• January 1, 2025 - Updated with new information since originally published.
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  • Our editors recommend these diverse local experiences.

1. Book a room at Grand Geneva Resort - 1 hour 30 minutes from Chicago

Category: Unique Accommodations
© Grand Geneva Resort

2. Take the kids to Grand Traverse Resort - 5 hours from Chicago

Category: Unique Accommodations
© Grand Traverse Resort

3. Swim in the pool at The Abbey Resort - 1 hour 40 minutes

Category: Unique Accommodations

4. Head to the beach in Egg Harbor at The Newport Resort - 4 hours 30 minutes

Category: Unique Accommodations
© The Newport Resort

5. The Knickerbocker on the Lake - 1 hour 30 minute

Category: Weekend Activities & Fun Outdoors
© The Knickerbocker on the Lake

6. The Green Tree Inn - 4 hours 25 min

Category: Unique Accommodations
© The Green Tree Inn

7. The American Club, Kohler - 2 hours 30 minutes

© The American Club, Kohler

8. Washington House Inn - 2 hours

Category: Unique Accommodations
© Washington House Inn

9. Sweethaven Resort - 1 hour 20 minutes from Chicago

Category: Unique Accommodations

10. Hawk Valley Retreat & Cottages - 2 hours and 45 minutes

© Hawk Valley Retreat & Cottages

11. Mansion Hill Inn for Couples - 2 hours 30 minutes

Category: Unique Accommodations

12. Vrooman Mansion - 2 hours

Category: Museums & Culture for Couples

13. Oakwood Resort, Syracuse, IN

Category: Unique Accommodations
© Dariusz Jarzabek/stock.adobe.com

14. Saugatuck

© sstevens3/stock.adobe.com

15. Farmers Guest House - 2 hours 45 minutes

Category: Weekend Activities & Fun Outdoors
© Farmers Guest House

Summary and Frequenly Asked Questions:

Get away from Chicago for a weekend of swimming in indoor & outdoor pools, relaxing at a spa, skiing, a game of golf, boutique shopping and museums. Many nearby hotels, resorts and romantic inns offer affordable room rates and seasonal packages. Whether you are looking to relax on the beach, hike, bike, or go on a fun shopping trip, there is plenty to choose from.

Driving Distances from Chicago

From Chicago To     Driving Time
Lake Geneva, WI1 hour and 30 minutes
Galena, IL2 hours 45 minutes
Kohler, WI2 hours and 20 minutes
Chesterton, Indiana1 hour
Madison, WI2 hours and 30 minutes
Cedarburg, WI2 hours
Acme, MI5 hours
Bloomingdale, IL40 minutes
Preemption,2 hours and 45 minutes
Rockton1 hour 35 minutes
Oak Park, IL15 min
Springfield, IL3 hours
Henry2 hours
Mt. Vernon, IL4 hours
Taylorville3 hours
Paxton, IL1 hour 45 minutes
West Dundee, IL50 minutes

Plan Your Trip

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