Chicago

Feel the authentic vibe and scenic grace of the picturesque city of Chicago, located in Illinois.

Tucked away in the scenic landscapes of Illinois, Chicago stands out as a remarkable destination filled with character and natural grace.

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Knot My Boat Charters
United States
Captain Justin Pasciak in Chicago Illinois United States
Captain Justin Pasciak in Chicago Illinois United States
From
300 USD
1445 views
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BIP Boating
United States
Victory Lap Yacht Private Charter in Chicago Illinois United States
Victory Lap Yacht Private Charter in Chicago Illinois United States
From
900 USD
955 views
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Chicago Blue Water Charters
United States
Sunset Tour in Chicago Illinois United States
Sunset Tour in Chicago Illinois United States
From
225 USD
1105 views
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Kayak Chicago in
United States
2 Hour Kayak Rental North Avenue Beach in Chicago Illinois United States
2 Hour Kayak Rental North Avenue Beach in Chicago Illinois United States
From
70 USD
960 views
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Chicago Blue Water Charters
United States
Speed Boat Rides in Chicago Illinois United States
Speed Boat Rides in Chicago Illinois United States
From
225 USD
1138 views
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Blackhawk Boat Tours LLC
United States
LAKE ADVENTURE TOUR in Chicago Illinois United States
LAKE ADVENTURE TOUR in Chicago Illinois United States
From
60 USD
1299 views
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Knot My Boat Charters
United States
46ft Sea Ray Express in Chicago Illinois United States
46ft Sea Ray Express in Chicago Illinois United States
From
950 USD
1302 views
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Blackhawk Boat Tours LLC
United States
Adventure Lake and River Tour in Chicago Illinois United States
Adventure Lake and River Tour in Chicago Illinois United States
From
85 USD
1275 views
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Luxury Jet Cars LLC
United States
Hurricane Rose in Chicago Illinois United States
Hurricane Rose in Chicago Illinois United States
From
599 USD
1478 views
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Chicago Boat Rentals
United States
18 FT Private Pontoon Cruise in Chicago Illinois United States
18 FT Private Pontoon Cruise in Chicago Illinois United States
From
150 USD
876 views
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Knot My Boat Charters
United States
48ft Sea Ray Flybridge in Chicago Illinois United States
48ft Sea Ray Flybridge in Chicago Illinois United States
From
1000 USD
1044 views
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Endless Summer Chi
United States
Fireworks Cruise Endless Summer in Chicago Illinois United States
Fireworks Cruise Endless Summer in Chicago Illinois United States
From
1000 USD
1525 views
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Ace Yachting
United States
Chicago River Cruise - Navy Pier and River Tour in Chicago Illinois United States
Chicago River Cruise - Navy Pier and River Tour in Chicago Illinois United States
From
807 USD
1074 views
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Chicago Boat Rentals
United States
Evening Boat Rentals Fireworks in Chicago Illinois United States
Evening Boat Rentals Fireworks in Chicago Illinois United States
From
350 USD
1350 views
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Tall Ship Windy
United States
Fireworks Cruise in Chicago Illinois United States
Fireworks Cruise in Chicago Illinois United States
From
65 USD
1401 views
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Tall Ship Windy
United States
Contemporary Chicago Blues LIVE with Michael Charles in Chicago Illinois United States
Contemporary Chicago Blues LIVE with Michael Charles in Chicago Illinois United States
From
49 USD
1160 views
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Knot My Boat Charters
United States
Taylor Breutzmann in Chicago Illinois United States
Taylor Breutzmann in Chicago Illinois United States
From
300 USD
878 views
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Knot My Boat Charters
United States
Capt Michael Gabiga in Chicago Illinois United States
Capt Michael Gabiga in Chicago Illinois United States
From
300 USD
904 views
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Believe Chicago
United States
Sea Ray 450 Believe Chicago in Chicago Illinois United States
Sea Ray 450 Believe Chicago in Chicago Illinois United States
From
1135 USD
1038 views
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Chicago Blue Water Charters
United States
Fireworks Tour in Chicago Illinois United States
Fireworks Tour in Chicago Illinois United States
From
250 USD
1095 views
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Knot My Boat Charters
United States
Captain Tony Cartagena in Chicago Illinois United States
Captain Tony Cartagena in Chicago Illinois United States
From
300 USD
1507 views
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Endless Summer Chi
United States
Day Cruise Endless Summer in Chicago Illinois United States
Day Cruise Endless Summer in Chicago Illinois United States
From
1050 USD
1409 views
