Best North Shore Anniversary Ideas: Romantic & Unique Dates for Couples

Are you looking for the best North Shore anniversary date night ideas for couples?

If so, then you’re in the right place! Whether you’re looking for adventure, relaxation or something you can wrap up in a pretty box, I’ve got you covered. This list is for all types of couples - whether you are celebrating your first anniversary, your fifth anniversary or your fiftieth anniversary! You could also be celebrating a dating anniversary, a wedding anniversary, or just need an idea for a fun night out!

Liz Hansen of Chicago Boudoir

I’m Liz and I run the Chicago Boudoir Photography studio. But when I’m not at work, I love exploring Chicago’s North Shore and everything this amazing area has to offer. I’ve lived in the Chicago area since 2012 and currently live just outside of the city in Evanston, IL. I’ve also been married since 2006 and I’m always looking for fun new ways to celebrate our anniversary.

I’ve organized this list based on the month of your anniversary. So scroll to your anniversary month and find a great North Shore option to celebrate!

I’ve tried almost all of these myself, so you can trust my recommendations!

January - Indulge Your Senses at a Spa

Beat the winter chill by indulging in a relaxing spa experience. Enjoy luxurious treatments designed to help you unwind, recharge, and refresh your senses.

Book a room with your own private pool and hot tub (and even a water slide if you want!) and experience a romantic paradise like none other.

King Spa in Niles

Experience this Korean-style spa in Niles that offering many treatments options, including saunas, body scrubs, massages, and herbal steam therapies. The King Spa also features unique relaxation rooms such as the Ice Room and the Salt Room.

February - Discover the Molecular Gastronomy Scene

Take your dining to the next level with a visit to one of the area's top molecular gastronomy restaurants, where culinary creativity transforms food into an unforgettable work of art.

A refined French-American bistro in Winnetka, Aboyer offers an upscale yet approachable dining experience with classic French techniques and modern American flavors.

Le Colonial in Lake Forest

Located in Lake Forest, Le Colonial offers an elegant dining experience with French-Vietnamese cuisine, combining rich, traditional flavors in a colonial-inspired setting.

March - Be Adventurous

Shake off the winter blues with an adrenaline rush! Test your aim with axe throwing or take the ultimate icy plunge into Lake Zurich—if you dare.

Axe throwing in Glenview

Unleash your inner lumberjack at Bullseye Axe Lounge in Glenview, where you can channel your strength and skill into an exhilarating axe-throwing experience!

The Plunge Lake Zurich

The Plunge is an annual charity event where participants jump into the icy waters of Lake Zurich, raising funds to support families affected by cancer.

April - Enjoy Nature

Spring is in the air! Celebrate the season by exploring the North Shore’s stunning outdoor spaces. Take a peaceful stroll through blooming gardens or wander expansive parks—natural beauty is everywhere.

Chicago Botanic Gardens

Discover a stunning array of themed gardens, from serene Japanese gardens to vibrant rose gardens, spread across 385 acres of picturesque landscapes.

Once a historic military base, Fort Sheridan Forest Preserve now features scenic trails, lakefront views, and diverse habitats, blending nature with rich history.

May - Go to a Show

Immerse yourself in the North Shore’s dynamic arts scene. From intimate live music performances to captivating theater productions, there’s a show for every taste.

Space Music Venue Evanston

A premier live music venue in Evanston offers an intimate setting for diverse performances, blending top-notch acoustics with a vibrant atmosphere.

Writer's Theatre Winnetka

Experience an innovative theatrical production in Winnetka, where over 30 years of cultural excellence bring contemporary, classic, and newly premiered plays to life.

June - Reach New Heights

Soar to new heights with an unforgettable adventure! Climb to the top of a historic lighthouse for stunning lake views or feel the rush on a towering rollercoaster!

Gross Point Lighthouse Evanston, IL

The historic lighthouse in Evanston offers stunning lakefront views, guided tours, and a glimpse into maritime history as one of the oldest lighthouses on the Great Lakes.

