Road Trips from Chicago

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Lakefront Trail & Public Market

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Chicago → Evanston → Waukegan → Kenosha → Racine → Milwaukee

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15 miles of Lake Michigan shore & dunes

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Chicago → Hammond → Gary → Portage → Indiana Dunes Visitor Center

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18 canyons & scenic waterfall hikes

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Chicago → Joliet → Morris → Ottawa → Starved Rock State Park

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Shore path & charming lakefront town

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Chicago → Gurnee → Kenosha → Pleasant Prairie → Lake Geneva

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Wisconsin State Capitol & lakeside biking

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Chicago → Schaumburg → Elgin → Rockford → Janesville → Madison

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Lake Michigan beach town escape

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Chicago → Hammond → Gary → Michigan City → New Buffalo

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Anderson Japanese Gardens & Burpee Museum

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Chicago → Rosemont → Des Plaines → Schaumburg → Elgin → Rockford

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Trails & river views near Chicago

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Chicago → Tinley Park → Matteson → Manteno → Bourbonnais → Kankakee River State Park

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Gateway Arch & BBQ

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Chicago → Bolingbrook → Dwight → Bloomington-Normal → Lincoln → Springfield → Litchfield → St. Louis

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300 miles of shoreline & 5 state parks

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Chicago → Milwaukee → Port Washington → Sheboygan → Manitowoc → Green Bay → WI-57 → Sturgeon Bay

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Skyline Chili & riverfront walks

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Chicago → Indianapolis → Greensburg → Cincinnati

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Indy 500 Museum & canal walk

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Chicago → Merrillville → Rensselaer → Lafayette → Indianapolis

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Art galleries, dunes & beaches

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Chicago → Gary → Michigan City → Benton Harbor → South Haven → Saugatuck

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Sandstone river tours & water-park fun

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Chicago → Rockford → Madison → Baraboo → Wisconsin Dells

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Tulip Time Festival & sandy beaches

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Chicago → Gary → Michigan City → Benton Harbor → South Haven → Holland

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19th-century Main Street & rolling bluffs

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Chicago → Elgin → Rockford → Freeport → Galena

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Lincoln Presidential Library & historic sites

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Chicago → Bolingbrook → Bloomington-Normal → Lincoln → Springfield

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Sleeping Bear Dunes & wineries

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Chicago → Gary → Michigan City → Grand Rapids → Cadillac → Traverse City

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Motown Museum & auto heritage

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Chicago → Gary → Michigan City → Benton Harbor → Ann Arbor → Detroit

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Rock & Roll Hall of Fame

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Chicago → South Bend → Toledo → Sandusky → Cleveland

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Old Market & Henry Doorly Zoo

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Chicago → Rockford → Dubuque → Cedar Rapids → Des Moines → Omaha

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Garden of the Gods & hiking trails

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Chicago → Kankakee → Effingham → Mt. Vernon → Carbondale → Shawnee National Forest

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Ash Cave & Old Man’s Cave trails

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Chicago → Indianapolis → Dayton → Columbus → Logan → Hocking Hills State Park

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Mississippi riverfront & twin-city culture

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Chicago → Rockford → Madison → La Crosse → Rochester → Minneapolis

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American & Horseshoe Falls viewpoints

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Chicago → Toledo → Cleveland → Erie → Buffalo → Niagara Falls

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Cades Cove, Newfound Gap, Clingmans Dome

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Chicago → Indianapolis → Louisville → Lexington → Knoxville → Great Smoky Mountains National Park

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Mt Rushmore, Needles Hwy, Custer SP

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Chicago → Madison → La Crosse → Rochester → Sioux Falls → Rapid City → Badlands National Park

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469-mile parkway & scenic overlooks

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Chicago → Indianapolis → Louisville → Lexington → Roanoke → Asheville → Blue Ridge Parkway

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Duluth to Grand Portage Lake Superior coast

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Chicago → Madison → Eau Claire → Duluth → Two Harbors → Silver Bay → Grand Marais

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Sea caves, lighthouses & kayaking tours

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Chicago → Rockford → Madison → Eau Claire → Ashland → Bayfield → Apostle Islands National Lakeshore

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Horse-drawn carriages & Great Lakes charm

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Chicago → Gary → Grand Rapids → Traverse City → Mackinaw City → Mackinac Island Ferry Dock

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Three Rivers & Duquesne Incline

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Chicago → Toledo → Cleveland → Akron → Pittsburgh

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Jazz district & BBQ trails

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Chicago → Bloomington → Springfield (IL) → St. Louis → Columbia → Kansas City

