Best First Date Ideas in Chicago
Best Date Night Restaurants in Chicago
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(Wicker Park)
Discover a Wicker Park treasure that combines gourmet cuisine with an incredibly unique floral service. Opt for a pre-arranged bouquet or create your own at the table to impress your date, all while savoring contemporary American dishes and eye-catching cocktails.
Maple & Ash
(Gold Coast)
Immerse yourself in the opulence of this towering steakhouse, where luxury and celebration meet. Offering an unparalleled dining experience with its exquisite selections and refined ambiance, Maple & Ash sets the scene with plush velvet seating and gorgeous candelabras, ideal for any significant event.
Sepia
(West Loop)
Sepia, boasting a MICHELIN star, shines as both an acclaimed dining spot and a neighborhood treasure. The restaurant’s design reflects its rich history as an 1800s print shop, blending vintage charm with contemporary style. Its carefully curated menu is designed to enchant without pretension, ensuring a memorable experience for any special occasion.
Gibsons Italia
(North River)
Gibsons Italia is celebrated not just for its opulent dishes but for its breathtaking vistas. Perched above the Chicago River and surrounded by towering skyscrapers, this modern Italian-inspired steakhouse provides the perfect backdrop for the most incredible dinner.
Bar Mar
(North River)
José Andrés’s seafood spot is perfect for group dates, with its stunning tapas and unique interiors, highlighted by an octopus sculpture. Must-try oysters, ceviche, and hamachi cones at Bar Mar promise a dining experience reminiscent of a coastal getaway.
Peanut Park Trattoria
(Little Italy)
Created by the minds behind Coalfire Pizza and Tempesta Market, Peanut Park features a warm, rustic vibe. Its acclaimed small menu, featuring standout pasta, pizzas, and seafood, was highlighted by The Chicago Tribune, making it the perfect choice for repeat date nights.
Best Date Ideas for Every Season in Chicago
Spring
Stroll Through Lurie Garden
Experience the magic of Lurie Garden, a captivating 5-acre sanctuary brimming with the beauty of spring, perfect for a date. Take a leisurely stroll hand in hand through this floral wonderland or enjoy a lovely picnic for two, where the vibrant blooms and tranquil surroundings create the perfect Spring backdrop for love to blossom.
Summer
Film or Concert Series
Escape into a world of cinematic charm and musical delight at Millennium Park’s Summer Film or Concert Series. From captivating movie screenings to electrifying live performances, the park transforms into a cultural oasis during the summer months, offering unforgettable experiences for all who gather to revel in the magic of outdoor entertainment.
Fall
Visit The Bean
Many will say they hate it, but fall offers a new perspective on Millennium Park’s unique landmark, Cloud Gate, AKA The Bean. As the leaves begin to turn, this iconic sculpture takes on new beauty, reflecting the vibrant colors of the season while offering the perfect opportunity for a photo-op before grabbing coffee or a bite to eat at Momentum Coffee nearby.
Winter
Ice Skating
While Millennium Park is famed for summer concerts and lush botanicals, winter transforms it into a haven for ice skating. Glide hand in hand at the McCormick Tribune Ice Rink, open from mid-November to March. Afterwards, finish your perfect winter date by treating yourselves to some highly-recommended hot cocoa to warm up.
Best Unexpected Date Ideas in Chicago
