The Loop

Service area

The Loop

The Chicago Loop is the engine of the city’s commercial life: the addresses on LaSalle, the law firms stacked above the river, the trading floors, the convention hotels, the courthouses. It is a place where time is measured in meetings and delays are measured in consequences. Second City Livery was designed precisely for this environment.

• Loop to O’Hare (ORD) — Approximately 35–50 minutes depending on time of day
• Loop to Midway (MDW) — Approximately 20–30 minutes
• Flight tracking — Real-time monitoring adjusts staging automatically on every run
• Early morning departures — Pre-dawn Loop hotel pickups handled as standard operations