← The Weekend Getaways
🌿 RelaxedWeekend · from Chicago, IL

Alpine Waters & Lakeside Serenity

Escape to Wisconsin's pristine lakes for a weekend of waterside tranquility, charming towns, and rejuvenating spa culture away from the city.

Day 1 — Lake GenevaDay 2 — Elkhart Lake
Day 1Lake Geneva

Day 1Lake Geneva

🚗 2 hr 24 min driving📍 5 stops
🌅
Morning
🚗
Drive
Chicago, ILLake Geneva
1 hr 28 min8:00 AM9:28 AM
Lake Geneva
Lake Geneva
A Victorian lakeside resort town on the shores of Geneva Lake with grand spas, paddle-wheel cruises, upscale restaurants, and an unhurried waterfront promenade lined with boutique shops and wine bars.
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Lunch
🍽️ Lunch10:28 AM
Oakfire
Oakfire
A wood-fired pizzeria near Lake County, IL with quality ingredients and technique that stands out from the usual suburban options.
4.4Pizza Restaurant📍 Maps →
4 options · tap to switch
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Afternoon
🚗
Drive
Lake GenevaStaller Estate Winery & Distillery
28 min12:00 PM12:28 PM
Staller Estate Winery & Distillery
Staller Estate Winery & Distillery
4.7
Taste small-batch wines and craft spirits while overlooking vineyard rows, then explore the tasting room's curated flight selections. Sip seasonal varietals and learn distilling techniques from knowledgeable staff in this intimate setting.
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Evening
🚗
Drive
Staller Estate Winery & DistilleryTuscan Tavern & Grill
28 min5:00 PM5:28 PM
🍽️ Dinner5:28 PM
Tuscan Tavern & Grill
Tuscan Tavern & Grill
Immerse yourself in rustic Italian charm and warm hospitality while enjoying hearty, comforting cuisine that transports you to the countryside.
4.4Italian Restaurant📍 Maps →
4 options · tap to switch
🛏️
Destination Geneva National
A sprawling lakeside resort community on the shores of Lake Geneva — golf, spa, lake access, and villa-style accommodations that give you space to spread out. The go-to choice for a quieter Lake Geneva weekend away from the packed downtown waterfront.
Day 2Lake Geneva

Day 2Lake Geneva

🚗 1 hr 58 min driving📍 3 stops
🌅
Morning
🚗
Drive
Lake GenevaYerkes Observatory
10 min8:00 AM8:10 AM
Yerkes Observatory
Yerkes Observatory
4.8
Explore the University of Chicago's historic Yerkes Observatory in Williams Bay, home to the world's largest refracting telescope. The Romanesque Revival building and its 40-inch telescope dome are open for tours, offering a fascinating window into late 19th-century astronomical science on the shores of Geneva Lake.
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Lunch
🚗
Drive
Yerkes ObservatoryLake Geneva Shoreline
10 min9:10 AM9:20 AM
Lake Geneva Shoreline
Lake Geneva Shoreline
4.8
Stroll the 21-mile Geneva Lake Shore Path, one of the oldest continuously used footpaths in Wisconsin. The lakeside walk winds past Victorian-era estates and gardens, with sweeping views of the shimmering lake and a relaxed pace that embodies the Lake Geneva spirit.
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Afternoon
🚗
Drive
Lake Geneva ShorelineAbbey Springs Resort Area
8 min12:00 PM12:08 PM
Abbey Springs Resort Area
Abbey Springs Resort Area
4.6
Wind down at the Abbey Springs lakefront on Fontana Bay, where you can walk peaceful shoreside trails, enjoy the marina views, and browse the resort's relaxed waterfront setting. The surrounding neighborhood of quiet roads and lake glimpses makes for a perfect leisurely afternoon stroll before heading home.
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Evening
🚗
Drive
Abbey Springs Resort AreaChicago, IL
1 hr 30 min5:00 PM6:30 PM
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