Escape With Your Partner: Top Romantic Weekend Getaways Chicago

Romantic Weekend Getaways Chicago

For the B&B Lovers – Escape from the hustle and bustle of the city with a stay at a cozy bed and breakfast. Enjoy a romantic weekend getaway in the countryside, relaxing in antique-filled rooms, exploring nearby attractions, and indulging in delicious homemade breakfast.

For the Couple Seeking Pure Romance – Set the mood for a romantic weekend escape by booking a stay at a luxury hotel in the city. Spend the days exploring chic boutiques and galleries, then return in the evening for a romantic dinner and a night full of pampering.

For the Couple Who Loves History – Let the city’s past come alive with a visit to one of Chicago’s iconic historic districts. Stroll through cobblestone streets, admire turn-of-the-century architecture, and explore the city’s vibrant cultural attractions.

For the Luxury-Minded Couple – Get away from it all with an indulgent weekend escape to one of Chicago’s iconic luxury hotels. Enjoy a romantic dinner at the hotel’s fine-dining restaurant, unwind with a spa day, and relax in the hotel’s luxurious rooms.

For the Outdoorsy Couple – Take your outdoor adventures to the next level with a romantic weekend getaway in the majestic mountains, forests, and trails of the Midwest. Spend days exploring nature, kayaking down a river, and camping out under the stars.
For the Sightseeing Couple – Embark on a romantic sightseeing tour of Chicago’s most iconic attractions. Cruise along the city’s famous lakefront, take in the city’s vibrant skyline, and explore the city’s many museums and galleries.



For the Wine Lovers – Spend the weekend sipping, sampling, and savoring the finest wines from the area’s renowned wineries. Take a tour of the vineyards, explore the tasting rooms, and take home your favorite bottles.

For the B&B Lovers

If you’re looking for a romantic weekend away from Chicago with your partner, B&B’s are a great option. From cozy cabins nestled in the woods to restored Victorian homes overlooking the lake, there’s something for every couple looking for a romantic getaway in the Chicago area. Here are some of the best B&B’s for couples looking to reconnect and escape the hustle and bustle of the city.

Butterfly Farm Bed & Breakfast – Located in Woodstock, IL, Butterfly Farm Bed & Breakfast is the perfect destination for couples looking for a relaxing weekend getaway. This beautiful B&B is situated on 5 acres of woodland and is surrounded by nature and tranquility. Spend the day exploring the trails and observing hundreds of butterflies. In the evening, enjoy dinner at the onsite restaurant or relax in the spa.

The Farmhouse B&B – Located just an hour away from Chicago, The Farmhouse B&B is a perfect place to escape for a romantic weekend. This stunning estate offers guests a chance to relax in a beautiful and peaceful setting. Enjoy views of the countryside from the deck, or take a stroll through the gardens. If you’re feeling adventurous, explore the nearby hiking trails or take a leisurely bike ride.

Lacock House Bed & Breakfast – This charming Victorian-style B&B is located just outside of Chicago and is the perfect place for couples looking to reconnect. Enjoy the serenity of the lush gardens, take a romantic walk on the nearby trails, or explore the nearby historic sites. In the evening, take advantage of the onsite restaurant and spa services.

The Red Barn Inn – The Red Barn Inn is located in the heart of the countryside, offering guests the perfect place to relax and reconnect. Enjoy the peaceful atmosphere of the Inn, or take a walk around the nearby lake. In the evening, cozy up by the fireplace and enjoy the beautiful sunset views.

The Willows Bed & Breakfast – If you’re looking for a cozy and romantic weekend getaway from Chicago, The Willows Bed & Breakfast is the perfect destination. This quaint B&B is located just outside of the city and offers guests a chance to escape the hustle and bustle of the city. Enjoy the views of the countryside, take a stroll through the gardens, or explore the nearby trails.
No matter what type of romantic weekend getaway you’re looking for, you’ll be sure to find a perfect B&B near Chicago. With so many options to choose from, you’re sure to find the perfect place to reconnect with your partner this weekend.

For the Couple Seeking Pure Romance

Romantic Riverfront Cabins on the Wabash River
If you’re looking for the perfect weekend getaway that’s all about romance, then look no further than Chicago! From serene lakeside retreats to luxurious spa experiences, there are plenty of options to choose from for you and your partner.

  • The Peninsula Chicago – Located in the heart of the city, this chic hotel offers luxurious amenities, fine dining, and world-class spa treatments to ensure a romantic experience.
  • The Drake Hotel – This iconic hotel offers sophistication and romance. Enjoy a stroll through the hotel’s gardens and take in the stunning city views.
  • Ritz-Carlton Chicago – Spend a weekend lounging in the hotel’s spa, dining in the lavish restaurants, and exploring the city.
  • Allgauer’s on the Riverfront – This lakeside retreat offers seclusion and serenity. Unwind in the spa, take in the views of the Chicago River, and enjoy a romantic dinner at the restaurant.
  • The Langham Chicago – This luxury hotel offers a unique combination of old-world elegance and modern amenities. Enjoy the hotel’s spa, dine in the fine restaurants, and take in the stunning views of the city.

