Two Brothers Sailing Adventures
Book now
← All events

Chicago Air and Water Show Boat Charter

Experience one of Chicago’s biggest summer events from Lake Michigan with a private sailboat charter and skyline views.

Check Availability

Private charters from Montrose Harbor. BYOB-friendly. Restroom onboard.

U.S. Navy Blue Angels jets in formation with smoke trails against a blue sky—Chicago Air and Water Show atmosphere

See the Chicago Air and Water Show From the Lake

The Chicago Air and Water Show brings serious summer energy to the lakefront. A private sailboat charter lets your group experience the day from Lake Michigan instead of competing for space along the shoreline.

You still get show-day atmosphere, city views, and open air—but with room to move, drinks and snacks you packed yourself, and a captain handling navigation while traffic and safety zones shift around the event.

Why it's a fit

  • You’re on the water for the show—not elbowing for space on the beach.

  • Room to move, snack, and reset between passes instead of baking on the shoreline.

  • Photos read better from the deck: skyline, lake, and open sky in one frame.

  • Works well for out-of-town guests, families, or anyone who wants the weekend to feel like an event.

  • Boarding is at Montrose Harbor; you get instructions ahead of time so arrival stays simple.

Recommended Charter Options

What to Expect

  1. Meet at Montrose Harbor

    Arrive at the harbor and meet your captain near the boarding location.

  2. Board the boat and get settled

    Step aboard, get settled, and store your drinks, snacks, and belongings.

  3. Review a short safety briefing

    Your captain will review basic safety information before leaving the dock.

  4. Cruise Lake Michigan during the event window

    Sail during the event window with routes shaped by safety zones, lake traffic, and captain discretion.

  5. Enjoy skyline, lakefront, and show-day atmosphere

    Enjoy lake-level views while show-day activity unfolds along the shore.

  6. Return to the same dock

    Your charter ends back at the original boarding location.

Planning Tips

  • Book early—Air and Water Show dates are high demand on the lake.

  • Bring layers; the lake often feels cooler than the sidewalk.

  • Pack drinks, snacks, sunscreen, and charged phones.

  • Expect heavier lake traffic than a typical charter day.

  • Routes and viewing areas depend on safety zones, conditions, and captain discretion.

What's Included

  • Private use of the sailboat

  • Experienced captain / captain arrangement

  • Safety briefing before departure

  • Required safety gear onboard

  • Restroom onboard

  • Cooler/storage space

  • Boarding instructions before your trip

  • Weather monitoring before departure

Good to Know

Air and Water Show routes, timing, and viewing areas may vary based on lake traffic, weather, event operations, safety zones, and captain discretion. The charter delivers a private Lake Michigan experience during the event, but exact show visibility can vary.

FAQ

Is this a private charter?
Yes. Your charter is private for your group.
Where do we board?
You will board at Montrose Harbor in Chicago. Detailed instructions are sent before your charter.
Is show visibility guaranteed?
Visibility can vary based on weather, lake traffic, safety zones, and event operations. The charter is planned around the event atmosphere from Lake Michigan.
Can we bring food and drinks?
Yes. BYOB and light food are welcome.
Is there a bathroom onboard?
Yes. There is a restroom onboard.

Ready for the Chicago Air and Water Show?

Book a private Lake Michigan charter and experience one of Chicago’s biggest summer events from the water.

Check Availability