Boats for sale in Chicago Illinois

1,218 boats found within 100 miles from Chicago, Illinois

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2026 Chaparral 21 SSi OB

$75,794

Saint Joseph, MI
- Saint Joseph, MI
- Bowrider
- 21'
- 2026 / New
- $75,794
Now on display, see this new 2026 Chaparral 21 SSi powered by a hearty 200 HP Yamaha 4-stroke outboard. Chaparral's innovative use of space means an abundance of cockpit space, sto... View Details

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$75,794
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2023 Viaggio DIAMANTE S 23 TRITOON

$75,999

La Porte, IN
- La Porte, IN
- Pontoon
- 23'
- 2023 / New
- $75,999
New Viaggio Diamante S 23 Tritoon with Full Platinum Package, Power Bimini and BF250 hp Honda, available now at Fay’s Marina in La Porte, Indiana MSRP $126,387, CLEARANCE SALE $7... View Details

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$75,999
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2025 Harris 230 Sunliner

$76,910

Antioch, IL
- Antioch, IL
- Pontoon
- 25'
- 2025 / New
- $76,910
Contact us to find out ALL available savings! With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. The all-new Sunliner delivers the... View Details

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$76,910
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2025 Harris 250 Cruiser

$77,167

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 26'
- 2025 / New
- $77,167
Contact us to find out ALL available savings! Embark on Luxury Adventures with the 2025 Harris 250 Cruiser SL Tri-Toon Experience effortless power and performance with the MERCRUIS... View Details

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$77,167
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1986 Beneteau 13.5 Idylle

$77,800

Chicago, IL
- Chicago, IL
- Sailboat
- 44'
- 1986 / Used
- $77,800
Stock #492637 This Beneteau has recently been added to market (May 27th). Submit your offer today! 1986 Beneteau 13.5 Idylle sailing cruiser ready for water travel! If you are i... View Details

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$77,800
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2016 Regal 2100 SURF

$78,000

Winthrop Harbor, IL
- Winthrop Harbor, IL
- Bowrider
- 0'
- 2016 / Used
- $78,000
New to the market is a fantastic option from Regal boats for the watersports enthusiast. This boat is loaded to the gills with just about every option you can imagine. This is a ve... View Details

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$78,000
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2011 Cobalt 302

$79,990

Fontana, WI
- Fontana, WI
- Bowrider
- 29'
- 2011 / Used
- $79,990
Powered by twin Mercury 350 MAG MPI Bravo III engines, the 302 delivers exhilarating performance, confident handling, and smooth acceleration whether you’re cruising with family, e... View Details

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$79,990
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2021 ATX Surf Boats 20 TYPE-S

$79,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20'
- 2021 / Used
- $79,995
Own the water with this 2021 ATX 20 Type-S. Compact size meets full-size performance for every watersport imaginable-from catching the perfect surf wave to throwing down rampy wake... View Details

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$79,995
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2016 Mastercraft X20

$79,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 20'
- 2016 / Used
- $79,995
66 Hours! The 2016 MasterCraft X20 is the perfect blend of style, performance, and versatility for water enthusiasts. With a sleek design and compact size, this boat is built to de... View Details

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$79,995
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2020 ATX Surf Boats ATX 22

$79,995

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 22'
- 2020 / Used
- $79,995
2020 ATX Surf Boats ATX 22 View Details

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$79,995
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2017 Chaparral 257 SSX

$80,000

Antioch, IL
- Antioch, IL
- Bowrider
- 25'
- 2017 / Used
- $80,000
2017 Chaparral 257 SSX 25' Bow Rider Mercruiser 6.2L, 350hp 380 hours 2017 EZ Loader Tandem Axle Trailer Garmin 741XS Stereo Power Engine Hatch Power Rear Loungers Dual Batteries w... View Details

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$80,000
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2026 Starcraft SLS 3 RL

$80,409

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $80,409
Act fast on this limited-time offer! Experience Luxury on the Water Step aboard the 2026 Starcraft SLS-3 RL and immerse yourself in a world of elegance and exhilaration. With its s... View Details

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$80,409
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2026 Sylvan L3

$81,222

Antioch, IL
- Antioch, IL
- Pontoon
- 24'
- 2026 / New
- $81,222
Act fast on this limited-time offer! The Sylvan L3 CLZ DH, featuring side-by-side dual helm chairs, epitomizes excellence in the realm of performance pontoons. Offering unmatched v... View Details

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$81,222
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2025 Harris 230 Sunliner

$81,368

Walworth, WI
- Walworth, WI
- Pontoon
- 25'
- 2025 / New
- $81,368
Contact us to find out ALL available savings! With flexible seating arrangements and easy style, Sunliner is the pontoon built to fit your family. The all-new Sunliner delivers the... View Details

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$81,368
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2026 Barletta Cabrio 22 Q

$82,844

Antioch, IL
- Antioch, IL
- Pontoon
- 23'
- 2026 / New
- $82,844
Act fast on this limited-time offer! 2026 Barletta CABRIO22Q: Experience Luxury on the Water Unleash your adventurous spirit with the 2026 Barletta CABRIO22Q, a masterpiece of naut... View Details

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$82,844
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2025 Starcraft SLS 3 Q DH

$83,595

Leesburg, IN
- Leesburg, IN
- Pontoon
- 20'
- 2025 / New
- $83,595
OPTIONAL EQUIPMENT INCLUDED WITH THIS UNIT INCLUDE: AUDIO PLUS 225 RADIO UPGRADE W/ REAR FACING SPEAKERS, IN FLOOR STORAGE, RAISED HELM PLATFORM, STAINLESS STEEL WINDSCREEN BRACKET... View Details

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$83,595
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2025 Robalo R202 Explorer

$83,728

Saint Joseph, MI
- Saint Joseph, MI
- Fishing Center Console
- 20'
- 2025 / New
- $83,728
Robalo's R202 Explorer offers the convenience of a center console layout and ease of maintenance, plus expanded seating comfort for a full day of on-water family fun. Well-padded f... View Details

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$83,728
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2026 Barletta Cabrio 22 QC

$84,068

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23'
- 2026 / New
- $84,068
Act fast on this limited-time offer! Experience Luxury on Water Introducing the 2026 Barletta CABRIO22QC, a stunning embodiment of craftsmanship and performance that will elevate y... View Details

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$84,068
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2026 Harris Sunliner 230

$84,936

Antioch, IL
- Antioch, IL
- Pontoon
- 25'
- 2026 / New
- $84,936
Act fast on this limited-time offer! A Life of Luxury Awaits Introducing the 2026 Harris 230SL, where sophistication meets adventure on the water. Experience the thrill of cruising... View Details

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$84,936
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2017 Nautique Super Air Nautique G23

$84,990

Fontana, WI
- Fontana, WI
- Ski & Wake
- 23'
- 2017 / Used
- $84,990
Powered by the PCM ZZ6 450hp direct-injection engine, this boat delivers the torque, precision, and responsiveness serious riders demand—along with the legendary reliability Nautiq... View Details

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$84,990
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2026 Starcraft SLS 3 Q DH

$85,088

Antioch, IL
- Antioch, IL
- Pontoon
- 23'
- 2026 / New
- $85,088
Act fast on this limited-time offer! Experience Unmatched Luxury Introducing the 2026 Starcraft SLS3QDH, your gateway to an exquisite boating lifestyle. This stunning vessel combin... View Details

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$85,088
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