August 31 - September 2 (September 8th)

Open for the season:

Information subject to changes or (eventual) corrections, like the prices.
McHenry "Flashback" series of movies begins on Labor Day weekend.
Many theaters are showing triple features this weekend and open on Sunday (if they weren't already)

Cascade Drive In, W. Chicago, IL (34.2 miles) $10.00
The Incredibles 2 / Jurassic World: Fallen Kingdom / Happytime Murders

49er Drive In, Valparaiso, IN (54.1 Miles) $10.00

The Wizard of Oz / Hotel Transylvania 3: Summer Vacation

McHenry Outdoor Theater, McHenry, IL (57.5 miles) $12.00

Grease / The Rocky Horror Picture Show

RT34 Drive In, Earlville, IL (75.7 miles) $9.00

Christopher Robin / Hotel Transylvania 3:Summer Vacation

Melody Drive In, Knox, IN (95.9 miles) $9.00 

Screen 1: Hotel Transylvania 3: Summer Vacation / Alpha / AXL

Screen 2: Crazy Rich Asians / Mile 22 / Happytime Murders 

Tri-way Drive In, Plymouth, IN (98.7 miles) $9.00

Screen 1: The Meg / Jurassic World: Fallen Kingdom

Screen 2: Christopher Robin / The Incredibles 2

Screen 3: Crazy Rich Asians /  Slender Man
Screen 4: Alpha / Happytime Murders

Lakeshore Drive In, Monticello, IN (117.0 miles) $10.00 
Screen 1: AXL / The Meg
Screen 2: Happytime Murders / Mile 22

Sunset Drive In, Hartford, MI (117.0 miles) $15/car

Christopher Robin / Ant Man and the Wasp

Midway Drive In, Dixon, IL (120 miles) $9.00
Hotel Transylvania 3: Summer Vacation* / Teen Titans Go to the Movies / The Meg
*September 1st and 2nd Only.

Five Mile Drive In, Dowagiac, MI (120.0 miles) $15/car
Crazy Rich Asians / The Meg

Highway 18, Jefferson, WI (126 miles) $9.00
Incredibles 2 / Ant Man and the Wasp / The Equalizer 2 / Angry Red Planet* / Killer Klowns from Outer Space*
(*Dusk until Dawn Features!)

Indexed by Movie: 

Alpha - Melody / Tri-Way
Ant Man and the Wasp - Sunset / Highway 18
AXL - Melody / Lakeshore
Christopher Robin - RT34 / Tri-Way / Sunset
Crazy Rich Asians - Tri-Way / Five Mile
The Equalizer 2 - Highway 18

Happy Time Murders - Cascade / Melody / Tri-Way / Lakeshore 
Hotel Transylvania 3:Summer Vacation - 49er / RT34 / Melody / Midway
Incredibles 2 - Tri-Way / Highway 18
Jurassic World: Fallen Kingdom - Cascade / Tri-Way
The Meg - Melody / Tri-Way / Lakeshore / Midway / Five Mile / Midway
Mile 22 - Melody / Lakeshore 
Slender Man - Tri-Way
Teen Titans Go to the Movies - Midway

Flashback / Classic Movies
Grease - McHenry
The Rocky Horror Picture Show - McHenryWizard of Oz - 49er

Statistics:

11 Open Theaters / 16 screens / 17 movies / 16* unique combinations.
*15 if you count the partial overlap with Lakeshore and Melody.

By distance (Number of screens) (34.2 - 126 miles):
Cascade / 49er / McHenry / RT 34 / Melody (2) / Tri-Way (4) / Lakeshore (2) / Sunset Drive In / Midway / Five Mile Drive In / Highway 18