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Enterprises
Chicago Airways
| Enterprise | Headquarters | Country | Business relations |
|---|---|---|---|
| Aircraft Trade and Leasing Organization (ATO) | Toronto Pearson (YYZ) |  |
Lessor |
| Bluebonnet Air (BB) | Houston (IAH) |  |
Interlining |
| emAIR (EM) | Chicago O'Hare (ORD) | |
Interlining |