THINGS TO DO IN HOLIDAY HILLS

Welcome to Holiday Hills! Check out the latest events in town. Explore by location, trending searches, top organizers, and more. Whether you're a local, new to the area, or cruising through, there's no shortage of unique things to do.

Holiday Hills's top activities

Your plans, made easy. Check out Holiday Hills's most popular things to do.

Midwest Travel Network Conference 2026 - McHenry County, IL Sponsorships

Thu, Jun 11, 12:30 PM

The Dole • Crystal Lake, IL

Starts at $321.96

Midwest Travel Network

166 followers

OutdoorCon 2026

Sat, Jun 6, 9:00 AM

Schaumburg Convention Center • Schaumburg, IL

Starts at $23.18

OutdoorCon

Grayslake History Bike Hike

Thu, Jun 4, 6:00 PM

Grayslake Heritage Center • Grayslake, IL

Free

Grayslake Heritage Center Foundation

151 followers

6/9- Algonquin, IL- Gold Rush

Tue, Jun 9, 7:00 PM

Cooper’s Hawk Winery & Restaurant • Algonquin, IL

Starts at $79.00

Cooper's Hawk Winery & Restaurants

19.5k followers

Stewardship + Spring & Summer Bloom Hunt

Tue, May 5, 9:00 AM + 4 more events

Beverly Lake Trail • Hoffman Estates, IL

Free

Friends of the Forest Preserves

882 followers

4th Annual Cowboy Shootout

Sat, May 16, 8:00 AM

Halter Wildlife Inc • Pleasant Prairie, WI

Starts at $28.52

Des Plaines Wetlands Conservancy

12 followers

Chicago's Kite Festival

Sat, May 23, 10:00 AM

Busse Woods • Elk Grove Township, IL

Cloud 9 Creations Events

Discover Your Dream Voyage: An Evening with Princess Cruises

Tue, Jun 9, 6:00 PM

Expedia Cruises • Glenview, IL

Free

Expedia Cruises NorthShore

18 followers

Holiday Hills's top activities

Your plans, made easy. Check out Holiday Hills's most popular things to do.

Midwest Travel Network Conference 2026 - McHenry County, IL *Sponsorships*Midwest Travel Network Conference 2026 - McHenry County, IL *Sponsorships*

OutdoorCon 2026OutdoorCon 2026

Grayslake History Bike HikeGrayslake History Bike Hike

6/9- Algonquin, IL- Gold Rush6/9- Algonquin, IL- Gold Rush

Stewardship + Spring & Summer Bloom HuntStewardship + Spring & Summer Bloom Hunt

4th Annual Cowboy Shootout4th Annual Cowboy Shootout

Chicago's Kite FestivalChicago's Kite Festival

Discover Your Dream Voyage: An Evening with Princess CruisesDiscover Your Dream Voyage: An Evening with Princess Cruises

Midwest Travel Network Conference 2026 - McHenry County, IL Sponsorships

OutdoorCon 2026

Grayslake History Bike Hike

6/9- Algonquin, IL- Gold Rush

Stewardship + Spring & Summer Bloom Hunt

4th Annual Cowboy Shootout

Chicago's Kite Festival

Discover Your Dream Voyage: An Evening with Princess Cruises