← The Weekend Getaways
🏛️ CulturalDay trip · from Chicago, IL

Vineyard Sunsets & Tasting Rooms

Experience world-class wines and breathtaking vineyard vistas while savoring intimate tastings in charming Illinois wine country.

Day 1 — Sable Creek Winery
Day 1Sable Creek Winery

Day 1Sable Creek Winery

🚗 2 hr 22 min driving📍 4 stops
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Morning
🚗
Drive
Chicago, ILSable Creek Winery
46 min8:00 AM8:46 AM
Sable Creek Winery
Sable Creek Winery
4.8
Discover award-winning wines and scenic vineyard views just an hour from Chicago, offering a sophisticated escape into Illinois wine country.
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Lunch
Inzo Italian Kitchen — Joliet, IL
Inzo Italian Kitchen — Joliet, IL
4.4
A solid local Italian spot in Joliet — fresh pasta and wood-fired plates in a relaxed setting. A good lunch stop between the winery and the afternoon at Old Joliet Prison, and a different register from the evening diner stop.
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Afternoon
🚗
Drive
Sable Creek WineryOld Joliet Prison
19 min12:00 PM12:19 PM
Old Joliet Prison
Old Joliet Prison
4.6
Tour the Gothic-style cellblocks and learn the stories of famous inmates through guided walks across the historic grounds. Explore the imposing Stone Quarry and visit the restored dining hall while imagining life behind the 40-foot walls that once housed Al Capone.
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Evening
🚗
Drive
Old Joliet PrisonPortillo's Shorewood
23 min5:00 PM5:23 PM
Merichka's — Crest Hill, IL
Merichka's — Crest Hill, IL
4.5
A Will County institution since 1933 — unpretentious booths, legendary broasted chicken, and the kind of old-school atmosphere that pairs perfectly with a day spent at an abandoned prison. Cash only adds to the charm.
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Drive
Portillo's ShorewoodChicago, IL
54 min6:23 PM7:17 PM
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