Planning your Valentine’s Day in Chicago with your special someone and unsure what to do? There are endless options to celebrate the holiday with the one you love in the big Windy City.
Whether you’re searching for romantic, intimate date ideas or want to try something new as a couple, explore our top Valentine’s Day activities and attractions her
Valentine’s Day in Chicago: 10 Date Ideas to Celebrate Your Loved One In the Windy City
Below are the 10 top things to do in Chicago for couples on Valentine’s Day, with public transit directions.
1. Enjoy a Romantic Rooftop Dinner at Offshore Rooftop
Source: Offshore Rooftop
Having a Valentine’s Day dinner in Chicago is always a classic option. Take it to new heights at a rooftop restaurant—but don’t worry, you can still keep warm in the city during this time of year.
Offshore Rooftop has the largest rooftop bar in the world, with seasonal glass snow globe seating from late November through February. Have a delicious meal inside an intimate, clear dome with panoramic views of Lake Michigan and the Chicago skyline on a 20,000 square-foot terrace. They also have indoor seating with floor-to-ceiling windows if you prefer.
Offshore Rooftop is located at the end of Navy Pier at 1000 E Grand Ave in the Streeterville neighborhood. You can take the Millennium Metra station, which is a 20-minute walk via the ME and SSL Lines, or you can transfer to CTA Bus #124 for a direct entrance.
2. Have a Luxurious Staycation at the Four Seasons Hotel Chicago
Source: Four Seasons Chicago
Whether you’re a local, travelling from the Chicago suburbs, or parents who want to spend more quality time together, the city can be the perfect staycation for Valentine’s Day at a luxury hotel. At Four Seasons Hotel Chicago, they offer upscale hospitality with cityscape or lakefront suites, a fine dining restaurant, and private architectural tours on a yacht.
They even offer special Valentine’s Day experiences, including:
•Private night spa with champagne, couples’ massages alongside a waterfall-edge indoor pool with exclusive access, and a bouquet of roses
•Martini cart services, where craft cocktails are delivered to your suite with add-on caviar and small bites
•Special menu options from Adorn Bar & Restaurant, featuring lobster gnocchi, wagyu beef tenderloin, live music, and custom-engraved wine glasses
The Four Seasons Hotel Chicago is located at 900 N Michigan Shops. The Chicago train station is an eight-minute walk via the Red Line. The State & Delaware bus stop is a four-minute walk via Bus 36.
3. Embrace Chicago Winter With Couples Ice Skating at Maggie Daley Park
Source: Time Out
Looking for fun things to do in Chicago for couples? Bring out your inner child with your loved one at Maggie Daley Park’s ice skating ribbon. Unlike traditional rinks, it’s an immersive outdoor experience with ice-covered paths that circle the city’s skyscrapers and themed play spaces that come alive even more at night.
Maggie Daley Park is located at 337 E Randolph St, right next to Millennium Park. You can take the Millennium train station, which is a 10-minute walk via the ME and SSL lines. The Randolph & Field Blvd bus stop is less than a five-minute walk via Bus 60.
4. See Exotic Flowers & Plants at the Garfield Park Conservatory
Source: Enjoy Illinois
If you prefer to stay inside during the cold season, you’re sure to impress your date at the Garfield Park Conservatory. It’s one of the largest botanical conservatories in the country, where you can see thousands of exotic flowers and plant species in a panoramic glass canopy. They even offer a spring flower show and a honey extraction workshop on Valentine’s Day.
The Garfield Park Conservatory is located at 300 N Central Park Ave. The Conservatory-Central Park Drive train station is conveniently on-site via the Green Line.
5. Grab a Drink at Winter’s Jazz Club
Source: Winter’s Jazz Club
Searching for hidden romantic spots in Chicago? Take your loved one out on the town at the Winter’s Jazz Club. It’s perfectly tucked away, offering a high-quality and elegant live music experience from top jazz artists. The venue mainly has seating for two for an intimate setting with a full bar and non-alcoholic beverages available.
Winter’s Jazz Club is located at 465 N McClurg Ct, three blocks away from Navy Pier. The Grand train station is a 15-minute walk via the Red Line. The Illinois bus stop is across the street via Buses 2, 29, 65, 66, and 124.
