Weekend getaways from Chicago

Full Guide 2023

Find your ideal getaway...

Boasting award-winning restaurants, elite sports teams, and priceless cultural gems, Chicago is known as the birthplace of the skyscraper. But if you want to get away from the bustle of the third-largest city in the country, there are a ton of getaways that are only a short drive away. Within a weekend, you can travel through rural Illinois or take in the nearby states.

These hand-picked places can let you escape whether you’re planning a romantic weekend in a B&B in a small town or a family vacation at a resort with a water park.

Weekend getaways from Chicago in historic B&Bs

If you are a fan of more simple and historic homes rather than luxurious and expensive hotels, here are a few ideas for a weekend in B&Bs near Atlanta.

Villa D' Citta

This luxurious Italian-style bed and breakfast is located in the well-known Lincoln Park and is ideal for a weekend getaway with your SO or a family getaway. It features a wide variety of dining and entertainment options, a private grotto, and a garden with barbecue grills.

During your stay will feel royal and exceptional thanks to the dark wood furnishings. Large windows, a flat-screen TV, and a private bathroom with opulent toiletries are included in every room. An indoor fireplace and a king-size canopy bed can be found in the Milan Suite. 

Guests adore this house because it boasts an outside sun deck with a hot tub where they can unwind. The Villa provides coffee, tea, and meals for breakfast, lunch, and dinner at the on-site Mangia restaurant.

Washington House Inn

The Washington House Venue in Cedarburg, Wisconsin, combines history, tradition, and casual elegance. In the center of Cedarburg’s historic downtown, this lovely guest house features charming lodgings, superior facilities, exquisite country breakfasts, and gracious service.

Enormous romantic four-poster beds are draped in sumptuous linens and down comforters, private en-suite bathrooms feature whirlpool tubs and walk-in showers, and expansive sitting areas feature comfy couches and gas fireplaces. Large windows let natural light flow into each room.

Every morning, a delicious continental breakfast is provided in the Gathering Room. One of Wisconsin’s most well-liked small-town retreats, the charming town of Cedarburg is known for its abundance of outdoor activities and cultural attractions.

The Herrington Inn & Spa

The Herrington Inn & Spa is a charming boutique hotel located in the scenic town of Geneva, Illinois. The inn features 61 well-appointed guest rooms and suites, each individually decorated with traditional furnishings, plush bedding, and elegant finishes.

The hotel’s full-service spa offers a variety of treatments and services, including massages, facials, and body wraps, as well as a sauna and steam room. Guests can also enjoy the hotel’s fitness center and outdoor pool, which is open seasonally.

The Herrington Inn & Spa is also home to the award-winning Atwater’s Restaurant, which serves farm-to-table cuisine in an elegant setting overlooking the Fox River. The restaurant features an extensive wine list and variety of entertainment options.

Vrooman Mansion B&B

The Vrooman Mansion is a gorgeously restored and furnished mansion that provides guests with an opulent and comfortable stay with access to attractions, restaurants, and stores.

Six guest rooms are available on the site, and each one boasts a distinctive style and amenities. The bigger guest rooms feature a unique theme and are mostly furnished with antiques from the time. Private balconies, fireplaces, and hot tubs are available in a few of the rooms. The Mansion provides five suites and rooms, while the carriage house has two.

Guests can enjoy a gourmet breakfast each morning in the elegant dining room, which features original woodwork and stained glass windows. Also, there is a library and a relaxing sitting area with a fireplace where everyone can unwind.

Weekend getaways from Chicago for couples

If you’re looking for a romantic weekend getaway from Chicago, there are plenty of hotels and resorts that offer couples packages and special amenities. Here are some suggestions:

Mansion Hill Inn

Mansion Hill Inn is a luxury bed and breakfast located in Madison, Wisconsin featuring original beauty and charm.

The inn features seven luxurious guest rooms, each with its own unique decor and amenities. Some rooms boast fireplaces, whirlpool tubs, and private balconies. The inn also offers a private carriage house with a full kitchen and living room, perfect for couples who want additional space and privacy.

Free breakfast is served each morning in the inn’s elegant dining room or on the outdoor terrace. The property also offers afternoon tea, a complimentary wine and cheese reception, and a nightly turn-down service.

Best Western Galena Inn & Suites

Set just a few hours’ drive from Chicago, The Best Western Galena Inn & Suites is a comfortable and affordable hotel located in the historic town of Galena. Guests can enjoy a complimentary hot breakfast each morning, as well as relax at the hotel’s indoor pool, and fitness center.

The hotel features spacious guest rooms and suites, each equipped with modern amenities like flat-screen TVs, private bathrooms, large windows, and more. The Deluxe King Suite with Spa Bath is great for couples because it features a heart-shaped hot tub in room surrounded by mirrors with elegant décor.

