Casino Charter Flights from Chicago, IL

Fly to top casino destinations on comped charter and commercial flights departing Chicago Midway International Airport (MDW). 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 (18)

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

11/8/26

Sun

Return

11/13/26

Fri

(Sun) 11/8/26 to (Fri) 11/13/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

11/11/26

Wed

Return

11/16/26

Mon

(Wed) 11/11/26 to (Mon) 11/16/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

11/15/26

Sun

Return

11/20/26

Fri

(Sun) 11/15/26 to (Fri) 11/20/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

11/18/26

Wed

Return

11/23/26

Mon

(Wed) 11/18/26 to (Mon) 11/23/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

11/19/26

Thu

Return

11/24/26

Tue

(Thu) 11/19/26 to (Tue) 11/24/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

11/25/26

Wed

Return

11/30/26

Mon

(Wed) 11/25/26 to (Mon) 11/30/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

12/2/26

Wed

Return

12/7/26

Mon

(Wed) 12/2/26 to (Mon) 12/7/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Las Vegas, NV

Paris - Las Vegas

Depart

12/5/26

Sat

Return

12/9/26

Wed

(Sat) 12/5/26 to (Wed) 12/9/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

12/6/26

Sun

Return

12/11/26

Fri

(Sun) 12/6/26 to (Fri) 12/11/26

View Trip

Official Caesars Rewards Commercial Flight

Charter flight

Charter flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Biloxi, MS

Beau Rivage

Depart

12/8/26

Tue

Return

12/12/26

Sat

(Tue) 12/8/26 to (Sat) 12/12/26

View Trip

Official MGM Air Charter

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

12/9/26

Wed

Return

12/14/26

Mon

(Wed) 12/9/26 to (Mon) 12/14/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

12/10/26

Thu

Return

12/15/26

Tue

(Thu) 12/10/26 to (Tue) 12/15/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

New Orleans, LA

Caesars - New Orleans

Depart

12/11/26

Fri

Return

12/14/26

Mon

(Fri) 12/11/26 to (Mon) 12/14/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

12/13/26

Sun

Return

12/18/26

Fri

(Sun) 12/13/26 to (Fri) 12/18/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

12/16/26

Wed

Return

12/21/26

Mon

(Wed) 12/16/26 to (Mon) 12/21/26

View Trip

Official Caesars Rewards Commercial Flight

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Reno, NV / Tahoe, CA

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

Depart

12/17/26

Thu

Return

12/22/26

Tue

(Thu) 12/17/26 to (Tue) 12/22/26

View Trip

Official Caesars Rewards Commercial Flight

Charter flight

Charter flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Biloxi, MS

Beau Rivage

Depart

1/16/27

Sat

Return

1/20/27

Wed

(Sat) 1/16/27 to (Wed) 1/20/27

View Trip

Official MGM Air Charter

Commercial flight

Commercial flight

Depart

Chicago Midway International Airport (MDW)

Illinois

Destination

Las Vegas, NV

Paris - Las Vegas

Depart

2/13/27

Sat

Return

2/17/27

Wed

(Sat) 2/13/27 to (Wed) 2/17/27

View Trip

Official Caesars Rewards Commercial Flight