Weekend Getaways Under 2 Hours from Chicago
Five Locations:
🏞️
Lake Geneva, Wisconsin
~1 hr 30 min- Why go: Lakeside chill with spa days, boat tours, and festive winters.
- Highlights: Riviera Beach, the Shore Path, seasonal markets and festivals.
- Best season: Summer for water & beaches; winter for ice castles.
🌲
Starved Rock State Park (Utica, IL)
~1 hr 45 min- Why go: Epic fall colors; in winter, frozen falls and quiet trails.
- Highlights: St. Louis Canyon, guided hikes, easy overlooks for all levels.
- Best season: Fall foliage; winter ice formations.
🍷
New Buffalo & Harbor Country, Michigan
~1 hr 40 min- Why go: Low‑stress beach‑town vibes with great food & drink.
- Highlights: Journeyman Distillery, sunset beaches, fall wine loops.
- Best season: Late spring through early fall.
🧀
Milwaukee, Wisconsin
~1 hr 45 min- Why go: Compact city with craft beer, culture, and lake views.
- Highlights: Lakefront Brewery tour, Harley‑Davidson Museum, Public Market.
- Best season: Summer festivals; winter for museums & markets.
🏰
Galena, Illinois
~2 hrs- Why go: Storybook streets, antiques, and nearby skiing at Chestnut Mountain.
- Highlights: Main Street strolls, U.S. Grant Home, cozy inns.
- Best season: Holiday season & winter; spring for quieter vibes.
Tip: check each destination’s events calendar — small towns often run markets, tours, and festivals that make the trip special.
FAQ
Are these really under two hours?
Drive times are typical without heavy traffic and vary by pickup and conditions. Consider early departures on weekends to beat rushes.
What should we pack for a quick day trip?
Layers, water, snacks, portable chargers, and comfortable shoes. For winter trips, bring traction shoes and a warm hat/gloves.
Any planning tips?
Get a firm headcount, pick one main stop and one backup (weather‑safe), and check parking/entry info on the links above.