Auto, boat & air events in South Milwaukee, WI
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Season Opener with Midwest Powerwheels at Great Lakes Dragaway
Sat, Apr 18, 10:00 AM
Union Grove · 18411 1st St
Season Opener with Midwest Powerwheels at Great Lakes Dragaway
Sat, Apr 18, 10:00 AM
Union Grove · 18411 1st St
2nd annual Jeeps 4 Vets Powerwheels drag race "22 a day in May"
Sun, May 17, 1:00 PM
Grayslake · Downtown Grayslake
2nd annual Jeeps 4 Vets Powerwheels drag race "22 a day in May"
Sun, May 17, 1:00 PM
Grayslake · Downtown Grayslake
2026 TUNER GALLERIA Chicago Car Show
Sat, Mar 7, 12:00 PM
Rosemont · Donald E Stevens Convention Center
2026 TUNER GALLERIA Chicago Car Show
Sat, Mar 7, 12:00 PM
Rosemont · Donald E Stevens Convention Center
Original Lowrider Chicago Classic Supershow
Sun, Aug 9, 11:00 AM
Rosemont · Donald E. Stephens Convention Center
Original Lowrider Chicago Classic Supershow
Sun, Aug 9, 11:00 AM
Rosemont · Donald E. Stephens Convention Center
MIDWEST WOMEN RIDERS - GYGO2026 - WORLD RECORD FEMALE RIDE
Thu, Jun 11, 12:00 PM
Rockford · Hard Rock Casino Rockford
MIDWEST WOMEN RIDERS - GYGO2026 - WORLD RECORD FEMALE RIDE
Thu, Jun 11, 12:00 PM
Rockford · Hard Rock Casino Rockford
2026 Nautical Education: Phil Pollard PFD Safety Gear Seminar
Sat, Mar 7, 11:00 AM
Chicago · 400 E Monroe St
2026 Nautical Education: Phil Pollard PFD Safety Gear Seminar
Sat, Mar 7, 11:00 AM
Chicago · 400 E Monroe St
Sunday Night Skyline Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Sun, Sep 6, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Sunday Night Skyline Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Sun, Sep 6, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Memorial Day Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Mon, May 25, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Memorial Day Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Mon, May 25, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Air & Water Show Sunday Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Sun, Aug 16, 12:00 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Air & Water Show Sunday Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Sun, Aug 16, 12:00 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Friday Night Skyline Cruises on Lake Michigan | 21+ | Live DJ | Full Bar
Fri, May 1, 8:30 PM + 20 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Friday Night Skyline Cruises on Lake Michigan | 21+ | Live DJ | Full Bar
Fri, May 1, 8:30 PM + 20 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Labor Day Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Mon, Sep 7, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Labor Day Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Mon, Sep 7, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Saturday Happy Hour Cruises on Lake Michigan | 21+ | Live DJ | Full Bar
Sat, May 9, 4:30 PM + 20 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Saturday Happy Hour Cruises on Lake Michigan | 21+ | Live DJ | Full Bar
Sat, May 9, 4:30 PM + 20 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Saturday Night Fireworks Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Sat, May 23, 8:30 PM + 14 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Saturday Night Fireworks Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Sat, May 23, 8:30 PM + 14 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Saturday Afternoon Cruises on Lake Michigan | 21+ | Live DJ | Full Bar
Sat, May 23, 12:30 PM + 14 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Saturday Afternoon Cruises on Lake Michigan | 21+ | Live DJ | Full Bar
Sat, May 23, 12:30 PM + 14 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Wednesday Fireworks Cruises on Lake Michigan | 21+ | Full Bar
Wed, May 27, 7:30 PM + 13 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Wednesday Fireworks Cruises on Lake Michigan | 21+ | Full Bar
Wed, May 27, 7:30 PM + 13 more
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
July 3rd Happy Hour Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Fri, Jul 3, 4:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
July 3rd Happy Hour Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Fri, Jul 3, 4:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
July 2nd Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Thu, Jul 2, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
July 2nd Cruise on Lake Michigan | 21+ | Live DJ | Full Bar
Thu, Jul 2, 8:30 PM
Chicago · Sightseer Boat located at Monroe Harbor (See map and directions at bottom of page for exact location)
Frequently asked questions about South Milwaukee