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Pontoon Boats For Sale In Chicago, IL
Discover the best Pontoon boats for sale in Chicago, IL.
Explore Pontoon Boats for Sale in Chicago, IL

Bennington 22 MSB 2027
22 MSB | N/A
$11,573 cash down
Bolingbrook, IL

Crest CLASSIC 220 SLC 2025
CLASSIC 220 SLC | 25 Hours
$6,300 cash down
Bolingbrook, IL

Bennington 21 SL 2023
21 SL | N/A
$4,496 cash down
Bolingbrook, IL

Bennington 24 LXSB 2023
24 LXSB | N/A
$9,100 cash down
Bolingbrook, IL

Bennington 18 SXL 2025
18 SXL | N/A
$4,533 cash down
Bolingbrook, IL

Bennington 22 SVSR 2024
22 SVSR | N/A
$4,588 cash down
Bolingbrook, IL

Paddle King LoPro Cruiser 2027
LoPro Cruiser | N/A
$2,670 cash down
Wauconda, IL

Odyssey 222C 2006
222C | N/A
$1,500 cash down
Wauconda, IL
Search The Best Boats Deals In Illinois

Paddle King Lo Pro Cruiser XL 2026
Lo Pro Cruiser XL | N/A
$3,100 cash down
Wauconda, IL

Paddle King Lo Pro Fisher 2026
Lo Pro Fisher | N/A
$2,020 cash down
Wauconda, IL

Angler Quest 816 Panfish Cruise 2025
816 Panfish Cruise | N/A
$3,060 cash down
Wauconda, IL

Crest Crest II 240 LS 2019
Crest II 240 LS | 268 Hours
$3,500 cash down
Lake in the Hills, IL

Xcursion X23RFE 2013
X23RFE | 466 Hours
$1,800 cash down
Lake in the Hills, IL

Sylvan Mirage 820 LZ w Change Room 2022
Mirage 820 LZ w/ Change Room | 101 Hours
$3,000 cash down
Lake in the Hills, IL

South Bay 222RS LE 275 2024
222RS LE 275 | 10 Hours
$4,500 cash down
round lake, IL

Bennington 22 SSB 2024
22 SSB | 179 Hours
$4,800 cash down
Round Lake, IL

Bentley Pontoons 220223 Elite Admiral 2017
220/223 Elite Admiral | N/A
$2,500 cash down
Round Lake, IL
Chicago boats from $199/mo
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Catamaran
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Recent Boat Buying Tips & Reviews
Boat Wrap Cost in 2026: What You’ll Really Pay for Vinyl, Shrink Wrap, and Yacht Wraps
Key Takeaways A professional boat wrap cost for most trailerable boats falls between $1,200 and $7,500. Yachts can exceed $15,000. Winter shrink wrap is a separate, recurring expense, typically $17…
5 minutes | September, 29, 2026Boat Rental Cost: What You’ll Really Pay on the Water
Key Takeaways A typical boat rental cost runs 350–900 per day for self-drive pontoons, bowriders, and small center consoles. Captains add roughly 300–500 per day, plus a 15–20% tip. Fuel,…
6 minutes | October, 20, 2026Boat Trailer Cost: What You’ll Really Pay in 2026
Key Takeaways Most new trailers cost 1,500–9,000. Heavy triple-axle models can exceed $20,000. Aluminum trailers usually run 15–30% more than galvanized steel but handle saltwater better. Registration, brakes, spares, and…
5 minutes | October, 26, 2026How Much Is a Bass Boat? Real Prices, From Starter Rigs to Tournament Boats
Key Takeaways How much is a bass boat in 2026? Expect about $3,500 for older used aluminum and $100,000+ for loaded tournament rigs. New aluminum starts near $17,000. New entry-level…
6 minutes | October, 15, 2026Cost to Repower a Boat in 2026: What Owners Really Pay
Key Takeaways The average cost to repower a boat ranges from about $8,000 for a small outboard to $150,000+ for twin diesel inboards. Labor typically adds 10–25% to the engine…
6 minutes | October, 26, 2026Outboard Motor Cost in 2026: What You’ll Really Pay, From 20 HP to Twin 250s
Key Takeaways The average new outboard sold in the U.S. in 2025 cost about $13,081, according to NMMA. Small portables (2.5–20 HP) typically run 1,000–4,800 new. A new Yamaha 150…
6 minutes | October, 19, 2026Popular Boat Makes in Chicago
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