Weekend Getaways from Chicago

Location: Lake Geneva, Wisconsin

Looking for a getaway that blends upscale relaxation with all-ages adventure? Grand Geneva Resort and Spa has you covered. Perfectly placed between Chicago and Milwaukee, this scenic resort is a go-to for couples, families, and anyone who wants a mix of spa time, outdoor fun, and cozy comfort in one spot.

• Great for All Seasons – Whether you're golfing in summer or skiing in winter, there's always something fun to do
• Family-Friendly Fun – Kids will love Moose Mountain Falls Waterpark with 50,000 square feet of waterslides, lazy river, hot tubs, and lounge areas
• Outdoor Adventures – Enjoy lake cruises, historic walking tours, and shopping excursions around charming Lake Geneva
• Winter Wonderland – Hit the slopes at The Mountain Top for downhill skiing, snowboarding, or peaceful cross-country trails
• Couples’ Escape – Indulge in spa treatments, romantic dinners, and beautiful views made for reconnecting
• Easy to Get To – Located in Lake Geneva, just a short drive from both Chicago and Milwaukee

Address: Grand Geneva Resort and Spa, 7036 Grand Geneva Way, Lake Geneva, WI 53147
Phone: 262-248-8811

Grand Geneva Resort and Spa offers something special for every season—book your stay and experience Wisconsin’s ultimate resort escape!

Location: Acme, Michigan

Looking for a family-friendly escape that has something for everyone? Grand Traverse Resort and Spa sits on 1,400 gorgeous acres near Lake Michigan and is packed with ways to relax, play, and explore. Whether you're hitting the golf course, booking a spa day, or enjoying lake views from your condo, this Northern Michigan resort is a fantastic pick for weekend getaways or full-on family vacations.

• All-Ages Appeal – From beachside walks to championship golf, there’s something here for kids, couples, and everyone in between
• Premier Golf – Tee off on one of four 18-hole courses, including The Bear by Jack Nicklaus and The Wolverine by Gary Player
• Massive Spa Complex – Enjoy 100,000 square feet of wellness with pools, whirlpools, sauna, tennis, fitness classes, and a peaceful relaxation room
• Comfortable Accommodations – Stay in a cozy Tower Room with panoramic lake views, a condo by the golf course, or a convenient hotel room near the action
• Dining On-Site – Multiple restaurants serve up everything from casual bites to refined fare—no need to leave the resort
• Great Deals – Planning a last-minute escape from Chicago? Be sure to ask about seasonal specials and packages

Address: Grand Traverse Resort and Spa, 100 Grand Traverse Resort Village Blvd, Acme, MI 49610

Grand Traverse Resort and Spa is a lakeside favorite for families, couples, and golfers alike—book your escape today and discover why it’s a Midwest must!

Location: Fontana-On-Geneva Lake, Wisconsin

Planning a relaxing weekend escape that doesn’t skimp on fun or comfort? The Abbey Resort is a full-service lakeside retreat just a short drive from Chicago. Set on 90 scenic acres by Fontana Harbor, this resort offers everything from spa treatments and lakefront dining to family-friendly activities and cozy accommodations—making it a favorite for couples, families, and friends alike.

• Spacious Resort Grounds – Nestled on 90 acres with beautiful harbor views, perfect for lakeside strolls and morning coffee with a view
• Comfortable Accommodations – Choose from 334 deluxe guestrooms, 13 spacious suites, or 13 private villas for a more secluded stay
• Avani Spa Escape – Unwind with massages, facials, body wraps, aromatherapy, saunas, and more inside the 35,000-square-foot spa
• Fun for Everyone – Take a dip in indoor/outdoor pools, break a sweat in the aerobics studio, or challenge the family to disc golf or arcade games
• Diverse Dining Options – Enjoy everything from gourmet meals at 240 West to casual lakeside bites at The Waterfront Restaurant & Grill
• Active Adventures – Try water sports, biking, nearby golf, or leisurely lakefront walks—there’s plenty to keep you moving
• Convenient & Affordable – Just a quick trip from Chicago, The Abbey makes for an easy, budget-friendly weekend escape

Address: The Abbey Resort, 269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125

The Abbey Resort is ready to welcome you for a weekend of lakeside luxury, fun, and total relaxation—book your stay today!

Location: Egg Harbor, Wisconsin

For a stress-free Door County escape with plenty to do (or not do!), The Newport Resort in Egg Harbor is a top pick. Whether you're traveling with the family or planning a quiet romantic retreat, this cozy, well-equipped resort offers comfort, convenience, and access to everything that makes Door County so special—from scenic beaches to charming local shops and restaurants.

• Family-Friendly Vibes – Relaxed and welcoming, with 59 rooms and suites perfect for couples or the whole crew
• Beach Nearby – Just minutes from sandy shores—bring your towels and beach toys!
• Comfy Suites – Whirlpool tubs, kitchenettes, and cozy sitting areas make your stay feel like home (but better)
• Great Indoor Perks – Heated indoor pool, fitness center, game room, quiet library, and cozy lounge space
• Peaceful Outdoor Spaces – Enjoy a stroll through the garden or relax in the fresh air with a good book
• Walkable Dining – Restaurants and local eateries are just steps away in the heart of Egg Harbor
• Year-Round Fun – Summer means beaches, golf, and state park hikes; winter brings snowshoeing, skiing, and sledding
• Ideal for All Travelers – Whether you’re traveling with kids or planning a quiet couples’ retreat, this place has you covered

Address: The Newport Resort, 7888 Church St, Egg Harbor, WI 54209

The Newport Resort is your cozy home base for exploring Door County—book your stay today and start planning your Wisconsin adventure!