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Knot My Boat Charters
United States
Captain Brian Haas in Chicago Illinois United States
Captain Brian Haas in Chicago Illinois United States
From
400 USD
1373 views
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Kayak Chicago in
United States
2 Hour Kayak SUP Rentals Montrose Beach in Chicago Illinois United States
2 Hour Kayak SUP Rentals Montrose Beach in Chicago Illinois United States
From
70 USD
993 views
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Seabird Sailing
United States
Private Couples Weeknight Sailing Charter in Chicago Illinois United States
Private Couples Weeknight Sailing Charter in Chicago Illinois United States
From
300 USD
1049 views
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Knot My Boat Charters
United States
Captain Rich Wallace in Chicago Illinois United States
Captain Rich Wallace in Chicago Illinois United States
From
300 USD
1433 views
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Ace Yachting
United States
Bachelor Bachelorette Party Cruise - 13 Guests in Chicago Illinois United States
Bachelor Bachelorette Party Cruise - 13 Guests in Chicago Illinois United States
From
538 USD
1343 views
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Kayak Chicago
United States
Sunset on the Chicago River in Chicago Illinois United States
Sunset on the Chicago River in Chicago Illinois United States
From
69 USD
966 views
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Seabird Sailing
United States
Private Weeknight Sailing Charter in Chicago Illinois United States
Private Weeknight Sailing Charter in Chicago Illinois United States
From
450 USD
1172 views
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Luxury Jet Cars LLC
United States
Spongebob in Chicago Illinois United States
Spongebob in Chicago Illinois United States
From
999 USD
1401 views
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Kayak Chicago
United States
Fireworks Tour in Chicago Illinois United States
Fireworks Tour in Chicago Illinois United States
From
69 USD
871 views
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Chicago Blue Water Charters
United States
Yacht Tours Fishing in Chicago Illinois United States
Yacht Tours Fishing in Chicago Illinois United States
From
900 USD
1306 views
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Tall Ship Windy
United States
Fireworks Cruise in Chicago Illinois United States
Fireworks Cruise in Chicago Illinois United States
From
69 USD
937 views
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Luxury Jet Cars LLC
United States
The Riddler in Chicago Illinois United States
The Riddler in Chicago Illinois United States
From
1099 USD
1343 views
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Knot My Boat Charters
United States
56ft Sea Ray Sundancer in Chicago Illinois United States
56ft Sea Ray Sundancer in Chicago Illinois United States
From
1200 USD
1031 views
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Chicago Fireboat Tours
United States
Historical and Architectural Lake River Tour in Chicago Illinois United States
Historical and Architectural Lake River Tour in Chicago Illinois United States
From
33 USD
1389 views
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Chicago Sailboat and Yacht Charters
United States
51 Sea Ray Sundancer Powerboat in Chicago Illinois United States
51 Sea Ray Sundancer Powerboat in Chicago Illinois United States
From
1580 USD
1525 views
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Kayak Chicago
United States
Intermediate Kayaking in Chicago Illinois United States
Intermediate Kayaking in Chicago Illinois United States
From
95 USD
1417 views
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BIP Boating
United States
Request Chez Ren e Luxury Yacht Charter in Chicago Illinois United States
Request Chez Ren e Luxury Yacht Charter in Chicago Illinois United States
From
1200 USD
1108 views
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Tall Ship Windy
United States
Chicago Skyline Sail in Chicago Illinois United States
Chicago Skyline Sail in Chicago Illinois United States
From
10 USD
1053 views
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Kayak Chicago
United States
Learn to Kayak in Chicago Illinois United States
Learn to Kayak in Chicago Illinois United States
From
69 USD
1422 views
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Kayak Chicago in
United States
1 Hour Kayak SUP Rentals Montrose Beach in Chicago Illinois United States
1 Hour Kayak SUP Rentals Montrose Beach in Chicago Illinois United States
From
35 USD
1101 views
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Luxury Jet Cars LLC
United States
Bonnie Clyde in Chicago Illinois United States
Bonnie Clyde in Chicago Illinois United States
From
599 USD
876 views
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Poseidon Chicago Charters
United States
Fireworks Cruise in Chicago Illinois United States
Fireworks Cruise in Chicago Illinois United States
From
900 USD
1311 views
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Kayak Chicago in
United States
2 Hour Kayak Rental Chicago River in Chicago Illinois United States
2 Hour Kayak Rental Chicago River in Chicago Illinois United States
From
60 USD
1239 views
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Ace Yachting
United States
