2.0 Midlands – Grand Prairie
2.1 Bolingbrook & Lockport
(Northern Will County)
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- Bolingbrook
- White Fence Farm Main Restaurant
- Hidden Lakes Historic Trout Farm
- Plainfield
- The Plainfield Inn
- Village Green Park
- Lockport
- Lockport Lock and Canal
- Des Plaines River & Chicago Sanitary and Ship Canal
- Crest Hill
- Prairie Bluff Preserve
- Lidice Memorial
- Bolingbrook

2.2 Joliet
(County Seat of Will County)
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- City of Steel and Stone (population: 150,000)
- First Dairy Queen opened in 1906
- Old Joliet Prison
- John Wayne Gacy and Baby Face Nelson
- Blues Brothers
- Joliet Area Historical Museum and Route 66 Welcome Center – Joliet Wall Mural
- Old St. Mary Carmelite Church
- Joliet Public Library
- Rialto Square Theatre – “Jewel of Joliet”
- Jacob Henry Mansion – Gilded Age

2.3 Elwood
(Central Will County)
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- Abraham Lincoln National Cemetery
- Joliet Army Training Area
- Joliet Army Ammunition Plant
- Midewin National Tallgrass Prairie

2.4 Wilmington
(Southern Will County)
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- Wilmington (population: 6,000)
- Gemini Giant
- Launching Pad Drive-In
- Town Square & Downtown
- Kankakee River – The Island City
- Braidwood
- “The Little Macaroni Capital”
- Polk-A-Dot Drive In
- Braidwood Zoo
- Godley
- Illinois Mining Museum
- Wilmington (population: 6,000)

2.5 Gardner
(Grundy County)
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- Population: 1,000
- Two Cell Jail
- Historic Streetcar Diner (horse-drawn streetcar/diner)
- Riviera Restaurant (burned down 2010)

2.6 Dwight
(Northern Livingston County)
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- Population: 4,000
- Old Route 66 Family Restaurant
- Ambler’s Texaco Station
- Dwight Train Station
- Prince Albert Prairie Chicken Hunting

2.7 Odell
(Central Livingston County)
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- Odell (population: 1,000)
- Odell Pedestrian Tunnel at St Paul Catholic Church
- Standard Oil Station
- Wishing Well Cafe
- Cayuga: Meramec Caverns Barn Sign
- Odell (population: 1,000)

2.8 Pontiac
(County Seat of Livingston County)
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- Population: 11,000
- Illinois Route 66 Hall of Fame and Museum (Pontiac City Hall and Fire Station)
- Wall Murals
- Livingston County Courthouse
- Livingston County Civil War Memorial