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Departure
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| Flight | To | Terminal | Departure | expected | A/C | Info | Status | |||
| MDW 7048 | Orlando International (MCO) | T1 | 01:50 | 752 | NOW BOARDING | |||||
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EAS 123 | New York (JFK) | T1 | 01:55 | 752 | ||||
| CRB 1134 | Panama City (PTY) | T1 | 03:25 | M82 | ||||||
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CO 1163 | Port of Spain (POS) | T1 | 03:40 | M81 | |||||
| MDW 7060 | Houston (IAH) | T1 | 04:15 | 752 | ||||||
| MB 648 | Little Rock (LIT) | T1 | 05:10 | M81 | ||||||
| MDW 4909 | Chicago Midway (MDW) | T1 | 05:55 | 752 | ||||||
| MDW 7400 | Panama City (PTY) | T1 | 06:00 | 733 | ||||||
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AC 1627 | Toronto Pearson (YYZ) | T1 | 06:00 | 733 | |||||
| CCA 164 | Toronto Pearson (YYZ) | T1 | 07:00 | M81 | ||||||
| CRB 1114 | Santo Domingo Las Americas (SDQ) | T1 | 07:15 | M82 | ||||||
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ASX 236 | New York (JFK) | T1 | 07:47 | 752 | |||||
| CRB 626 | Baltimore (BWI) | T1 | 07:55 | 752 | ||||||
| CRB 958 | Miami International (MIA) | T1 | 09:45 | M82 | ||||||
| MDW 7202 | Bridgetown (BGI) | T1 | 10:00 | 141 | ||||||
| MDW 7002 | Atlanta (ATL) | T1 | 10:00 | 752 | ||||||
| AWA 34 | Philadelphia (PHL) | T1 | 10:17 | 72S | ||||||
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TT1 2036 | New York (JFK) | T1 | 10:35 | M82 | |||||
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TT1 2604 | Newark (EWR) | T1 | 10:45 | 73S | |||||
| CRB 1182 | Punta Cana (PUJ) | T1 | 11:35 | M83 | ||||||