Yacht Charter Cruise - 13 Guests in Chicago Illinois United States
Yacht Charter Cruise - 13 Guests in Chicago Illinois United States
From
538 USD
879 views
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BIP Boating
United States
Request 42 Custom Built Power Catamaran in Chicago Illinois United States
Request 42 Custom Built Power Catamaran in Chicago Illinois United States
From
2000 USD
932 views
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Angelas Charters
United States
Private Yacht Charter for Up to 25 Guests in Chicago Illinois United States
Private Yacht Charter for Up to 25 Guests in Chicago Illinois United States
From
2400 USD
988 views
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Knot My Boat Charters
United States
37ft Sea Ray Sundancer in Chicago Illinois United States
37ft Sea Ray Sundancer in Chicago Illinois United States
From
825 USD
1349 views
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Knot My Boat Charters
United States
Captain John Brown in Chicago Illinois United States
Captain John Brown in Chicago Illinois United States
From
300 USD
990 views
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Chicago Fireboat Tours
United States
2026 Air Show Cruises in Chicago Illinois United States
2026 Air Show Cruises in Chicago Illinois United States
From
204 USD
996 views
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Knot My Boat Charters
United States
Captain Dan Leslie in Chicago Illinois United States
Captain Dan Leslie in Chicago Illinois United States
From
375 USD
1312 views
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WeVenture Chicago
United States
Chicago River by Private Boat in Chicago Illinois United States
Chicago River by Private Boat in Chicago Illinois United States
From
625 USD
1136 views
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Kayak Chicago
United States
Intro to Stand-Up Paddleboard in Chicago Illinois United States
Intro to Stand-Up Paddleboard in Chicago Illinois United States
From
75 USD
951 views
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Knot My Boat Charters
United States
Captain Ian Barbosa in Chicago Illinois United States
Captain Ian Barbosa in Chicago Illinois United States
From
300 USD
952 views
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Knot My Boat Charters
United States
50ft Sea Ray Sundancer in Chicago Illinois United States
50ft Sea Ray Sundancer in Chicago Illinois United States
From
1050 USD
1451 views
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Seabird Sailing
United States
Private Couples Weekend Sailing Charter in Chicago Illinois United States
Private Couples Weekend Sailing Charter in Chicago Illinois United States
From
350 USD
1478 views
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Kayak Chicago
United States
Intro to Sea Kayaking in Chicago Illinois United States
Intro to Sea Kayaking in Chicago Illinois United States
From
95 USD
1524 views
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Chicago Boat Rentals
United States
22 FT Private Pontoon Cruise Up to 10 People in Chicago Illinois United States
22 FT Private Pontoon Cruise Up to 10 People in Chicago Illinois United States
From
350 USD
1053 views
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Knot My Boat Charters
United States
Captain Michael Totten in Chicago Illinois United States
Captain Michael Totten in Chicago Illinois United States
From
300 USD
1532 views
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Bobbys Bike Hike
United States
Meet Me Chicago Solos Singles Adventure Club in Chicago Illinois United States
Meet Me Chicago Solos Singles Adventure Club in Chicago Illinois United States
From
69 USD
1187 views
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Angler Charters
United States
Private Charter in Chicago Illinois United States
Private Charter in Chicago Illinois United States
From
1050 USD
1358 views
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Poseidon Chicago Charters
United States
The Chicago River Cruise in Chicago Illinois United States
The Chicago River Cruise in Chicago Illinois United States
From
1200 USD
1355 views
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Knot My Boat Charters
United States
Captain Tanner Ciaramita in Chicago Illinois United States
Captain Tanner Ciaramita in Chicago Illinois United States
From
300 USD
1391 views
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Tall Ship Windy
United States
Independence Day Weekend Kick Off Sail in Chicago Illinois United States
Independence Day Weekend Kick Off Sail in Chicago Illinois United States
From
65 USD
1033 views
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Poseidon Chicago Charters
United States
Day Cruise in Chicago Illinois United States
Day Cruise in Chicago Illinois United States
From
900 USD
1112 views
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Believe Chicago
United States
Chicago Vibes 440 Carver in Chicago Illinois United States
Chicago Vibes 440 Carver in Chicago Illinois United States
From
1223 USD
1493 views
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Chicago Blue Water Charters
United States
Chicago Playpen Anchorage Area in Chicago Illinois United States
Chicago Playpen Anchorage Area in Chicago Illinois United States
From
225 USD
1436 views
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Kayak Chicago
United States