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Broadway live music & BBQ

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Chicago → Kankakee → Champaign → Effingham → Paducah → Clarksville → Nashville

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Branson, Ozark National Scenic Riverways

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Chicago → Springfield (IL) → St. Louis → Rolla → Springfield (MO) → Branson → Ozark Mountains

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Mother Road route to St. Louis

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Chicago → Joliet → Dwight → Pontiac → Bloomington → Springfield → Litchfield → St. Louis

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Graceland & Beale Street

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Chicago → Kankakee → Champaign → Effingham → Cairo → Memphis

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Falls Park & downtown walks

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Chicago → Rockford → Madison → La Crosse → Rochester → Sioux Falls

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State Capitol & college town energy

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Chicago → Rockford → Dubuque → Cedar Rapids → Des Moines → Lincoln

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Trail Ridge Road & alpine lakes

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Chicago → Des Moines → Omaha → Lincoln → Kearney → Denver → Estes Park → Rocky Mountain National Park

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Times Square, Central Park & skyline

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Chicago → Toledo → Cleveland → Pittsburgh → Harrisburg → Philadelphia → New York City

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Rainbow Row & southern cuisine

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Chicago → Indianapolis → Lexington → Knoxville → Asheville → Columbia → Charleston

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French Quarter & jazz nightlife

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Chicago → Memphis → Jackson (MS) → New Orleans

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Rocky Mountain gateway city

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Chicago → Davenport → Des Moines → Lincoln → Denver

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Spanish moss & historic squares

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Chicago → Indianapolis → Louisville → Nashville → Atlanta → Savannah

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Iconic butte & starry skies

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Chicago → Madison → La Crosse → Sioux Falls → Rapid City → Sundance → Devils Tower National Monument

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National Mall & Smithsonian museums

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Chicago → Toledo → Cleveland → Pittsburgh → Hagerstown → Washington D.C.

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Tahquamenon Falls & Keweenaw Peninsula

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Chicago → Green Bay → Menominee → Escanaba → Munising → Tahquamenon Falls → Upper Peninsula Waterfalls Loop

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Liberty Bell & cheesesteaks

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Chicago → Toledo → Cleveland → Pittsburgh → Harrisburg → Philadelphia

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Tallest dunes in North America

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Chicago → Des Moines → Lincoln → Colorado Springs → Alamosa → Great Sand Dunes National Park

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Live music, BBQ & Barton Springs

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Chicago → Springfield (IL) → St. Louis → Little Rock → Texarkana → Dallas → Austin

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Lake Placid & fall foliage

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Chicago → Toledo → Cleveland → Buffalo → Rochester → Syracuse → Lake George → Adirondack Mountains

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Remote Lake Superior island adventure

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Chicago → Milwaukee → Green Bay → Houghton → Copper Harbor → Isle Royale Ferry Dock

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NASA Space Center & culinary scene

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Chicago → St. Louis → Memphis → Jackson (MS) → Baton Rouge → Houston

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Thermal baths & historic spa town

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Chicago → St. Louis → Little Rock → Hot Springs National Park

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Old Faithful, Grand Canyon of Yellowstone

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Chicago → Madison → La Crosse → Sioux Falls → Rapid City → Buffalo (WY) → Cody → Yellowstone National Park

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Jenny Lake & Teton Range views

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Chicago → Des Moines → Omaha → Cheyenne → Rock Springs → Jackson → Grand Teton National Park

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Cadillac Mountain & coastal hikes

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Chicago → Cleveland → Buffalo → Albany → Portland (ME) → Bangor → Bar Harbor → Acadia National Park

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Narrows, Angels Landing & red-rock cliffs

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Chicago → Kansas City → Denver → Glenwood Springs → Moab → St. George → Zion National Park

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Blue Ridge + Skyline Drive combo

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Chicago → Indianapolis → Louisville → Knoxville → Asheville → Boone → Roanoke → Appalachian Mountains Scenic Drive

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Full loop around Lake Superior

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Chicago → Milwaukee → Green Bay → Marquette → Houghton → Thunder Bay → Duluth → Bayfield → Chicago

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Moab base for Arches & Canyonlands

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Chicago → Kansas City → Denver → Grand Junction → Moab → Arches National Park → Canyonlands National Park → Moab

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Amphitheater hoodoos & sunrise views

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Chicago → Kansas City → Denver → Glenwood Springs → Moab → Bryce Canyon National Park

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Follow Mississippi River through 10 states

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Chicago → Springfield (IL) → St. Louis → Memphis → Vicksburg → Baton Rouge → New Orleans

