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Windings to Unwind

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

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  • Biking Near Chicago (11)

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

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  • 2023 (91)
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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
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

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 Kentucky Bourbon Trail
Boys Trip - No-Regrets, Weekend Getaways, Winter Road Trips

Road Trip from Chicago to Kentucky Bourbon Trail

Ready for an unforgettable weekend road trip to the Bourbon Capital of the World? Continue reading Road Trip from Chicago to Kentucky Bourbon Trail

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

Best Chicago Road Trip Memories of  2022
Adventure Trips, Spring Break Trips, Summer Road Trips, Winter Road Trips

Best Chicago Road Trip Memories of 2022

As we head into the last hours of 2022, here are the best pictures taken al fresco during my numerous … Continue reading Best Chicago Road Trip Memories of 2022

Disney World Lightning Lanes + Tips and Park Planning Strategy
How-to Guides

Disney World Lightning Lanes + Tips and Park Planning Strategy

Like the magic and mystique of Disney World but hate waiting in lines?Looking for the lowdown on the best Disney … Continue reading Disney World Lightning Lanes + Tips and Park Planning Strategy

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 of Chicago Fall – 2022
Hiking Near Chicago

Best of Chicago Fall – 2022

Curious to see a medley of best fall colors around Chicago area? Continue reading Best of Chicago Fall – 2022

Hiking at Maple Grove, Downers Grove
Biking Near Chicago, Fall Color Destinations, Hiking Near Chicago, Naperville Day Trips

Hiking at Maple Grove, Downers Grove

Take an easy-paced 1.5-mile hike through the ancient maple grove to swat your worries and stress away. Continue reading Hiking at Maple Grove, Downers Grove

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