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Windings to Unwind

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

Categories

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

Tags

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

Year

  • 2023 (91)
  • 2022 (197)
  • 2021 (10)
  • 2020 (82)
  • 2019 (32)

Categories

  • Adventure Trips
  • Biking Near Chicago
  • Biking Road Trips
  • Boys Trip – No-Regrets
  • Fall Color Destinations
  • Hiking Near Chicago
  • Historical Towns
  • How-to Guides
  • Long Trips
  • Naperville Day Trips
  • National Parks
  • Spring Break Trips
  • Summer Road Trips
  • Trips with Young Kids
  • Weekend Getaways
  • Winter Road Trips
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Activities for Young Kids ATV Ride Beaches Biking Near Chicago Biking Road Trips Bird Watching Boating Camping Christmas-Trip Cliff Jumping Fall Fall Color Hikes Fall Colors Fishing guys trip Hiking Hiking Near Chicago Kayaking Kids Nature Center Mountain Biking National Park Ohio Pontoon Boating Pontoon Rentals River Tubing Road-Trip Roadtrip Rock Climbing Scenic Bridges Scenic Hikes Scenic Overlook Scenic Roads Scenic Train Scenic Watch Tower Sculpture Park Sledding Around Naperville Snow Storm Summer Picnic Swimming Hole Touristy Downtown Travel Underground Caverns Waterfalls White water rafting Winter Trip Ziplining

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: National Parks

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

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

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

Spring Break Road Trip from Chicago to Hot Springs National Park, Arkansas
Biking Road Trips, Long Trips, National Parks, Spring Break Trips, Summer Road Trips

Spring Break Road Trip from Chicago to Hot Springs National Park, Arkansas

A Spring Break Road Trip to Hot Springs Arkansas to nix the winter cabin fever for Chicago folks. Continue reading Spring Break Road Trip from Chicago to Hot Springs National Park, Arkansas

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

“No-Regrets 2019” – All Boys Road Trip from Chicago to Rocky Mountains National Park and Colorado Springs, Colorado
Adventure Trips, Boys Trip - No-Regrets, Long Trips, National Parks

“No-Regrets 2019” – All Boys Road Trip from Chicago to Rocky Mountains National Park and Colorado Springs, Colorado

What is No-Regrets A mancation, a tradition, where bunch of close friends hunker down for a weekend of adventure, each … Continue reading “No-Regrets 2019” – All Boys Road Trip from Chicago to Rocky Mountains National Park and Colorado Springs, Colorado

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