No matter what kind of romantic getaway you’re looking for, there are plenty of options near Chicago to choose from. Whether you want to stay in the heart of the city or escape to a secluded lakeside retreat, you’ll find the perfect place to have a romantic weekend.

For the Couple Who Loves History

Chicago is rich in history and culture, and it’s a great place to explore with your partner. Whether you’re looking for a quiet weekend away from the hustle and bustle of the city, or you want to explore some of the historical sites around the city, Chicago has something for everyone.

Historic Hotels
The Drake Hotel is a classic Chicago landmark that has been around since 1920. This hotel’s luxurious rooms, top-notch service, and beautiful architecture make it the perfect place to stay for a romantic weekend getaway.

The Hotel Burnham is another historical Chicago hotel with a special setting. Located in the heart of the Loop, this hotel has been around since 1895 and is a great place to escape from the hustle and bustle of the city and enjoy a romantic retreat. The hotel’s old-world charm will make you feel like you’ve stepped back in time.

Historic Attractions
Chicago is home to many historic attractions, including the Field Museum, Shedd Aquarium, and Art Institute. These are great for couples who want to explore the city’s history and culture.
The Lincoln Park Conservatory is another great historic attraction to explore with your partner. This conservatory was built in the late 1800’s and is home to a variety of plants and flowers.

Couples Cooking Classes
If you and your partner are looking for a unique experience, consider taking a cooking class together. Couples cooking classes are a great way to spend the weekend in Chicago and learn new skills. You’ll be able to explore the city’s food culture, create delicious meals, and learn some new skills that you can use in your own kitchen.

Historic Tours
Chicago has a rich history, and there are many historic tours available throughout the city. From the classic Chicago Architecture Tour to the Chicago River Cruise, there are plenty of ways to explore the city’s past with your partner.

Historic Restaurants
Chicago has many historic restaurants that are perfect for a romantic date night. Check out the Green Door Tavern, which has been around since 1872, or the Berghoff Restaurant, which has been a staple of Chicago’s Loop since 1898. Enjoy classic dishes and explore the city’s past together.

No matter what type of history you and your partner are into, there is plenty to explore near Chicago. These romantic weekend getaways are perfect for exploring the city’s history, enjoying delicious food, and spending some quality time together.

For the Luxury-Minded Couple

If you’re looking for a luxurious weekend getaway, Chicago is the place to be. With its numerous high-end hotels, fine dining restaurants, and cultural attractions, the city offers something for everyone. From luxurious spa treatments to gourmet meals, you’re sure to find the perfect way to relax and unwind during your romantic getaway.

  • Chicago City Suites: Indulge in the height of luxury at the 5-star Chicago City Suites. Boasting gorgeous lake-facing views, the suites offer plush bedding, deluxe furnishings, and all the amenities you could ever hope for. The hotel also features a world-class spa, so you can get pampered in style.
  • The Peninsula Hotel: The Peninsula is a stunning 5-star luxury hotel located in the heart of the city. From its exquisite on-site spa and pool to its opulent restaurants and bars, you’ll be able to wine and dine in style. Plus, the hotel offers a complimentary chauffeur service, so you can explore the city in the utmost comfort and convenience.
  • The Langham: The Langham is a magnificent 5-star hotel located in the heart of the city. Whether you’re looking to indulge in a luxurious spa treatment, enjoy an exquisite five-course meal, or simply relax in a plush suite, you’ll find it all at The Langham.
  • The Drake: If you’re looking for an iconic luxury hotel, look no further than the Drake. With its elegant decor, beautiful furnishings, and exquisite cuisine, The Drake offers the perfect retreat for a romantic weekend getaway. Plus, the hotel is located just steps away from some of the city’s best shopping and entertainment destinations.

When it comes to luxurious weekend getaways, Chicago has something for everyone. Whether you’re looking for an intimate spa retreat or a romantic dinner for two, there’s something for everyone. Whether you’re looking for a relaxing escape or an adventure-filled weekend, you’re sure to find the perfect weekend getaway in the Windy City.

