Chicago Boating Guides, Events & Boat Rental Tips

Insider guides to renting, captaining, and getting the most out of Chicago's waterways, written by the team that runs the boats. Start with what a charter costs, read up on hiring a captain, or plan around the summer's biggest boating events.

Browse the archive Check availability
Aerial view of Burnham Harbor and Soldier Field with the Chicago skyline and Lake Michigan
Burnham Harbor and Soldier Field, Chicago
In the archive
11 posts
Five-star reviews
1071+
Active in the fleet
23 yachts
Home port
31st Street Harbor

Read up before you head out.

11 posts

  1. Chicago Boat Rental Prices & Costs

    Updated October 10, 2026 · 7 min

    How much does it cost to rent a boat in Chicago? Compare pricing by boat size, trip length and group size, plus captain, party boat and membership costs.

    Read

  2. Chicago Boat Events & Boating Calendar

    Updated October 8, 2026 · 6 min

    Navy Pier fireworks nights, holiday weekends, the Air & Water Show, and a month-by-month Chicago boating calendar.

    Read

  3. Chicago Boat Captains for Hire: Cost, Rules & What to Expect

    Updated October 9, 2026 · 8 min

    What a captain costs for a Chicago boat rental, how to book one, bareboat captain rules, gratuity, and what your captain handles on the water.

    Read

  4. Chicago Boat Rental Requirements, Rules & Guidelines

    October 13, 2026 · 7 min

    Do you need a boating license? Passenger limits, captains, alcohol, food, swimming, weather and cancellation rules for renting a boat in Chicago.

    Read

  5. The Ultimate Bachelor and Bachelorette Party Yacht Guide

    Updated October 16, 2026 · 10 min

    How to plan a bachelor or bachelorette party on a Chicago yacht: guest count, choosing the right boat, timing, food and drinks, what to wear, and how to book.

    Read

  6. 4th of July Boat Rentals in Chicago

    Updated October 12, 2026 · 7 min

    Where to watch the fireworks from a boat, when to book, what boats fit your group and what July 4th on the water costs.

    Read

  7. Memorial Day Boat Rentals in Chicago

    Updated October 15, 2026 · 7 min

    Where to go boating Memorial Day Weekend, when to book, which boats fit your group, party ideas and what to bring.

    Read

  8. Chicago Boat Rental Guide: Prices, Rules & Where to Go

    Updated October 11, 2026 · 9 min

    Do you need a license, what does it cost, is a captain included and where can you go? What to know before renting a boat in Chicago.

    Read

  9. How Much Does a Boat Club Membership Cost in Chicago?

    Updated October 14, 2026 · 7 min

    Chicago boat club membership costs, what's included, and how membership compares with boat ownership and individual rentals.

    Read

  10. Father's Day Boat Rentals in Chicago

    Updated October 16, 2026 · 5 min

    Plan Father's Day on a private Chicago boat: choosing a boat for your group, itinerary ideas and what to book in advance.

    Read

  11. Labor Day Weekend Boat Rentals in Chicago

    Updated October 17, 2026 · 5 min

    Spend Labor Day weekend on Lake Michigan: boating ideas, popular destinations, boats by group size and booking tips.

    Read

Reading is just
the beginning.

Skyline cruises, Playpen afternoons, fireworks after dark.
Where will your day take you?

The Fleet ↗Experiences ↗Memberships ↗