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Private Jet Charter Flights From Chicago To Anguilla

Chicago → Anguilla

Distance
1,896 nm
Flight Time
4.2 hrs

Fly Private from Chicago to Anguilla

Leave the Windy City behind and land in paradise with Triumph Jets’ private charter service from Chicago to Anguilla. Whether for a winter escape, family vacation, or romantic getaway, this route offers seamless luxury from the Midwest to the Caribbean.
Depart from Chicago Midway (MDW) or Chicago Executive (PWK) and arrive directly at Clayton J. Lloyd International Airport (AXA). Your flight is customized around your schedule, with premium service and total discretion every step of the way.

Estimated Pricing by Aircraft Class

Private charter pricing for this route varies by aircraft size and availability. Contact us for current quotes and availability.

Light Jet
$31,440
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Mid-Size Jet
$39,160
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Super Mid
$40,090
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Heavy Jet
$66,500
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Ultra Long Range
$70,560
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Visiting Anguilla, British Overseas Territory

Pristine beaches and tranquil elegance
Triumph Jets arranges private charter to Anguilla through Clayton J. Lloyd International, the island’s only airport, rebuilt to 5,462 feet and comfortable for turboprops through super-midsize jets with customs on the field. The largest cabins make a choice: careful payload planning into AXA, or the St. Maarten gateway twenty minutes away. Either way, the island’s calm starts at the ramp.

Charter This Route

Get a personalized quote for your private flight from Chicago to Anguilla. Our team will find the perfect aircraft for your needs and budget.

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Frequently Asked Questions

Please refer to the Estimated Pricing by Aircraft Class section above for estimated prices. Final pricing depends on your itinerary, aircraft availability, and operating requirements. Contact Triumph Jets for a personalized quote.

 

Private flights can arrive at Clayton J. Lloyd International Airport (AXA), subject to aircraft suitability and operating conditions. Princess Juliana International Airport (SXM) in St. Maarten is an alternative, with an onward transfer to Anguilla.

 

Top luxury resorts include:

  • Four Seasons Resort & Residences
  • Belmond Cap Juluca
  • Zemi Beach House
  • Aurora Anguilla Resort & Golf Club
  • Frangipani Beach Resort

Highlights include:

  • Meads Bay and Shoal Bay Beach
  • Scilly Cay day trip
  • Snorkeling at Little Bay
  • Sunset sailing charters
  • Fine dining at Blanchards or Veya
  • Private villa experiences