For the Outdoorsy Couple

If you and your partner are nature lovers, then Chicago has plenty of idyllic weekend getaways for you to explore. Whether you’re looking for a scenic escape in the woods or an outdoor adventure, here are a few romantic getaways in the area to consider:

  • Starved Rock State Park – Located near Utica, Illinois, Starved Rock State Park offers stunning views of the Illinois River and a plethora of outdoor activities for couples to enjoy. From hiking and fishing to boating or just enjoying the scenery, there’s something for everyone. Plus, there are plenty of options for camping and lodging nearby so you can make the most of your getaway.
  • Barrington Hills – Located in the northwest suburbs of Chicago, Barrington Hills provides the perfect backdrop for an outdoor getaway with your partner. From horseback riding and golfing to hiking and fishing, this area offers plenty of ways to explore the great outdoors. Plus, the area also has some great restaurants, shops, and galleries to explore as well.
  • Kankakee River State Park – Located south of Chicago, the Kankakee River State Park is a great destination for couples who love the outdoors. The park offers over 80 miles of trails for hiking, biking, and horseback riding, as well as plenty of opportunities for bird watching, boating, and fishing. Plus, the area also has plenty of campgrounds and cabins for a romantic getaway.
  • Galena, Illinois – Located near the Wisconsin border, Galena is the perfect destination for an outdoor romantic getaway. With plenty of trails for hiking, biking, and horseback riding, as well as golf courses, fishing spots, and scenic overlooks, you and your partner will be able to enjoy the great outdoors together. Plus, the area also has plenty of restaurants, shops, and entertainment for a complete weekend escape.

No matter which destination you decide on, a romantic weekend getaway near Chicago is sure to be an experience to remember. From the beloved Starved Rock State Park to the charming town of Galena, Illinois, there are plenty of ways to explore the great outdoors with your significant other. So, grab a map and start planning your perfect romantic getaway!

For the Sightseeing Couple

If you’re looking for a romantic getaway in Chicago with plenty of sightseeing opportunities, then look no further. There are plenty of nearby destinations that offer fantastic views and interesting attractions. From the city of Chicago itself to nearby historic towns, you and your partner will be able to find just the right spot for your romantic weekend getaway. Here are some of the best spots for sightseeing couples.

Chicago

Chicago is a must-see getaway for sightseers. With its iconic skyline and unparalleled lakefront views, Chicago offers a wealth of activities and attractions for couples. The city is home to many world-class museums, including the Art Institute of Chicago, the Museum of Science and Industry, and the Field Museum of Natural History, as well as the Shedd Aquarium. Take a stroll along the Magnificent Mile or explore Navy Pier. For a romantic night out, check out the restaurants, clubs, and lounges along the River North area, or take a romantic boat tour on Lake Michigan.

Galena, Illinois

Galena, Illinois, is a historic town located about two hours from Chicago. There are plenty of sightseeing opportunities in this charming town, including the Galena Historic District, the U.S. Grant Home, the Galena River, and the Galena River Trail. While in town, you can explore the shops and restaurants in the downtown district or take a scenic drive and explore the surrounding countryside. Don’t forget to check out the many wineries and tasting rooms in the area, as well as the Jo Daviess County Historical Museum.

Starved Rock State Park, Illinois

Starved Rock State Park is a picturesque spot located about two and a half hours from Chicago. This beautiful park is home to stunning sandstone bluffs, canyons, and waterfalls. You can explore the park’s numerous trails, take a boat tour on the Illinois River, or go horseback riding. For a romantic night out, head to the lodge and dine on their award-winning cuisine. For an extra special evening, book a romantic cabin in one of the park’s camping areas.

St. Charles, Illinois

St. Charles, Illinois, is a historic town located about an hour west of Chicago. This town is home to many charming attractions, including the St. Charles Historic District, the Fox River, and the Lincoln Park. Spend your day exploring the shops and galleries along Main Street or head to the Prisco Community Center for a romantic walk around the pond. For a special evening, take a romantic gondola ride down the Fox River or enjoy dinner at the Arcada Theatre.

Michigan City, Indiana

Michigan City, Indiana, is a historic beach town located about two hours from Chicago. This quaint town is home to the iconic Washington Park Beach, the Michigan City Lighthouse, and the Michigan City Zoo. Spend your day exploring the shops and restaurants in the downtown area or take a romantic stroll along the lakefront. For a special evening, head to the nearby casino to try your luck or take a romantic sunset cruise on the lake.

For the Wine Lovers

If you and your partner are all about the vino, then there are plenty of options for romantic weekend getaways near Chicago that are sure to please. From quaint bed and breakfasts to luxurious vineyards, the Windy City area has everything you need to enjoy a romantic weekend in the countryside while sampling some of the best wines around.

Bed and Breakfasts: Whether you’re seeking a cozy and intimate setting, or something a bit more opulent, there are several bed and breakfasts that provide exclusive wine-tasting experiences. La Banque Hotel in Galena, Illinois, offers a Wine & Cheese experience that includes a private tasting with the Sommelier, as well as a cheese plate and a bottle of their finest house wine. The Lakehouse Inn in Williams Bay, Wisconsin, provides a complimentary wine tasting, as well as a selection of wines to purchase for an additional fee.