Six Flags Gurnee, Chicago Illinois

Enjoy roller coasters, thrilling rides, and a day of fun at Six Flags Great America, just a short drive from the city in Gurnee.

July - Enjoy Local Culture and Food

Summer means festivals, food, and fireworks! Dive into the vibrant scene with outdoor events celebrating local culture, delicious eats, and artistic expression.

Backyard BBQ Wilmette, IL

Explore an interactive cooking experience by taking a hands-on grilling class at the Backyard BBQ in Wilmette.

Ravinia Music Fstival

Ravinia is an internationally renowned music festival that presents outstanding performances by the world’s greatest artists. The enchanting 36-acre park boasts four venues and the popular Lawn, where picnicking is an art.

August - Enjoy the Beach

Soak up the sun along the shores of Lake Michigan. Whether you're lounging on the sand or taking a refreshing dip, it's the perfect way to enjoy summer.

Gillson Beach

Gillson Beach is a peaceful, family-friendly beach in Wilmette with soft sand, scenic views of Lake Michigan. Perfect for swimming, sunbathing, outdoor recreation!

Rent a boat, kayak or stand-up paddleboards at Sailing Beach!

Evanston Beachfront

A popular beach along Lake Michigan, offers lifeguarded swimming and stunning views. The Evanston beachfront is ideal for both relaxation and water activities.

Grab food from Picnic and take it with you to enjoy at the beach.

September - Back to School as an Adult: Expand Your Mind

Embrace the spirit of learning with a visit to The Block Art Museum or immerse yourself in the excitement of a Northwestern University football game. Whether appreciating thought-provoking art or cheering from the stands, there's no shortage of ways to engage and explore.

The Block Museum of Art

The Block Museum of Art on Northwestern University’s campus fosters experimentation, and collaboration and uses visual arts to explore the human experience. By embracing diverse perspectives, the gallery creates shared encounters to deepen understanding of the world and our place in it.

Northwestern University Campus Football

Attend a Northwestern University football where you can cheer on the Wildcats at Ryan Field in Evanston. Enjoy the spirited atmosphere of Chicago’s Big Ten Team!

October - Embrace the Halloween Spirit

Get into the spooky season with haunted houses, costume parties, and eerie walking tours. Celebrate Halloween with thrilling ghost stories, chilling crime tours, and festive Oktoberfest events all around the North Shore.

Pumpkins celebrating Halloween on the North Shore

Whether you want to show off your costume, love a scary haunted house, or want to relax at a fun fall festival with good food and drink, there are plenty of ways to celebrate the season along the North Shore - all tailored to the adult crowd!

North Shore Oktoberfest Events

Celebrate Oktoberfest at multiple North Shore locations, where you can enjoy authentic German food, beer, live music, and festive fall activities perfect for all ages.

November - Cozy Up with Art, Culture, or a Night Away

As the weather cools down, enjoy a cozy date night at a BYOB paint studio, where you can create something special together. Or, treat yourself to a relaxing stay at a local hotel and explore nearby attractions for the perfect getaway.

Deer Path Inn Lake Forest, IL

Plan a romantic getaway at this iconic, English-inspired retreat in Lake Forest. The Deer Path Inn combines timeless charm with modern luxury.

Tipsy Paint BYOB paint studio in Glenview

Enjoy this fun, BYOB paint studio in Glenview, where you can unleash your creativity while enjoying a relaxed, social atmosphere.

December - Boudoir Photoshoot and Holiday Magic

Wrap up the year with a celebration of self-love and holiday cheer. Treat yourself to a boudoir photoshoot that captures your confidence, then embrace the season's magic with a visit to the iconic Home Alone House and other festive displays around the North Shore.

Date night ideas in Chicago with a boudoir photoshoot at Chicago Boudoir Photography

Celebrate your journey with a customized photoshoot at the Chicago Boudoir Photography studio in Winnetka. A boudoir session makes an ideal gift for a partner—or a special treat for yourself!

The Home Alone House in Winnetka, IL

After your photoshoot, visit the iconic Home Alone house to see it beautifully decorated for the holiday season—it’s just a short walk from the Chicago Boudoir Photography studio!

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