The Best Western Galena Inn & Suites is a great choice for couples looking for a comfortable and convenient place to explore the charming town of Galena

Sybaris Pool Suites Indianapolis

Stop here if you’re looking for the greatest romantic getaway for you and your partner. Sybaris, a unique romantic haven, is situated in the center of Indianapolis.

The suites feature a variety of amenities to make your stay special, including a hot tub, a misting system, a cozy fireplace, and your very own private pool with a tropical waterfall. A slide, a steam room, and a massage chair are available in some rooms. On the ceiling, over the king-sized bed, is a mirror with various lights surrounding it. This charming establishment offers couples a romantic spa package.

You can grab a drink or something to eat at bars and restaurants nearby. With hiking and bike routes, guests can explore the area and have an unforgettable adventure

Red Carpet Inn Fanta Suites Hotel

This retro-themed Red Carpet Inn hotel in Greenwood features a number of romantic suites with the greatest romantic amenities for a memorable stay.

Heart-shaped beds, a table with seats, and an extra-large whirlpool are all included in the Alien Invasion Suite. The whirlpool is surrounded by mirrors and lighting for a more private setting. Couples can choose to stay in the Sherwood Forest suite, which boasts a jungle theme, or the Cease’s court suite, which offers a guest hot tub in the bedroom.

On-site amenities include a fitness center and game rooms. Downtown Indianapolis is only several minutes away if you want to go shopping or dining.

Weekend getaways from Chicago for families

Preparing may be difficult, especially when you’re looking for a place to stay that’s fantastic for kids and also allows you to unwind and relax. There are many affordable options offering a cozy stay for the whole family.

Great Wolf Lodge Illinois

Situated only an hour’s drive from Chicago, the Great Wolf Lodge Illinois is a family-friendly resort. The inn features many guest rooms, including suites and family-friendly themed rooms, all of which have cozy furnishings, flat-screen TVs, and mini-fridges.

The resort’s indoor water park, which has a number of water slides, a lazy river, a wave pool, and other water attractions for people of all ages, is the best place to have fun. Together with these additional family-friendly attractions, the resort also comes with a variety of eating choices, a ropes course, a mini-golf course, and an arcade.

The parents can enjoy the adult-only spa and fitness facility. Great Wolf Lodge Illinois is a great option for families looking for a fun and convenient getaway, with plenty of on-site activities and entertainment.

WorldMark Galena

WorldMark Galena is a family resort located in the charming town of Galena featuring spacious one-, two-, and three-bedroom condos with full kitchens, fireplaces, and private balconies or patios.

Guests can enjoy a variety of amenities, including an outdoor pool and hot tub, fitness center, and game room. The resort also comes with outdoor activities like volleyball, horseshoes, and a children’s playground.

WorldMark Galena is a great option for families looking for a relaxing and comfortable getaway with plenty of outdoor activities and sightseeing opportunities. Guests can also explore the surrounding countryside, including the Mississippi River and nearby state parks.

The Abbey Resort

The Abbey Resort is a luxurious resort located on the shores of Lake Geneva in Fontana, Wisconsin. The resort features big guest rooms and suites, each with a private balcony or patio, comfortable furnishings, and modern amenities like flat-screen TVs and free Wi-Fi.

Guests can enjoy a range of activities and amenities, including two outdoor pools, an indoor pool and hot tub, a kids’ pool and playground, a waterslide, a full-service spa, a fitness center, and tennis courts. The resort also comes with a variety of dining options, from casual to fine dining, as well as a waterfront bar and grill.

Lake Geneva offers plenty of opportunities for outdoor recreation, including fishing, boating, and hiking. The hotel is great for families who want to have some fun and be private at the same time.

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark is a popular destination for families looking for a fun and relaxing getaway. The resort features an indoor/outdoor water park with multiple slides and pools, as well as a variety of other amenities.

In addition to the water park, Timber Ridge Lodge features a range of activities for guests of all ages. These include mini-golf, laser tag, a climbing wall, a zip line, horseback riding, and more. The resort also comes with an arcade, a fitness center, and a spa for adults.

The accommodations range from standard rooms to spacious suites and villas. All rooms feature rustic decor and modern amenities such as flat-screen TVs and free Wi-Fi. Rustic furnishings and contemporary conveniences like flat-screen TVs and free Wi-Fi are included in every room. The larger apartments offer living rooms with fireplaces and fully functional kitchens.

Unique cabins for a weekend getaways from Chicago

Although guests appreciate this area for its rich history, culture, and cuisine, if you’re looking for a quick escape from the city, consider staying in a cabin near Chicago where you can enjoy outdoor activities without leaving the property.

The Cozy Cabin

The Cozy Cabin in Bitely is a vacation rental located in the small town of Bitely, Michigan. As its name suggests, it is a cozy cabin-style accommodation that offers a rustic and charming atmosphere for guests.

The cabin features a main living area with a fireplace, a fully equipped kitchen, and a dining area. There are two bedrooms, each with a queen-sized bed. The cabin also features a private bathroom with a shower and a tub.

