“Look at life through the windshield, not the rearview mirror.” – Byrd Baggett
Sometimes, all you need is to pack your bags and get behind the wheel. Chicago boasts proximity to many dreamy, touristy, magical towns to make your worries vroooom away.
Mystical Oval Beach at Saugatuck, a charming Michigan town
Here it goes, in order of driving distance from Chicago:
1. Lake Geneva (IL)
Distance: 80 miles
ETA: 1.5 hours
Things To Do: Here
Coveted Lake Shore Path, courtesy VisitLakeGeneva.com
Why Lake Geneva?
A splendid lake with a super-equipped beach, the eminent Million Dollar Walk at Lake Shore Path (~ 25 miles) with multi-million dollar mansions for company, a plethora of adventure activities offered by Lake Geneva Adventures – zip line, hiking, biking, obstacle courses, and finally, numerous lake activities including boat rentals – no wonder Lake Geneva attracts people in droves all year.
People asceding the zipline tower, courtesy Lake Geneva Adventures
2. Galena (IL)
Distance: 150 miles.
ETA: 2.5 hours
Detailed Blog: Here
Things To Do: Here
Soaring Eagle Ride in picturesque Chestnut Mountain Resort
Why Galena?
An all season destination – you can go for its skiing, sledding, snowshoeing opportunities in winter and in warmer months, you can enjoy the balloon race, scenic hikes, cultural amusements & the many family frolics at Chestnut Mountain Resort – Alpine Slide, Soaring Eagle and more. Don’t miss the walk at historical Main Street with many notable local restaurants. The easy 1-mile hike at the Horseshoe Mound Preserve, with its panoramic views and elevation changes is not to be missed.
Horseshoe Mound Viewing Area, courtesy Ed@AllTrails
Balloon rides are a major attraction, courtesy: Buyaballoonride.com
3. Saugatuck (MI)
Distance: 150 miles
ETA: 2.5 hours
Detailed Blog: Here
Things To Do: Here
Saugatuck’s acclaimed Oval Beach
Why Saugatuck?
If you ever yearn for a dreamy coastal town by the Lake Michigan and Kalamazoo River – dripping with local festivities like the renowned Dune Rides, sumptuous food, scenic Saugatuck Dunes State Park, arts and multiple beaches offering water activities for family – look no further than Saugatuck!
Don’t miss the coveted Dune Rides, Courtesy Saugatuck.com
Uncommon Coffee House – one of Saugatuck’s downtown local gems
4. Madison (WI)
Distance: 150 miles
ETA: 2.5 hours
Things To Do: Visit Madison
Why Madison?
The well-known Midwest city is a catnip for tourists for its outdoor activities, museums, farmers markets, Memorial Union Terrace, botanical garden, Cave of the Mounds and the Wisconsin State Capitol.
Vibrant biking opportunities at Madison, courtesy Visit Madison
Tip: Madison is one of top 5 bicycle friendly cities in US per 2023 survey.
5. Door County (WI)
Distance: 270 miles
ETA: 4-5 hours
Detailed Blog: Here
Things To Do: Door County, Sister Bay
Door County is great all year, but especially mystic during Fall
Why Door County?
300 miles of shoreline, 10 waterfront towns, 5 state parks including one designated Dark Sky park, 11 lighthouses attracting over 2 million visitors per year. The Cape Cod of the Midwest is a must-visit destination for any MidWesterner in any season – Spring, Summer and especially Fall!
The 2-mile Eagle Trail at Peninsula State Park is moderately difficult due to rocky terrain but easily the best hike, especially during Summer and Fall.
Eagle Tower, Courtesy Wisconsin DNR
Sister Bay is prominently known for numerous summer and fall festivities, always fun to spend time there regardless of season.
Use the unique rentals to explore Door County, courtesy Door County Slingshots
Other Notable Destinations
New Buffalo, MI
Devil’s Lake, WI
That’s it! Hope this helps you plan your next Chicago Weekend Road Trip.
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