Location: Milwaukee, Wisconsin

If you're after a cozy, affordable Milwaukee getaway with vintage vibes and modern perks, The Knickerbocker on the Lake is a perfect pick. This restored boutique hotel blends period charm with city convenience—right in the heart of downtown and just a short walk from museums, theaters, and top-rated restaurants.

• Classic Charm Meets Comfort – Stay in one of 160 rooms or suites featuring elegant period furniture and updated amenities
• Walkable Location – Easily explore downtown Milwaukee’s attractions, from local dining to cultural hotspots
• Lake Views Available – Upgrade to a suite with views of Lake Michigan for something extra special
• On-Site Spa – Relax at the full-service Knick Salon and Spa with massages, facials, and rejuvenating treatments
• 24-Hour Fitness Center – Keep your wellness routine going anytime that works for you
• Special Event Space – Host your next gathering in the elegant Juneau Room, perfect for weddings or celebrations
• Extra Conveniences – Enjoy custom tailoring, valet dry cleaning, and fully equipped kitchenettes in every room
• Delicious Dining – Grab a seat at The Knick Restaurant for upscale meals and a must-try weekend brunch

Address: The Knickerbocker on the Lake, 1028 E Juneau Ave, Milwaukee, WI 53202

The Knickerbocker on the Lake offers old-school charm and downtown access at a great value—book your stay and enjoy a laid-back Milwaukee getaway!

Location: Elsah, Illinois

Looking for a peaceful getaway tucked into a charming historic town? The Green Tree Inn in Elsah is a hidden gem nestled in a quiet valley surrounded by natural beauty. With just five cozy rooms and warm, personalized touches, it’s the kind of place where time slows down—and that's exactly the point.

• Charming Atmosphere – Located in historic Elsah, this intimate inn offers scenic valley views and serious small-town charm
• Cozy Accommodations – Choose from five uniquely decorated rooms with private baths and a relaxing ambiance; most feature queen beds
• Comfortable Amenities – Enjoy in-room A/C, TVs in most rooms, and access to a communal satellite TV setup
• Stay Connected – Free Wi-Fi is available throughout the property
• Relaxing Common Spaces – Spend time in the antique-filled gathering room, unwind by the fireplace, or take in the views from the scenic deck
• Extra Perks – Play a board game, borrow a bike, or treat yourself to an in-room massage for extra relaxation
• Delicious Touches – Help yourself to homemade snacks, hot beverages, and a stocked fridge with water and soda
• Homemade Meals – Wake up to a fresh, homemade breakfast—and if you'd like, request a home-cooked evening meal, too

Address: The Green Tree Inn, 15 Mill St., Elsah, IL 62028
Phone: 618-374-2821

The Green Tree Inn is the perfect place to slow down, unwind, and soak in the beauty of historic Elsah—book your stay and feel right at home.

Location: Kohler, Wisconsin

Looking for a luxury resort escape within driving distance of Chicago? The American Club, Kohler is a top-tier destination that blends historic charm, five-star comfort, and all-season activities. Just 2.5 hours from the city, this iconic resort is perfect for couples, families, or anyone craving a rejuvenating getaway—with options to suit both splurge-worthy retreats and budget-friendly stays.

• Two Ways to Stay – Choose between the luxurious American Club or the more affordable yet still elegant Inn on Woodlake
• Summer Fun – Enjoy golf, hiking trails, and poolside relaxation—plus family-friendly activities and romantic packages
• Winter Wellness – Cozy up by the fire, unwind in the spa, or swim in the heated indoor pools
• All-Inclusive Packages – From couples’ getaways to golf weekends and family vacations, there’s a package for everyone—including women-specific golf programs
• Signature Spa – Kohler Waters Spa features a rooftop deck with whirlpool and fireplace, plus hydrotherapy, massages, and luxury treatments
• Romantic Spa Experiences – Book the newly renovated couples’ suite for a side-by-side massage and spa day for two
• Fitness & Wellness – Take yoga classes at Yoga on the Lake or stay active with cutting-edge fitness facilities and outdoor adventures
• Easy Getaway – Located in Kohler, Wisconsin, just 2.5 hours north of Chicago—ideal for weekend escapes

Address: The American Club, Kohler, 419 Highland Dr, Kohler, WI 53044
Phone: 800-344-2838

The American Club, Kohler delivers relaxation, recreation, and romance all in one unforgettable resort—book now and treat yourself to the getaway you deserve.

Location: Cedarburg, Wisconsin

For a cozy weekend escape just north of Chicago, the Washington House Inn in charming Cedarburg is a perfect pick. Set inside a beautifully restored historic building, this boutique inn blends timeless character with modern comforts—plus it's just steps from one of Wisconsin’s most walkable and welcoming downtowns.

• Charming Historic Stay – Located in a 19th-century building, this inn features stylish rooms full of warmth and character
• Cozy Perks – Enjoy complimentary high-speed Wi-Fi and a wine and cheese social hour every afternoon
• Explore Main Street – Cedarburg’s Main Street is filled with 70+ boutiques, sweet shops, and local eateries—great for strolling and snacking
• Nearby Museums – Dive into local history at the General Store Museum, Kuhefuss House Museum, or the Wisconsin Museum of Quilts and Fiber Arts
• Easy Escape – Just 110 miles north of Chicago, Cedarburg is an ideal getaway that feels a world away

Address: Washington House Inn, W62 N573 Washington Ave, Cedarburg, WI 53012
Phone: 262-375-3550

Washington House Inn is ready to welcome you with small-town charm and big-time relaxation—book your stay and unwind in beautiful Cedarburg.