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Top Things to Do in Chicago for Couples

Top Things to Do in Chicago for Couples

James Miller, GetTransfer.com
by 
James Miller, GetTransfer.com
6 minutes read
News
October 16, 2025

Introduction: Discover the Romantic Charm of Chicago

Are you searching for wonderful things to do in Chicago for couples? This vibrant city is filled with romantic spots, exciting activities, and beautiful scenery, making it an ideal destination for couples looking to create lasting memories. Whether you want to relax in a park, enjoy a romantic dinner, or explore the arts and culture, Chicago offers countless options to delight both you and your partner. In this guide, we will highlight some of the top attractions and experiences perfect for couples visiting the Windy City this weekend.

Why Rent a Car with GetRentaCar?

To maximize your experience in Chicago, consider renting a car to make getting around easier. Here are several benefits of choosing GetRentaCar as your transportation option:

  • Convenience: Navigate Chicago’s attractions with ease and convenience, particularly if you’re planning to explore areas beyond downtown.
  • Comfort: Enjoy a spacious vehicle that accommodates your needs and provides a comfortable ride for your romantic getaway.
  • Cost Savings: GetRentaCar offers competitive pricing, ensuring that you can stick to your budget while enjoying a premium travel experience.

Outdoor Activities and Experiences

Chicago’s beautiful parks and waterfront make it a fantastic location for outdoor activities. Here are some top choices for couples:

1. Millennium Park

One of the best things to do in Chicago for couples is to visit Millennium Park. Enjoy the iconic Cloud Gate sculpture, also known as “The Bean,” and take memorable photos with your partner. The surrounding gardens and open spaces are perfect for leisurely walks or picnics!

2. Visit Navy Pier

Navy Pier is another quintessential Chicago experience. Couples can stroll along the pier, enjoy rides on the Ferris wheel, or dine at one of the many restaurants with stunning lake views. The park frequently hosts outdoor events, making it a lively spot to visit.

3. Take a Sunset Cruise on Lake Michigan

For a romantic outing, consider taking a sunset cruise on Lake Michigan. This unforgettable experience allows couples to enjoy stunning views of the Chicago skyline while savoring quality time together. Enjoy the beautiful colors of the sunset as you cruise the lake, creating memories to cherish.

Art and Cultural Experiences

Chicago is known for its rich arts and culture scene. Don’t miss these attractions:

4. The Art Institute of Chicago

The Art Institute is one of the top museums in the country and is home to an extensive collection of artworks. Explore famous pieces by Monet, Van Gogh, and many others while enjoying the gorgeous architecture. This cultural experience is a wonderful activity for couples who appreciate art.

5. Explore the Theater District

Chicago’s Theater District is bustling with life and offers a variety of shows, including musicals, plays, and more. Check out the schedule to see if there’s a performance you and your partner would love. An evening at the theater makes for a fantastic date night!

Family-Friendly Activities

If you’re visiting Chicago with kids, there are plenty of activities to engage the whole family:

6. Lincoln Park Zoo

Lincoln Park Zoo offers free admission, making it a budget-friendly option for families. Home to a wide variety of animals, this zoo is perfect for a fun day out with the kids. Explore the exhibits, enjoy picnic areas, and create meaningful family experiences.

7. The Museum of Science and Industry

The Museum of Science and Industry is one of the largest science museums in the world. It features hands-on exhibits, live demonstrations, and activities that will thrill both kids and adults. A visit is not only educational but also incredibly entertaining, making it a top pick for family outings.

Dining Options for Couples and Families

After a day of exploring, refueling is essential. Here are some ideal dining spots:

  • Girl & The Goat: This popular restaurant by Chef Stephanie Izard features creative dishes designed for sharing, making it perfect for couples and families who want to try a bit of everything.
  • Portillo’s: A Chicago staple, Portillo’s is known for its delicious Italian beef sandwiches and iconic Chicago-style hot dogs. It’s a family-friendly spot that everyone will love.
  • Lou Malnati’s Pizzeria: Don’t miss trying Chicago’s famous deep-dish pizza at Lou Malnati’s. The family-friendly atmosphere makes it a great spot for dinner or lunch.

Indulge in Local Desserts

After a hearty meal, try some local sweet treats at one of Chicago’s many bakeries or ice cream shops. Sampling regional desserts adds a delightful touch to your culinary adventure in the city!

Free and Budget-Friendly Activities

Exploring Chicago doesn’t have to be costly. Here are some enjoyable free or low-cost activities:

8. Visit the Chicago Riverwalk

The Chicago Riverwalk is a beautiful place to take a leisurely stroll. Enjoy the public art installations, grab a bite from local vendors, or simply relax while admiring the scenery. It’s one of the best things to do in Chicago without spending money.

9. Attend Free Local Events

Chicago hosts various free events year-round, including festivals, art fairs, and concerts. Keep an eye out for local listings to find events that coincide with your visit, offering unique experiences you won’t want to miss.

Seasonal Events and Festivals

Throughout the year, Chicago is filled with exciting seasonal events that cater to families and couples:

10. Chicago Blues Festival (June)

Celebrate the city’s rich music heritage at the Chicago Blues Festival. Enjoy live performances from local and national artists in a festive atmosphere. It’s perfect for music lovers looking to enjoy quality performances.

11. Chicago Christmas Market (December)

During the winter holiday season, don’t miss the Chicago Christmas Market, featuring festive decorations, local crafts, and delicious seasonal treats. Families can enjoy holiday activities while experiencing the festive spirit of Chicago.

Planning Your Trip to Chicago

To ensure a smooth and enjoyable visit, consider these practical tips:

  • Book Accommodations Early: Popular hotels and rentals can fill up quickly, especially during peak seasons, so secure your stay ahead of time.
  • Use Public Transportation: Chicago’s public transportation system is a great way to navigate the city. Consider purchasing passes for unlimited travel during your visit.
  • Pack for the Weather: Depending on when you visit, be sure to pack layers, especially if visiting in the winter or spring months when temperatures can fluctuate.

Conclusion: Experience the Vibrance of Chicago

In conclusion, Chicago offers a wealth of exciting things to do in Chicago that cater to couples, families, and solo travelers alike. With its rich history, stunning architecture, and vibrant cultural scene, you’re sure to create memorable experiences. Don’t forget to leverage GetRentaCar to help manage your travel plans effectively and explore every charming corner of this dynamic city. Start planning your trip to Chicago today and get ready to embark on an unforgettable adventure!

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