Unforgettable Places to Propose on Chicago’s North Shore

Put a ring on it! If you are about to pop the big question to the love of your life, make it a “wow” moment in one of these romantic spots. A celebratory toast with a tasty meal is the perfect follow-up stop for what just might be the sweetest day of your life. Get creative and find more exciting locations when you Explore North Shore Attractions. 

 

Chicago Botanic Garden, Glencoe

Picture-Perfect Great Outdoors
Imagine the most romantic moment ever in one of the most beautiful settings imaginable. Wander or pose throughout Chicago Botanic Garden’s (Glencoe) colorful and fragrant rose gardens, sparkling water features, and darling archways with an abundance of flora to fawn over. They’ve even scoped out some prime spots to pop the question. Grosse Point Lighthouse (Evanston) wins for an iconic landmark site right on the shores of Lake Michigan. Stroll hand-in-hand through Sugar Maple woods filled with birdsong along self-guiding trails by the River Trail Nature Center (Northbrook).
 

Clark Street Beach, Evanston

Beautiful Vistas on the Water 
For a beachy vibe, do your betrothing on one of a half-dozen Evanston Beaches along the lakefront (Evanston). You can pick a pretty place in the parks or on the sand at sunset and include the Chicago skyline for effect. Rent a tandem kayak and set the scene to just you two on the water where maybe a heron will witness the big moment on the Skokie Lagoons (near Winnetka). Ponds and fountains are just some of the charming features at The Grove (Glenview). A stunning 150+ acres of forest, elegantly landscaped gardens and urns filled with seasonal flowers surrounds their 1930s-era Renfield Estate with pavilion and gazebo. 
 

Chevy Chase Country Club, Wheeling

Romance with a Side of Storybook Scenery
For a proposal with historic charm, head to the Charles Gates Dawes House (Evanston). With its stately facade and Lake Michigan backdrop, it’s pure romance—plus house tours are available Thursday–Sunday (1-4pm) if you want to explore before or after. Love on the links? Pop the question at Chevy Chase Country Club (Wheeling), where 18 beautiful holes and sweeping views set a romantic tone. Its scenic greens make a stunning proposal spot—and maybe even your future wedding venue.  

 

The Perfect Spots to Celebrate Saying Yes

 

Guildhall, Glencoe

Celebrate with a Toast and a Taste
With stars in your eyes and an engagement ring ‘round that finger, extend the lovefest into the evening. The warm welcoming atmosphere at Avli Restaurant (Winnetka) compliments their lovely and lively outdoor patio where oenophiles enjoy dozens of wine options at this “Inspired” Greek hotspot. Guildhall Restaurant (Glencoe) commits to all things local and artisanal in their sophisticated American bistro with European flair. If you fancy Happy Hour or unconventional French-Moroccan fare, LeTour Brasserie (Evanston) boasts a beautiful bar and magical outdoor patio. 
 

Libertad, Skokie

Cheers to More Dining Gems
After a day with your darling in gardens, beaches, or attractions, get a table at Morton’s the Steakhouse (Northbrook). Enjoy a flight of wine or spirits to seal the deal with their exceptional service and premium classic fare. Cozy Libertad (Skokie) serves up small-plate flavors from a mosaic of Latin American countries. Toast your new relationship status with their Cava Brut Reserva or Cava Brut Rosé. Taverna Naxos (Wilmette) elevates some truly unique flavors from the Greek Isles. Ask for two forks to share the to-die-for Baklava or Baklava Cheesecake.