6. Unwind Together at AIRE Ancient Baths Chicago
Source: AIRE Ancient Baths
Rather have more relaxing couples’ activities in Chicago for Valentine’s Day? Unwind together at the upscale AIRE Ancient Baths Chicago. Converted from a factory into a peaceful oasis, they offer thermal baths and spa treatments in a unique setting. It has original exposed brick walls, wooden beams, and dim candlelit rooms with orange blossom fragrances.
There are also special experiences offered for the holiday. These include private couple indoor or outdoor warm bath sessions at different temperatures, a salt exfoliation area, and a steam room.
AIRE Ancient Baths Chicago is located at 800 W Superior St. The Grant train station is a seven-minute walk via the CTA Blue Line. The Milwaukee & Carpenter bus stop is also a seven-minute walk via Buses 8, 56, and 66.
7. Soak in Stunning Art Exhibits at the Art Institute of Chicago
Source: Art Institute of Chicago
The Art Institute of Chicago is a beautiful way to celebrate Valentine’s Day in Chicago for art lovers. They have love-themed exhibits, self-guided tours, and free weekday entry for Illinois residents from early January to late February. With thousands of artworks and collections from around the world, it’s also a great way to stay warm inside during this season.
The Art Institute of Chicago is located at 111 South Michigan Ave. The Adams/Wabash train station is across the street on all train routes. The State & Adams bus stop is a five-minute walk via Buses 2, 29, 146, 147, and 148.
8. Take a Couple’s Ballroom Dance Class at Duet Dance Studio Chicago
Source: Duet Dance Studio
Want a creative way to better bond with your loved one? Get out of your comfort zone with ballroom dance classes at the award-winning Duet Dance Studio Chicago. They also have a Valentine’s Day dance class where you can learn a simplified version of the Dirty Dancing routine, basic salsa steps, and couples’ leading/following choreography—which sells out every year!
Duet Dance Studio Chicago is located at 2412 W North Ave. The Western train station is a 10-minute walk via the CTA Blue Line. The North Ave & Western bus stop is across the street via Bus 72.
9. Go on a Valentine’s Day Dinner Cruise
Source: City Cruises
One of the most romantic things to do in Chicago is a Valentine’s Day dinner cruise. It’s a unique dining experience on a luxury glass-enclosed vessel along the Chicago River for 2.5 hours. Hosted by City Cruises, it includes a three-course meal, specialty cocktails, live music, and a climate-controlled open-air deck so you can stay warm while taking in panoramic cityscape and waterfront views. There’s also a fireworks display that you can see up close from the Navy Pier for exclusive, special memories with your loved one.
City Cruises is located at 455 N. Cityfront Plaza Dr on Navy Pier. The Grand train station is a nine-minute walk via the Red Line. The Columbus & Illinois bus stop is a two-minute walk via Buses 66 and 124.
10. Have a Sweet Treat at Local Bakeries
Source: Magnolia Bakery
End your perfect Valentine’s Day in Chicago with a sweet treat at local bakeries. The Windy City has so many options with diverse cuisines to choose from.
Some of the most highly-rated bakeries in Chicago are:
•Magnolia Bakery Chicago: Known for its red velvet cupcakes, with popular menu items such as Valentine’s Day cakes and fresh banana pudding. They’re located at 108 N State St in the Loop neighborhood.
•Jennivees Bakery & Cafe: A local bakeshop featuring oversized cake slices, unique flavored cupcakes, and breakfast pastries. They’re located at 2925 N Halsted St in the Lakeview neighborhood.
•Weber’s Bakery: A long-running local bakery since 1930, offering signature cookies, cakes, and homemade breads. They’re located at 7055 W Archer Ave in the Southwest Side neighborhood.
Find Your New Home Sweet Apartment Home in Chicago With Your Loved One
Are you looking for a new apartment with your significant other? At TLC Management Co., we have over 30 properties in the Chicagoland area with the local expertise to find you the best place to live together.
We have unique and convenient amenities for various lifestyles, including:
•Lakefront communities with private beach access and sun terrace
•Walk-in closets with organizer shelving and oversized windows in renovated units
•Resident-exclusive Bark Park with tree-lined trails
Ready to start your search?
Check out our city and suburban properties or contact us at info@chicagorentals.com to schedule a tour today!