E-Boat Rental in Chicago Illinois United States
E-Boat Rental in Chicago Illinois United States
From
170 USD
1514 views
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Kayak Chicago
United States
Architectural Tour in Chicago Illinois United States
Architectural Tour in Chicago Illinois United States
From
69 USD
1319 views
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Endless Summer Chi
United States
Day Cruise Day Dreamer in Chicago Illinois United States
Day Cruise Day Dreamer in Chicago Illinois United States
From
750 USD
1441 views
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Luxury Jet Cars LLC
United States
Ghost Demon in Chicago Illinois United States
Ghost Demon in Chicago Illinois United States
From
599 USD
1217 views
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Kayak Chicago in
United States
1 Hour Kayak Rentals North Avenue Beach in Chicago Illinois United States
1 Hour Kayak Rentals North Avenue Beach in Chicago Illinois United States
From
35 USD
1532 views
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Kayak Chicago
United States
St Paddy s Day Green River Tour in Chicago Illinois United States
St Paddy s Day Green River Tour in Chicago Illinois United States
From
75 USD
1476 views
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Chicago by Dave
United States
Private Boat Tour in Chicago Illinois United States
Private Boat Tour in Chicago Illinois United States
From
1100 USD
1245 views
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Knot My Boat Charters
United States
72ft Classic Chris Craft in Chicago Illinois United States
72ft Classic Chris Craft in Chicago Illinois United States
From
4000 USD
1214 views
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Luxury Jet Cars LLC
United States
Blaze in Chicago Illinois United States
Blaze in Chicago Illinois United States
From
699 USD
1055 views
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Kayak Chicago
United States
Classic 1950 s Milo Boat Rental in Chicago Illinois United States
Classic 1950 s Milo Boat Rental in Chicago Illinois United States
From
450 USD
1067 views
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Kayak Chicago in
United States
1 Hour Kayak Rentals Chicago River in Chicago Illinois United States
1 Hour Kayak Rentals Chicago River in Chicago Illinois United States
From
30 USD
1054 views
Book now
Seabird Sailing
United States
Air Water Show Private Sailing Charter in Chicago Illinois United States
Air Water Show Private Sailing Charter in Chicago Illinois United States
From
1000 USD
1320 views
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Knot My Boat Charters
United States
57ft Power Catamaran in Chicago Illinois United States
57ft Power Catamaran in Chicago Illinois United States
From
3000 USD
901 views
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Seabird Sailing
United States
Private Weekend Sailing Charter in Chicago Illinois United States
Private Weekend Sailing Charter in Chicago Illinois United States
From
500 USD
1329 views
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Blackhawk Boat Tours LLC
United States
Private Adventure Lake and River Tour in Chicago Illinois United States
Private Adventure Lake and River Tour in Chicago Illinois United States
From
510 USD
1137 views
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Knot My Boat Charters
United States
Captain David Groover in Chicago Illinois United States
Captain David Groover in Chicago Illinois United States
From
300 USD
1566 views
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Kayak Chicago
United States
Lake Shore Skyline Paddle in Chicago Illinois United States
Lake Shore Skyline Paddle in Chicago Illinois United States
From
85 USD
1133 views
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Ace Yachting
United States
Chicago Sunset Fireworks Cruise - Navy Pier in Chicago Illinois United States
Chicago Sunset Fireworks Cruise - Navy Pier in Chicago Illinois United States
From
538 USD
1484 views
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Tall Ship Windy
United States
2026 Air Water Show - Special Event in Chicago Illinois United States
2026 Air Water Show - Special Event in Chicago Illinois United States
From
98 USD
1561 views
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Chicago Blue Water Charters
United States
Lakefront Sightseeing in Chicago Illinois United States
Lakefront Sightseeing in Chicago Illinois United States
From
225 USD
905 views
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Knot My Boat Charters
United States
Capt Dave Krell in Chicago Illinois United States
Capt Dave Krell in Chicago Illinois United States
From
270 USD
1541 views
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Luxury Jet Cars LLC
United States
Barbie World in Chicago Illinois United States
Barbie World in Chicago Illinois United States
From
999 USD
1029 views
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Endless Summer Chi
United States
Fireworks Cruise Day Dreamer in Chicago Illinois United States
Fireworks Cruise Day Dreamer in Chicago Illinois United States
From
900 USD
1464 views
Book now
Kayak Chicago
United States
City Lights Night Paddle in Chicago Illinois United States
City Lights Night Paddle in Chicago Illinois United States
From
69 USD
927 views
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