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Windings to Unwind

Chronicling Chicago's best road trips, hiking and biking trails

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  • Best Spring Break Road Trips from Chicago
  • Spring Break Road Trip from Chicago to Cherry Blossom Festival, Washington D.C.
  • Spring Weekend Road Trip to Put-In-Bay, Ohio
  • Spring Break Road Trip from Chicago to St Louis, Springfield and Meramec Caverns
  • Spring Break Road Trip from Chicago to Hot Springs National Park, Arkansas
  • Summer Day Trip to Galena
  • Summer Camping Trip at Devil’s Lake State Park, Wisconsin
  • Biking and Picnic at Blackwell Forest Preserve
  • Summer Weekend Road Trip from Chicago to Cuyahoga National Park, Ohio.
  • Summer Biking at Lake Renwick Preserve, Plainfield
  • Summer Picnic at Herrick Lake Forest Preserve, Wheaton

Social Navigation

  • Best Spring Break Road Trips from Chicago
  • Spring Break Road Trip from Chicago to Cherry Blossom Festival, Washington D.C.
  • Spring Weekend Road Trip to Put-In-Bay, Ohio
  • Spring Break Road Trip from Chicago to St Louis, Springfield and Meramec Caverns
  • Spring Break Road Trip from Chicago to Hot Springs National Park, Arkansas
  • Summer Day Trip to Galena
  • Summer Camping Trip at Devil’s Lake State Park, Wisconsin
  • Biking and Picnic at Blackwell Forest Preserve
  • Summer Weekend Road Trip from Chicago to Cuyahoga National Park, Ohio.
  • Summer Biking at Lake Renwick Preserve, Plainfield
  • Summer Picnic at Herrick Lake Forest Preserve, Wheaton

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Recent Posts

  • “No-Regrets – 2022” – Rafting Adventure Road Trip from Chicago to New River Gorge, West Virginia
  • How to plan a memorable road trip?
  • Best Summer Road Trips from Chicago
  • “No-Regrets – 2021” – Rafting Road-Trip from Chicago to Niagara, Wisconsin
  • Best Spring Break Road Trips from Chicago
  • Biking at Fox River Trail – North Aurora to Batavia
  • Road Trip from Chicago to The Great Smoky Mountains
  • Camping Trip to Ozark Scenic Riverways, Missouri
  • Spring Break Road Trip from Chicago to Hot Springs National Park, Arkansas
  • Spring Break Road Trip from Chicago to St Louis, Springfield and Meramec Caverns

Category: Weekend Chicago Getaways

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

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

Best Summer Road Trips from Chicago
Adventure Trips, Long Trips, National Parks, Weekend Chicago Getaways

Best Summer Road Trips from Chicago

Chicago summer and road-trips, equally yoked! Continue reading Best Summer Road Trips from Chicago

“No-Regrets – 2021” – Rafting Road-Trip from Chicago to Niagara, Wisconsin
Adventure Trips, Boys Trip - No-Regrets, Weekend Chicago Getaways

“No-Regrets – 2021” – Rafting Road-Trip from Chicago to Niagara, Wisconsin

No Regrets 2021 – White-water rafting adventure road-trip from Chicago Continue reading “No-Regrets – 2021” – Rafting Road-Trip from Chicago to Niagara, Wisconsin

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

Best Spring Break Road Trips from Chicago

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

Road Trip from Chicago to The Great Smoky Mountains
Adventure Trips, Fall Color Destinations, Long Trips, National Parks, Weekend Chicago Getaways

Road Trip from Chicago to The Great Smoky Mountains

Road Trip from Chicago to The Smokey Mountains National Park Continue reading Road Trip from Chicago to The Great Smoky Mountains

Camping Trip to Ozark Scenic Riverways, Missouri
Weekend Chicago Getaways

Camping Trip to Ozark Scenic Riverways, Missouri

A camping trip at the bank of Jacks Fork river, part of Ozark Scenic Riverways. Continue reading Camping Trip to Ozark Scenic Riverways, Missouri

Spring Break Road Trip from Chicago to St Louis, Springfield and Meramec Caverns
Spring Break Trips, Weekend Chicago Getaways

Spring Break Road Trip from Chicago to St Louis, Springfield and Meramec Caverns

Spring Break Road Trip from Chicago to Springfield and St Louis Continue reading Spring Break Road Trip from Chicago to St Louis, Springfield and Meramec Caverns

“No-Regrets 2020” – All Boys Camping Trip to Iowa
Boys Trip - No-Regrets, Weekend Chicago Getaways

“No-Regrets 2020” – All Boys Camping Trip to Iowa

No-Regrets 2020 – All boys camping trip from Chicago to Iowa Continue reading “No-Regrets 2020” – All Boys Camping Trip to Iowa

Summer Camping Trip at Devil’s Lake State Park, Wisconsin
Weekend Chicago Getaways

Summer Camping Trip at Devil’s Lake State Park, Wisconsin

Why Devil’s Lake? One of the closest state park for Chicagoans which is a complete package in itself – be … Continue reading Summer Camping Trip at Devil’s Lake State Park, Wisconsin

Summer Weekend Road Trip from Chicago to Cuyahoga National Park, Ohio.
National Parks, Weekend Chicago Getaways

Summer Weekend Road Trip from Chicago to Cuyahoga National Park, Ohio.

Why Cuyahoga? One of the closest National Park from Chicago. Scenic train ride is a rare experience and highly recommended … Continue reading Summer Weekend Road Trip from Chicago to Cuyahoga National Park, Ohio.

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