Top 5 Things To Do On A First Date In Chicago

Connorbeard
3 min readJun 20, 2024

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Top 5 Things To Do On A First Date In Chicago

1. Navy Pier

Start your romantic journey at Navy Pier, an iconic landmark offering stunning views of Lake Michigan. Take a leisurely stroll along the pier, explore the shops, and enjoy a ride on the Ferris wheel, where you can cozy up and enjoy breathtaking cityscape views.

For more adventurous couples, consider taking a boat tour departing from the pier, offering a unique perspective of Chicago’s skyline from the water.

Don’t miss: The Centennial Wheel at sunset, offering a picturesque backdrop for a memorable first date photo.

Affiliate link: Book a boat tour at Navy Pier

2. Art Institute of Chicago

Immerse yourselves in culture and creativity at the Art Institute of Chicago. Wander through the galleries hand-in-hand, discussing your favorite pieces of art. The museum’s serene gardens also provide a quiet spot for introspective conversations.

Tip: Visit on Thursday evenings for free admission, perfect for budget-conscious daters.

Affiliate link: Explore art tours at the Art Institute

3. Millennium Park

Millennium Park offers a blend of nature, art, and architecture, making it an ideal spot for a first date. Take a romantic stroll through the Lurie Garden, or snap a selfie in front of the famous Cloud Gate sculpture, lovingly nicknamed “The Bean.”

During summer evenings, catch a free concert or movie at the Jay Pritzker Pavilion, adding a cultural touch to your date night.

Affiliate link: Plan a guided tour of Millennium Park

4. Chicago Riverwalk

For a scenic and relaxing date, explore the Chicago Riverwalk. This picturesque promenade offers stunning views of the city’s architecture and riverfront. Stop by a riverside café for a casual drink or bite to eat, or rent a kayak and paddle along the river together.

Insider tip: Visit during sunset for a magical ambiance with the city lights reflecting on the water.

Affiliate link: Check out river cruises on the Chicago River

5. Lincoln Park Zoo

Experience wildlife and nature at Lincoln Park Zoo, one of the oldest zoos in the country. Wander through lush gardens and observe a variety of animals, from playful primates to majestic big cats.

After exploring the zoo, stroll through Lincoln Park itself, known for its peaceful paths and charming scenery.

Affiliate link: Discover zoo tours and activities

Chicago offers endless possibilities for a memorable first date. Whether you prefer cultural outings, scenic views, or leisurely walks, these top 5 spots ensure a romantic and unforgettable experience.

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