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Best Couples Weekend Getaways in Chicago in 2025

Published January 16, 2025 by Amelia
Travel
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Chicago, recognized as the Windy City, is a fantastic destination for couples. If one is planning a perfect weekend getaway with their partner, this place has a lot to offer. It has stunning architecture, delicious food, and a rich culture. Alongside, the beautiful Michigan Lake offers spectacular views. There are several romantic experiences and activities to enjoy here. Continue reading to learn all about weekend getaways in Chicago for couples.

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Weekend Getaways in Chicago for Couples

  •  Get curious on an Architectural Tour

Architectural Tour Chicago

Chicago is famous for its architectural wonders. It is known to be the birthplace of skyscrapers. One could explore the architectural marvels by taking an architectural boat cruise. This is available on the Chicago River. The Chicago Architecture Foundation operates a popular 90-minute cruise. This provides a narrated tour of the city’s architectural history. Along with this, there are other companies with similar tours present.

These boat tours allow couples to spend some quality time together. They get to enjoy the spectacular skyline while learning about the history of the place. For those who believe in good luck, they can get plenty of opportunities to kiss under the bridges along the river. Some cruises even provide romantic sunset options. These include both the view of the Chicago River and Lake Michigan.

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  • Stroll through the Observation Deck

For breathtaking views, couples can visit one of Chicago’s popular observation decks. The Willis Tower, formerly known as the Sears Tower features the famous Skydeck. Meanwhile, the John Hancock Building offers the 360 Chicago observation deck.

Visiting these towers around sunset adds a special touch to the experience. The 360 Chicago Deck even has a bar. Here couples can enjoy a glass of wine or cocktail. They can also take panoramic views of the place and hold hands together. This offers a great view of the lake and the city.

  • Day Date at the Museum

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The city is home to several world-class museums. This makes them a perfect spot for a day-date. Some of them include the Field Museum of Natural History and the Art Institute of Chicago. Alongside, there is the Museum of Science and Industry and the Museum of Contemporary Art.

The Adler Planetarium and the Shedd Aquarium are also located on the Museum Campus. This makes it a great area to explore together. The Museum of Science and Industry is particularly fascinating. It features exhibits like a WWII-era submarine and a weather science room. The Field Museum is known for its high-quality exhibits. It is an excellent choice for couples interested in natural history.

Also read: 7 Best Weekend Getaways In Washington For Family

  • Take a Walk-through Parks

Chicago includes several scenic parks and green spaces. Several of these are closer to the Lake. Millenium Park and Grant Park are two of the most popular spots for a romantic stroll. Millenium Park is home to the famous Cloud Gate sculpture. This is also known as “The Bean”. Alongside, there is also the Jay Pritzker Pavilion and Buckingham Fountain.

Couples can enjoy leisurely walks through these areas. Here, they can relish the sounds and sights of the Windy City. For those who enjoy walking, it is possible to stroll through Millenium Park through Grant Park. This leads all the way to the Museum Campus. This is certainly a day well spent outdoors.

  • Relishing a Deep-Dish Pizza

No trip to Chicago is complete without delving into their famous deep-dish pizza. Many locals and visitors alike recommend Gino’s East. This is also popular for their famous pies. Deep-dish pizza usually takes 45 to 60 minutes to cook. Hence, couples should plan a leisurely meal together.

For those interested in culinary dishes, they can join a food tour. There are several fun activities organized by many food Getaways in Chicago. This can be a fun way to learn the culinary arts while also tasting different styles of pizza. There are several options available at different restaurants.

  • Indulging in Cocktails

Chicago has an exciting bar scene, perfect for couples looking to unwind and relax after traveling. One popular spot is the Signature Lounge, located on the 96th floor of the former Hancock Building. This lounge offers incredible views of the city, making it ideal for enjoying a drink post-dinner.

Moreover, there are other rooftop bars in the city too. This includes the LondonHouse Hotel and Offshore. The latter includes a massive rooftop bar at Navy Pier. These locations offer a romantic ambiance for couples. They can enjoy cocktails while taking in the stunning skyline.

  • Share laughs at Improv Comedy

For a fun night out, couples can enjoy some live improv comedy. The city is home to Second City. This is a renowned improv school and performance center. It has given many famous performers such as Bill Murray and Tina Fey. In addition to Second City, there are numerous other locations in the city with improv shows. 

One highly suggested location is the Shakespeare Company. Here, the cast creates an entirely new play in the style of Shakespeare based on audience suggestions. This unique and entertaining experience is a must-have for couples looking for a light-hearted evening.

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  • Accommodations in Chicago

There are a plethora of affordable and scenic hotels to stay at for couples. One of them is The Langham. This is a luxury hotel known for its exceptional service. It offers beautiful views of the city. Along with this, there is the LondonHouse Chicago. This is a modern downtown hotel. It provides a stylish and comfortable stay. The Viceroy Chicago is located in the Golden Coast Area. This hotel has a mid-century modern vibe. It also includes a rooftop pool.

One of the most historic hotels in the city is The Palmer House. This offers a unique and charming stay for couples. Finally, the Virgin Hotels Chicago is a trendy option too. It caters to a young crowd without crossing the budget. Chicago is well-connected to many cities across the U.S. O’Hare International Airport serves as a major hub. It offers flights to and from major cities, including international destinations. The city is also accessible by bus and train. Therefore, it is easy for couples to plan a weekend Getaways in Chicago.

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Amelia

Amelia, a content writer at tnj.com, specializes in business advice, finance, and marketing. She delivers insightful, actionable content to empower professionals and entrepreneurs.