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McHenry Cruise Night on Green Street (McHenry)
Date: Mondays, Through October 5, 2026 | 5:00 PM – 8:00 PM
Venue: 1208 N Green St, McHenry, IL 60050
Details: Admission and display parking are free for this regular Monday night cruise-in on historic Green Street. The event brings together a wide variety of vintage automobiles, street machines, hot rods, and collector vehicles. Spectators can stroll the block, admire classic engine builds, and grab dinner or drinks from neighboring downtown McHenry pubs and eateries. It delivers a relaxed, small-town street cruising vibe with plenty of local camaraderie.
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Car & Bike Show at Broken Oar (Port Barrington)
Date: Tuesdays, Through October 3, 2026 | 5:00 PM
Venue: Broken Oar, 614 Rawson Bridge Rd, Port Barrington, IL 60010
Details: Head to Broken Oar every Tuesday night for a free summer Car & Bike Show featuring custom cars, motorcycles, weekly trophies, and a laid-back lakeside atmosphere. Both spectators and vehicle entries are welcome free of charge, and registered exhibitors receive a free coupon to use at the restaurant. Enjoy the cars, scenic views, food, drinks, and weekly awards at this popular Tuesday night gathering.
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Rand Red Hots Classic Car Cruise Night (Des Plaines)
Date: Tuesdays, Through September 15, 2026 | 5:00 PM – 9:00 PM
Venue: Rand Red Hots, Des Plaines
Details: A weekly cruise night featuring classic cars, muscle cars, hot rods, and custom vehicles. Visitors can enjoy great food, meet local car enthusiasts, and browse a rotating collection of vintage automobiles.
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Image source: Rand Red Hots
Wauconda Cruise Night (Wauconda)
Date: Tuesday, September 15, 2026 | 5:00 PM - 8:00 PM
Venue: Downtown Wauconda, Main Street, Wauconda, IL 60084
Details: Cruise into downtown Wauconda for a family-friendly evening featuring hundreds of classic cars, muscle cars, hot rods, motorcycles, and more. Enjoy the impressive lineup of vehicles, grab some food, and take in the lively community atmosphere along Main Street. The event is free for both cruisers and spectators.
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Cruise Night Car Show at 120 Live (Bartlett)
Date: Wednesdays, Through September 30, 2026 | 5:00 PM – 8:00 PM
Venue: Bartlett Metra Lot (adjacent to 120 Live), 266 E Railroad Ave, Bartlett, IL 60103
Details: This weekly Wednesday evening cruise night offers free admission and open display parking for all makes, models, and eras. The showcase features vintage muscle, antique trucks, hot rods, and modern exotics lining the commuter lot. Guests can take advantage of indoor/outdoor seating, half-priced pizza specials, cold craft drinks, and music by DJ Arty. It delivers an upbeat, community-centric block party vibe right in downtown Bartlett.
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Rescheduled Date - Niles Cruise Nights Car Show (Niles)
Date: Wednesday, September 16, 2026 | 5:00 PM - 8:00 PM
Venue: Golf Mill Park, 9101 Greenwood Ave., Niles, IL 60714
Details: The rescheduled Niles Cruise Nights Car Show brings a lineup of cars and automotive enthusiasts to Golf Mill Park for an evening of cruising, conversation, and community. Stop by to check out the vehicles, meet fellow car lovers, and enjoy this free community event.
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Car Fun on 21: Live Music & Classic Car Show (Libertyville)
Date: Wednesday, September 16, 2026 | 6:00 PM - 9:00 PM
Venue: Downtown Libertyville, Church Street and Cook Street, Libertyville, IL 60048
Details: Spend the evening in downtown Libertyville checking out a lineup of classic cars while enjoying live music and the lively atmosphere along Church and Cook Streets. It’s a great midweek outing for car enthusiasts, families, and anyone looking to enjoy an evening downtown.
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Al's Hot Dogs Cruise Nights (Long Grove)
Date: Wednesdays,Through September , 2026 | 3:00 PM – 9:00 PM
Venue: Al's Hot Dogs, Long Grove
Details: One of the area's longest-running cruise nights with classic cars, customs, trucks, and motorcycles. Food, music, and a relaxed atmosphere make it a favorite midweek destination for enthusiasts.
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Image source: Felix Greco
Roselle American Legion Cruise Night (Roselle)
Date: Fridays, Through September 18, 2026 | 6:00 PM – 9:00 PM
Venue: American Legion Hall
Details: Weekly cruise night featuring classic cars, muscle cars, and customs with food, music, and refreshments while supporting local veterans through the American Legion.
