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Windings to Unwind

Connecting Midwesterners to a world full of road-trips, hikes, nature and adventure

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  • Naperville Day Trips (18)
  • Hiking Near Chicago (16)
  • Weekend Getaways (16)
  • Long Trips (15)
  • Biking Near Chicago (11)

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  • Scenic Hikes (21)
  • Hiking Near Chicago (19)
  • Summer Picnic (18)
  • Biking Near Chicago (16)
  • Boating (11)

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Recent Posts

  • Road Trip from Chicago during historic Winter Storm
  • Road Trip from Chicago to Pensacola and Florida panhandle
  • Best Chicago Road Trip Memories of 2022
  • Disney World Lightning Lanes + Tips and Park Planning Strategy
  • Chicago to Florida Road Trip – Disney and Key West
  • Road Trip from Chicago to New Orleans
  • Best Winter Road Trips from Chicago
  • Best of Chicago Fall – 2022
  • Road Trip from Chicago to Kentucky Bourbon Trail
  • Hiking at Maple Grove, Downers Grove

Category: Long Trips

Road Trip from Chicago during historic Winter Storm
Long Trips, Winter Road Trips

Road Trip from Chicago during historic Winter Storm

Guess who chose to crash our winter road trip? The December 2022 North American Winter Storm! Here goes the chronicles of Chicago to Pensacola road trip amidst the menacing winter snow storm of 2022. Continue reading Road Trip from Chicago during historic Winter Storm

Road Trip from Chicago to Pensacola and Florida panhandle
Historical Towns, Long Trips, Winter Road Trips

Road Trip from Chicago to Pensacola and Florida panhandle

Florida panhandle a.k.a. Emerald Coast is a perfect all-season beach getaway for those longing for pristine white-sand, emerald waters and an unforgettable 14-hour Florida road trip from Chicago. Continue reading Road Trip from Chicago to Pensacola and Florida panhandle

Chicago to Florida Road Trip – Disney and Key West
Long Trips, National Parks, Winter Road Trips

Chicago to Florida Road Trip – Disney and Key West

An epic 7-day, 1500-mile winter road trip from Chicago to Florida –
Wetlands and gators at Everglades National Park, NASA Kennedy Space Center at Cape Canaveral, white sand beaches, historical forts and many water adventures at Key West. Continue reading Chicago to Florida Road Trip – Disney and Key West

Road Trip from Chicago to New Orleans
Historical Towns, Long Trips, Winter Road Trips

Road Trip from Chicago to New Orleans

From Brr! to tan lines – A memorable family winter road trip from Chicago to New Orleans, Louisiana. Continue reading Road Trip from Chicago to New Orleans

Best Winter Road Trips from Chicago
Historical Towns, Long Trips, Winter Road Trips

Best Winter Road Trips from Chicago

Chicago winter escapades – narrating the best road trips from Chicago with detailed itineraries and pictures. Continue reading Best Winter Road Trips from Chicago

Road Trip from Chicago to Chattanooga
Adventure Trips, Historical Towns, Long Trips, Spring Break Trips, Summer Road Trips

Road Trip from Chicago to Chattanooga

From chilly to chilling – a memorable spring break road trip from Chicago to Chattanooga. Continue reading Road Trip from Chicago to Chattanooga

Road Trip from Chicago to Red River Gorge, Kentucky
Adventure Trips, Fall Color Destinations, Long Trips, Summer Road Trips

Road Trip from Chicago to Red River Gorge, Kentucky

Summer Adventure road-trip from Chicago to Red River Gorge and Cumberland Falls, Kentucky Continue reading Road Trip from Chicago to Red River Gorge, Kentucky

“No-Regrets – 2022” – Rafting Adventure Road Trip from Chicago to New River Gorge, West Virginia
Adventure Trips, Boys Trip - No-Regrets, Long Trips

“No-Regrets – 2022” – Rafting Adventure Road Trip from Chicago to New River Gorge, West Virginia

No Regrets 2022 – White-water rafting adventure road-trip from Chicago to West Virginia Continue reading “No-Regrets – 2022” – Rafting Adventure Road Trip from Chicago to New River Gorge, West Virginia

9 Summer Road Trip Ideas from Chicago With Detailed Itineraries
Adventure Trips, Long Trips, National Parks, Weekend Getaways

9 Summer Road Trip Ideas from Chicago With Detailed Itineraries

9 curated summer road trip ideas for the best vacation with family or friends. Continue reading 9 Summer Road Trip Ideas from Chicago With Detailed Itineraries

Best Spring Break Road Trips from Chicago
Long Trips, Spring Break Trips, Weekend Getaways

Best Spring Break Road Trips from Chicago

Chicago Spring Break Roadtrip Ideas Continue reading Best Spring Break Road Trips from Chicago

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