Places in this collection
Milwaukee
attractionMilwaukee, United States
Underrated city with great brunch spots (try a loaded Bloody Mary with a sidecar), Summerfest, Discovery World Museum, and a children's museum.
View on Google MapsMackinac Island
attractionMichigan 49757
An island destination located 7-9 hours from Chicago.
View on Google MapsPortland
attractionMaine
Start your trip here for 2-3 nights. Walk the Old Port, see lighthouse views, enjoy sunsets by the water, and experience an incredible food scene.
View on Google MapsHistoric Galena
attraction500 Bouthillier St, Galena, IL 61036, United States
A historic town known for its log cabin, fine food, and cocktails, 3 hours from Chicago.
View on Google MapsAcadia National Park
attractionMaine
Part of the Bar Harbor stop. Must-see moments include sunrise at Cadillac Mountain, Jordan Pond walk, Park Loop Road, and Ocean Path.
View on Google MapsMariner's Restaurant
restaurant35 Main St, Camden, ME 04843
A restaurant in Camden, mentioned as an optional stop.
View on Google MapsCadillac Mountain
attractionBar Harbor, ME 04609
Experience sunrise at Cadillac Mountain.
View on Google MapsFerne Clyffe State Park
attraction90 Goreville Rd, Goreville, IL 62939
Happy Hollow Trail: 7.6 km, 111 m gain, estimated 1 hour 44 minutes.
View on Google MapsBar Harbor
otherBar Harbor, ME
The heart of the trip for 3-4 nights. Experience mountains and ocean, scenic drives, small town nights, and nature everywhere.
View on Google MapsJordan Pond
attractionMt Desert, ME
Enjoy a walk around Jordan Pond.
View on Google MapsStarved Rock State Park
attractionOglesby, IL 61348, United States
A state park located 2-2.5 hours from Chicago.
View on Google MapsCamp Aramoni
accommodation818 N 2219th Rd, Tonica, IL 61370
Luxury glamping with limited cabins, located about 90 minutes from Chicago, near Starved Rock State Park and Mattheson State Park.
View on Google MapsCache River State Natural Area
activity930 Sunflower Ln, Belknap, IL 62908, United States
Cache River and Heron Pond Boardwalk: 11.3 km, 95 m gain, estimated 2 hours 19 minutes.
View on Google MapsSaugatuck Chain Ferry
activity528 Water St, Saugatuck, MI 49453, United States
A ferry service in Saugatuck, MI, part of the 'Art Coast of Michigan', 2.5-3 hours from Chicago.
View on Google MapsPeaks Island
attractionPortland, ME
Take a day trip to Peaks Island from Portland.
View on Google MapsMatthiessen State Park
attraction2500 IL-178, Oglesby, IL 61348
Dells Canyon and Bluff Trail: 3.5 km, 70 m gain, estimated 53 minutes. Spotty service reported, download before you go.
View on Google MapsCamden
attractionMaine
An optional stop if you have time, offering harbor views, a quiet downtown, and a mountain overlook.
View on Google MapsThe House on the Rock
attraction5754 WI-23, Spring Green, WI 53588
A unique attraction located 3.5 hours from Chicago.
View on Google MapsGarden of the Gods
attractionHerod, IL 62947
Observation Trail: 0.8 km, 12 m gain, estimated 11 minutes.
View on Google MapsDoor County
attractionDoor County, WI, USA
A favorite destination with many outdoor activities like hiking, biking, and kayaking. Features great restaurants, a drive-in movie theatre, and Al Johnson's Swedish restaurant with goats on the roof.
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