Outside, guests can enjoy a spacious deck with a grill and seating area, as well as a fire pit for roasting marshmallows or enjoying a campfire. The cabin is surrounded by wooded areas, providing a peaceful and secluded setting.

Cabin Farmhouse

The Gorgeous Farmhouse is a vacation rental property located in a rural area, typically in the countryside. The property features a large, beautifully designed farmhouse with 6 bedrooms, making it suitable for groups or large families.

In addition to the farmhouse, the property also comes with stables and three paddocks, which are ideal for guests who want to bring their horses or go horseback riding. Outside, guests can enjoy a large yard with plenty of space for outdoor activities, such as barbecues, picnics, and games.

Inside the farmhouse, there are spacious living areas, 3 bathrooms, a fully equipped kitchen, and comfortable bedrooms with plenty of space for everyone to relax and unwind. The farmhouse is decorated in a rustic, farmhouse style with modern amenities such as Wi-Fi and flat-screen TVs.

The Wüdenknipple

The Wüdenknipple, which is situated in Bessemer, is an amazing cabin for a family of 4. The vacation property features free private parking and is located in a region where guests may go hiking, skiing, and cycling.

Two bedrooms, one with a king-sized bed and one with 2 small separate beds, a kitchen with a refrigerator, a flat-screen TV, a lounge area, and one bathroom with a shower are all included in this small cozy cabin.

Guests are welcome to use the outdoor private hot tub and relax after a long day exploring the area. Together with a ski pass sales desk and a ski storage area, the Wüdenknipple features a BBQ and sun terrace.

Rippling River Resort

Situated in Marquette Rippling River Resort is an ideal destination for couples looking to escape into nature and have some peace and romance alone.

The resort offers a variety of indoor and outdoor activities in addition to its on-site Riverside Bar & Grill restaurant. The cabin features one bedroom with a king-sized bed, one bathroom, and a fully-equipped kitchen. Guests can relax in the outdoor pool near the cottage.

Fishing, kayaking, hiking, swimming, and camping are just a few of the activities and amenities available at the resort. Also, the cabin comes with cottages, RV sites, and tent camping areas for guests to use.

Afforable weekend getaways from Chicago

Affordable rooms and seasonal packages are available at numerous neighboring hotels, resorts, and charming inns. There are many options available, whether you want to go hiking, biking, shopping, or simply unwind on the beach.

Grand Geneva Resort

Featuring two championship golf courses, a ski resort, room service, many pools, a spa, and a variety of dining and entertainment options, Grand Geneva Resort and Spa is a luxury resort for every taste and age.

The modern rooms come with a private balcony with panoramic views. They also include modern amenities such as flat-screen TVs, high-speed internet, and plush bedding. 

In addition to its golf and skiing facilities, Grand Geneva Resort and Spa feature a variety of activities and amenities for guests of all ages, including hiking and biking trails, indoor and outdoor pools, and a fitness center. Guests can also enjoy fine meals at several dining options, including a steakhouse, an Italian restaurant, a sports bar, and a cafe.

Knickerbocker on the Lake

If you want to stay in a historic hotel with city views, Knickerbocker on the Lake is located in a vibrant area of Milwaukee and is within walking distance of many restaurants, bars, and shops. It is also close to popular attractions.

All suites are elegantly appointed with a blend of modern and historic decor. They come with flat-screen TVs and a private bathroom. Some rooms also feature lake views or balconies

Knickerbocker on the Lake comes with a variety of amenities for guests, including a fitness center, and a rooftop terrace with panoramic views of Lake Michigan and the city skyline. The on-site restaurant, The Knick, serves contemporary American cuisine and craft cocktails.

More weekend getaways near Chicago

If you’re looking for more amazing getaways near Chicago, here you can find our top recommendations in the area.

For more unique accommodations in Il, visit our Romantic guide – Illinois!


  • What are the best outdoor activities to do on a weekend getaway from Chicago?

    There are so many amazing natural beauties within a minutes from Chicago such as Lincoln park and lake Geneva. Enjoy your time outdoors by hiking, camping, fishing, horse riding, and more. 

  • Are there weekeng getaways from Chicago for couples?

    There are amazing places available for couples near Chicago. We have collected the best hotels for couples only. The Best Western Galena Inn is a comfortable hotel featuring rooms with a heart-shaped hot tub surrounded by mirrors. Also, Sybaris Pool Suites provide amazing romantic room amenities including a hot tub, a fireplace, a private pool with a tropical waterfall, a massage chair and so much more. 

  • Which weekend getaways from Chicago are the best for families?

    Many hotels near Chicago provide something for families such as a kids' pool, children's playground, and kids' meals. For example, the great Wolf Lodge features an amazing indoor water park with a number of water slides, a lazy river, and a wave pool. The Timber Ridge Lodge is another stunning hotel for all ages because it comes with an indoor/outdoor water park with multiple slides and pools, as well as mini golf, laser tag, a climbing wall, and more.

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