10, March 24, April 14 and April 28, 2022. Seatings take place 6 pm and 8:30 pm.

Read more about Carnivale Chicago →

The same team that created Immersive Van Gogh aims to thrill again with Frida: Immersive Dream opening in Chicago Feb. 24, 2022. The 20th-century artistic icon's life reads like an adventurous romance novel filled with passion, revolution and heartbreak. Even though her art can be found everywhere, from coffee mugs to tee-shirts, it's her emotional vitality and vibrant colors inspired by her native Mexico that draw admirers from across the planet. The folk art, mysticism, surrealism and magic realism will come to life via projections shown on the venue's massive walls, using state-of-the-art projectors and high-quality sound systems and a score that heighten the experience. The experiential art exhibit runs Feb.24 through May 28, 2022. Ticket prices start at $39.99 with timed and flexible options available.

Recommended for Romantic Things to Do because: It's an opportunity to surround yourselves in the artistic icon's work and passion during this limited run.

Jacky's expert tip: A recent sale of Frida Kahlo's 1949 painting "Diego and I," sold at Sotheby's for $34.9 million dollars and is now the most prized piece of Latin American artwork ever sold at auction.

Read more about Frida: Immersive Dream →


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