Vineyards:
If you’d prefer to get away and still enjoy the best of the area’s vino, then a weekend at a nearby vineyard is the way to go. The Heineman Winery in Geneva, Illinois, offers a variety of options including a deluxe wine tasting package, which provides a tour of the vineyards, a five-wine tasting, and a cheese plate. The Lynfred Winery in Roselle, Illinois, boasts a vineyard tour, a tasting of five wines, and a cheese plate for two. And the Timber Hill Winery in Pecatonica, Illinois, offers a wine tasting paired with charcuterie and artisan cheeses.

Local Wineries:
Don’t forget to check out some of the local wineries near Chicago. The City Winery in downtown Chicago is a great place to start, offering a variety of wine tastings and events including a romantic Valentine’s Day package that provides a three-course dinner and a bottle of wine. The Tasting Room in Lincoln Square offers an extensive selection of wines, as well as a “Wine Lover’s Package” that includes a cheese board and a bottle of wine. And the Urban Cellars in the West Loop offers a great selection of wines and tastings paired with small bites.

Whether you’re an oenophile or just looking for a romantic weekend away, there are plenty of options for a wine-filled getaway near Chicago. From cozy bed and breakfasts to luxurious vineyards, you’re sure to find the perfect destination for your romantic weekend.

What is the best time of year to take a weekend getaway from Chicago?

Chicagoans seeking a romantic weekend getaway have plenty of options when it comes to timing. With its temperamental weather, it’s important to time your getaway right to make sure you get the most out of your experience. Here’s a look at the best times of year to escape to one of the many romantic getaways near Chicago.

Spring: As the snow melts and the temperatures rise, spring can be the perfect time to enjoy the outdoors together. The vibrant colors of flowers in bloom, plus the balmy weather make it ideal for taking long romantic walks or bike rides. Plus, there are plenty of outdoor activities available such as kayaking, paddle boarding, and more.

Summer: The hot summer months can be ideal for a romantic getaway near Chicago. Whether you’re looking for a beach escape or a weekend trip to the mountains, summer is the perfect time to take advantage of all the area has to offer. Take romantic strolls along the lakefront, explore the downtown area, or enjoy some of the many festivals and cultural events.

Fall: As the leaves change color and the temperatures cool, fall is a great time to enjoy a romantic weekend getaway. The mild weather and the beauty of the changing foliage create a romantic atmosphere. Enjoy apple picking, hikes, and cozy nights in front of the fire.

Winter: While the colder months can be intimidating for some, there are plenty of activities available for a romantic winter getaway. Enjoy a cozy night in together, take romantic winter strolls, or explore the city’s many Christmas markets. Plus, for those looking for a more adventurous experience, winter offers the perfect opportunity for skiing, snowshoeing, and other winter sports.

No matter what time of year you choose to escape from Chicago, there are plenty of romantic getaways that offer something for every couple. Whether you’re seeking relaxation, adventure, or something in between, you’re sure to find the perfect weekend getaway near Chicago.

  • For the B&B Lovers: Enjoy a cozy getaway in one of many bed and breakfasts near Chicago. Spend time snuggling up with your partner while exploring the surrounding area. Popular activities near B&Bs include wine tastings, outdoor trails, and historical sites.
  • For the Couple Seeking Pure Romance: Get swept away in a romantic getaway near Chicago. Treat yourselves to a luxurious dinner with views of the city skyline. You can also book a couple’s massage or take a romantic horse-drawn carriage ride.
  • For the Couple Who Loves History: Treat yourselves to a romantic weekend getaway at one of the many historical sites near Chicago. Visit the Field Museum, the Art Institute of Chicago, or one of the city’s many parks and gardens.
  • For the Luxury-Minded Couple: Enjoy a luxury getaway to a nearby spa or resort. Take advantage of the many amenities available, such as fine dining, spa treatments, and swimming pools.
  • For the Outdoorsy Couple: Get away from the hustle and bustle of the city and explore the great outdoors. Enjoy a romantic hike at the nearby Starved Rock State Park or kayaking on the Fox River.
  • For the Sightseeing Couple: Get lost in the beauty of Chicago’s skyline. Take a ride on the city’s historic ferris wheel or plan a romantic helicopter tour of the city.
  • For the Wine Lovers: Take a romantic weekend getaway to one of the many wineries near Chicago. Enjoy a romantic picnic with breathtaking views and sip on delicious wines.

No matter which type of weekend getaway you choose, there are plenty of activities available to make your experience special. From romantic dinners to outdoor adventures, you and your partner can find the perfect getaway near Chicago. The best time of year to take a romantic weekend getaway from Chicago is typically spring and fall when the weather is mild and the attractions are in full bloom.

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