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Image source: Raymond Bombeck
Community Classic Car Show at The Grand (Palatine)
Date: Friday, September 18, 2026 | 4:00 PM - 6:30 PM
Venue: The Grand at Twin Lakes, 920 E. Northwest Highway, Palatine, IL 60074
Details: Rev up for a free community classic car show at The Grand at Twin Lakes featuring classic cars, great music, vendors, and raffle baskets. All classic cars are welcome, making this a fun evening for car enthusiasts and families. Parking is available in the Cotillion Banquets lot, with the show taking place in The Grand’s back lot.
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West Dundee Heritage Fest Car Show & Live Music
Date: Saturday, September 19, 2026 | 10:30 AM - 4:00 PM
Venue: South Second Street, Downtown West Dundee, West Dundee, IL 60118
Details: Head to Heritage Fest for a full day of classic and custom vehicles, with antiques, originals, rat rods, trucks, motorcycles, and more lining South Second Street. Vote for your favorite ride and enjoy plenty of food, vendors, and live music throughout the festival. Saturday’s entertainment includes Crossover, Bishop Super Band, Peach Fuzz, The Eric Case Band, Sixes & Sevens, and 7th Heaven. General admission is free.
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Stade’s 21st Annual Classic Car, Truck & Tractor Show (McHenry)
Date: Saturday, September 19 & Sunday, September 20, 2026 | 10:00 AM - 6:00 PM
Venue: Stade’s Farm & Market, 3709 Miller Road, McHenry, IL 60051
Details: Head to Stade’s Farm & Market for its 21st annual celebration of classic vehicles, featuring a display of classic cars, trucks, and tractors. It’s a great weekend stop for automotive enthusiasts and families to check out the vehicles while enjoying the farm market atmosphere.
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Bluesmobile Cruise Nights: Make-Up Night (Mount Prospect)
Date: Saturdays, Through September 26, 2026 | 3:00 PM – 8:00 PM
Venue: Downtown Mount Prospect (Metra East Commuter Lot)
Details: One of Chicagoland's largest cruise nights. This themed event highlights emergency vehicles alongside hundreds of classic cars, hot rods, muscle cars, and specialty vehicles. Food vendors, music, and family activities round out the evening.
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Image source: Mount Prospect Lions Club
RTBE: Crave & Cars Car Show & Vendor Market (Hanover Park)
Date: Saturday, September 19, 2026 | 6:00 PM - 9:00 PM
Venue: Crave Restaurant, 1053 Lake St, Hanover Park, IL 60133
Details: Head to The Crave Restaurant for a fun evening of cars, food, prizes, and local vendors. The car show welcomes all builds, with prizes throughout the night and a vendor market running from 6–9 PM. Grab food from The Crave, which will stay open until midnight, and enjoy a night of cars and good vibes with the community.
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Classic Cars Cruise Night at Steak 'N Shake (Elgin)
Date: Saturdays, Through October 24, 2026 | 4:00 PM – 11:00 PM
Venue: Steak 'n Shake, Elgin
Details: A casual Saturday evening gathering featuring classic cars, customs, muscle cars, and modern performance vehicles. Grab dinner while enjoying an ever-changing lineup of automotive favorites.
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Image source: Old Cars, Strong Hearts
VW-FEST 2026 Car Show and Swap Meet (Crystal Lake)
Date: Sunday, September 20, 2026 | 9:00 AM - 2:30 PM
Venue: Fox Valley Volkswagen of Crystal Lake, 5213 W. Northwest Hwy., Crystal Lake, IL 60014
Details: Join the Northeast Illinois Volkswagen Association for a celebration of all things Volkswagen, featuring an all-VW car show and swap meet. Enjoy a lineup of Volkswagen vehicles, DJ entertainment, food and ice cream trucks, dash plaques, event T-shirts, and participant judging. All VW models are welcome, and spectators can attend for free. Car registration is $20 cash, with swap spaces also available.
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Des Plaines Fall Fest Custom Car Show (Des Plaines)
Date: Sunday, September 20, 2026 | 9:30 AM - 2:00 PM
Venue: Lakeview Center, 1177 Howard Ave, Des Plaines, IL 60018
Details: Part of Des Plaines Fall Fest, this custom car show brings a variety of eye-catching vehicles to the Lakeview Center throughout the weekend. Car enthusiasts can check out the lineup while enjoying Fall Fest’s food, live music, carnival, and family activities nearby.
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