GarageCherries
Oswego, IL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Oswego, Illinois.
13 upcoming events in Oswego
Browse cars for sale in Illinois →Get this weekend's car shows near you, every Thursday
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Upcoming Events in Oswego
Oct
21
Oswego Chamber of Commerce Byline Bank Cruise Nights
Oct 21, 2026 · Oswego, IL
Regular cars and coffee / cruise-in gathering in Oswego, IL, drawing classic cars, hot rods, and collector vehicles.
Nov
21
Downtown Oswego Cruise Nights
Nov 21, 2026 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
Dec
16
Oswego Chamber of Commerce Byline Bank Cruise Nights
Dec 16, 2026 · Oswego, IL
Regular cars and coffee / cruise-in gathering in Oswego, IL, drawing classic cars, hot rods, and collector vehicles.
Dec
19
Downtown Oswego Cruise Nights
Dec 19, 2026 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
Jan
9
Downtown Oswego Cruise Nights
Jan 9, 2027 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
Jan
16
Downtown Oswego Cruise Nights
Jan 16, 2027 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
Feb
17
Oswego Chamber of Commerce Byline Bank Cruise Nights
Feb 17, 2027 · Oswego, IL
Regular cars and coffee / cruise-in gathering in Oswego, IL, drawing classic cars, hot rods, and collector vehicles.
Feb
20
Downtown Oswego Cruise Nights
Feb 20, 2027 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
Mar
13
Downtown Oswego Cruise Nights
Mar 13, 2027 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
Apr
17
Downtown Oswego Cruise Nights
Apr 17, 2027 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
May
19
Oswego Chamber of Commerce Byline Bank Cruise Nights
May 19, 2027 · Oswego, IL
Regular cars and coffee / cruise-in gathering in Oswego, IL, drawing classic cars, hot rods, and collector vehicles.
Jun
12
Downtown Oswego Cruise Nights
Jun 12, 2027 · Oswego, IL
Car show in Oswego, IL, featuring classic, custom, and collector vehicles on display.
Jun
16
Oswego Chamber of Commerce Byline Bank Cruise Nights
Jun 16, 2027 · Oswego, IL
Regular cars and coffee / cruise-in gathering in Oswego, IL, drawing classic cars, hot rods, and collector vehicles.
Car Shows in Nearby Cities
Cars for sale in Illinois
1980 Ford Shay Model A Replica
Excellent1962 Chevrolet Impala
1983 Ford Econoline Wagon E150 Custom Van
Good1976 Cadillac Eldorado Convertible
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.