Casino Charter Flights from Chicago, IL

Fly to top casino destinations on comped charter and commercial flights departing Chicago O'Hare International Airport (ORD). Grueninger Gold is your independent casino host — we arrange flights, hotel, and transfers for qualified players from Chicago. Charter flights are operated by Sun Country Airlines. Browse upcoming Chicago departures below. Contact us to see if you qualify.

Upcoming trips from Chicago (7)

Charter flight

Charter flight

Depart

Chicago O'Hare International Airport (ORD)

Illinois

Destination

Laughlin, NV

Harrah's - Laughlin

Depart

8/15/26

Sat

Return

8/19/26

Wed

(Sat) 8/15/26 to (Wed) 8/19/26

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Official Caesars Rewards Charter

Commercial flight

Commercial flight

Depart

Chicago O'Hare International Airport (ORD)

Illinois

Destination

Las Vegas, NV

Paris - Las Vegas

Depart

9/1/26

Tue

Return

9/5/26

Sat

(Tue) 9/1/26 to (Sat) 9/5/26

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Official Caesars Rewards Commercial Flight

Charter flight

Charter flight

Depart

Chicago O'Hare International Airport (ORD)

Illinois

Destination

Biloxi, MS

Harrah's - Gulf Coast

Depart

9/8/26

Tue

Return

9/11/26

Fri

(Tue) 9/8/26 to (Fri) 9/11/26

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Official Caesars Rewards Charter

Charter flight

Charter flight

Depart

Chicago O'Hare International Airport (ORD)

Illinois

Destination

Reno, NV / Tahoe, CA

Eldorado - Reno, Harrah's - Lake Tahoe, Caesars Republic - Lake Tahoe, Silver Legacy - Reno

Depart

9/30/26

Wed

Return

10/4/26

Sun

(Wed) 9/30/26 to (Sun) 10/4/26

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Official Caesars Rewards Charter

Commercial flight

Commercial flight

Depart

Chicago O'Hare International Airport (ORD)

Illinois

Destination

Rincon, CA

Harrah's - Southern California

Depart

10/16/26

Fri

Return

10/20/26

Tue

(Fri) 10/16/26 to (Tue) 10/20/26

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Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago O'Hare International Airport (ORD)

Illinois

Destination

Rincon, CA

Harrah's - Southern California

Depart

10/16/26

Fri

Return

10/20/26

Tue

(Fri) 10/16/26 to (Tue) 10/20/26

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Official Caesars Rewards Commercial Flight

Charter flight

Charter flight

Depart

Chicago O'Hare International Airport (ORD)

Illinois

Destination

Laughlin, NV

Harrah's - Laughlin

Depart

10/29/26

Thu

Return

11/2/26

Mon

(Thu) 10/29/26 to (Mon) 11/2/26

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Official Caesars Rewards Charter