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Windy City Romance: 17 Unforgettable Chicago Dates to Woo Your Sweetheart!

Chicago Hotel Collection

17 unforgettable Chicago dates to woo your sweetheart!

Whether you're a long-term Windy City couple or just visiting for a romantic weekend getaway, Chicago offers countless opportunities for lovebirds. From jazz-filled nights to riverside strolls, here are 17 fun date ideas to spark up your romantic life.


But first, a special note to our travelers. Staying with the Chicago Hotel Collection will add a cherry on top of your sweet date. Our exclusive guest amenities package offers savings on various Chicago activities, making your stay all the more delightful. Now, let’s dive into those dates!

  1. Architecture River Cruise: Get a unique perspective on Chicago's skyline with a guided river tour.

  2. Visit Millennium Park: Snap a selfie with "The Bean" and revel in the city's vibrant culture.

  3. Chicago Cultural Center: Marvel at stunning art exhibits and Tiffany-stained glass domes.

  4. Take a Cooking Class Together: Spice up your love life by learning to cook a new dish.

  5. Go to a Jazz or Blues Club: Dance the night away in a historic Chicago music venue.

  6. Explore the Art Institute of Chicago: Appreciate art hand in hand in one of America’s most prestigious museums.

  7. Garfield Park Conservatory: Escape the cold in a tropical paradise right in the heart of Chicago.

  8. Visit Navy Pier: Ride the Ferris wheel and share a cotton candy while overlooking Lake Michigan.

  9. Helicopter Tour: Soar above the city and take romance to new heights with a helicopter ride.

  10. Adler Planetarium: Count the stars and make a wish at this fascinating space museum.

  11. Attend a Chicago Sports Game: Cheer for your favorite Chicago team and make lasting memories.

  12. Hot Chocolate at Mindy’s Bakery: Cuddle up with Chicago's best hot chocolate on a chilly day.

  13. Couples Spa Day: Indulge in a pampering spa treatment to rejuvenate your love.

  14. Rent a Tandem Bike: Explore the Lakefront Trail with a tandem bike for two.

  15. Chicago Symphony Orchestra: Enjoy an elegant night with world-class musical performances.

  16. Private Sunset Sail: Sail into the sunset on Lake Michigan with your special someone.

  17. Explore Neighborhoods: Unearth hidden gems in local neighborhoods and create unique memories.


Make the Most of Your Date with the Chicago Hotel Collection!


Staying with the Chicago Hotel Collection isn’t just about comfortable rooms and fantastic service; it's about experiencing the city like never before. Our exclusive guest amenities package provides access to some of the best experiences in Chicago at a discounted price!


Whether you want to dance to the city's jazz, enjoy a romantic dinner cruise, or explore fascinating museums, we've got you covered. Simply ask our concierge for details, and we'll guide you on how to make the most of our exclusive offers.



Romance in Chicago is as diverse as its skyline, offering something for every type of couple. The city is a playground of culture, arts, and endless fun. By staying with the Chicago Hotel Collection, you'll not only enjoy a comfortable and elegant stay but also have access to exclusive discounts that make these fun dates even more accessible.


So pack your bags, bring your love, and embark on an unforgettable journey through the heart of Chicago. With these 17 ideas in your pocket, you're guaranteed to have a date that's as enchanting as the Windy City itself. After all, Chicago is not just a destination; it's a romantic adventure waiting to be explored!

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