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Delicate Arch & red desert formations

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Chicago → Kansas City → Denver → Glenwood Springs → Grand Junction → Moab → Arches National Park

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Asheville to Charleston scenic loop

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Chicago → Louisville → Knoxville → Gatlinburg → Asheville → Greenville → Charleston → Columbia → Knoxville → Chicago

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Mesa Arch & Island-in-the-Sky

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Chicago → Kansas City → Denver → Grand Junction → Moab → Canyonlands National Park

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Freedom Trail & harbor views

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Chicago → Cleveland → Buffalo → Albany → Worcester → Boston

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Adobe plaza & desert landscapes

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Chicago → Kansas City → Wichita → Amarillo → Santa Fe

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Fruita orchards & red-rock domes

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Chicago → Kansas City → Denver → Grand Junction → Hanksville → Capitol Reef National Park

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Overseas Highway to Key West

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Chicago → Nashville → Atlanta → Orlando → Miami → Key Largo → Key West

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Highway 1 & Big Sur coastline

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Chicago → Denver → Las Vegas → Los Angeles → Santa Barbara → Monterey → San Francisco

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Golden Gate Bridge & Pacific views

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Chicago → Omaha → Denver → Salt Lake City → Reno → San Francisco

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Clearwater, Sarasota, Naples & Keys

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Chicago → Nashville → Birmingham → Mobile → Pensacola → Tampa → Naples

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Mount Rainier, Pike Place & coastal drive

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Chicago → Minneapolis → Fargo → Billings → Spokane → Seattle

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Deep blue volcanic lake vistas

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Chicago → Omaha → Denver → Salt Lake City → Bend → Crater Lake National Park

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Columbia River Gorge & Oregon Coast

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Chicago → Des Moines → Omaha → Boise → Pendleton → Portland

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South Rim viewpoints & scenic drives

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Chicago → Kansas City → Denver → Flagstaff → Grand Canyon National Park

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Remote North Rim vistas

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Chicago → Kansas City → Denver → Moab → Page → Kanab → Grand Canyon North Rim

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Strip, Hoover Dam & Red Rock Canyon

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Chicago → Kansas City → Denver → Grand Junction → St. George → Las Vegas

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Airboats & alligators near Miami

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Chicago → Nashville → Atlanta → Orlando → Miami → Homestead → Everglades National Park

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Badwater Basin & Zabriskie Point

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Chicago → Kansas City → Denver → Grand Junction → Las Vegas → Pahrump → Death Valley National Park

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Full Mother Road Chicago to Santa Monica

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Chicago → Joliet → Springfield (IL) → St. Louis → Tulsa → Oklahoma City → Amarillo → Albuquerque → Flagstaff → Kingman → Barstow → Santa Monica

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Glacier→Seattle→Olympic→Portland

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Chicago → Minneapolis → Billings → Spokane → Seattle → Portland → Boise → Missoula → Chicago

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All five Great Lakes drive

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Chicago → Milwaukee → Green Bay → Marquette → Sault Ste. Marie → Toronto → Niagara Falls → Cleveland → Toledo → Chicago

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Yosemite Valley, Half Dome & waterfalls

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Chicago → Denver → Salt Lake City → Reno → Yosemite National Park

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Half Dome & Yosemite Valley

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Chicago → Denver → Las Vegas → Bakersfield → Sequoia National Park → Kings Canyon National Park

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Giant Forest & Kings Canyon drives

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Chicago → Madison → Minneapolis → Fargo → Bismarck → Great Falls → Glacier National Park

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Going-to-the-Sun Road & alpine lakes

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Chicago → Denver → Moab → Grand Canyon → Zion → Bryce Canyon → Yosemite → Sequoia → Las Vegas → Chicago

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15+ parks including Zion, Yosemite, Yellowstone

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Chicago → Minneapolis → Fargo → Winnipeg → Regina → Edmonton → Dawson Creek → Whitehorse → Tok → Fairbanks

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Drive via Yukon to Fairbanks & Denali

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Chicago → Minneapolis → Fargo → Winnipeg → Regina → Edmonton → Dawson Creek → Fort Nelson → Watson Lake → Whitehorse → Tok → Fairbanks → Anchorage

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Complete continent loop

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Chicago → New York City → Boston → Acadia National Park → Quebec City → Toronto → Niagara Falls → Detroit → Chicago → Kansas City → Denver → Salt Lake City → San Francisco → Los Angeles → Las Vegas → Grand Canyon National Park → Dallas → New Orleans → Atlanta → Savannah → Washington D.C. → Chicago

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