Where pickups start. Chicago requests most often begin in River North, Wrigleyville / Lakeview, Lincoln Park and West Loop. Give the dispatcher a street address or a named lot entrance, not just the neighborhood—drive time, staging, and the vehicle's approach all depend on the exact curb.
Where groups go. Destinations named for Chicago include Wrigley Field, Soldier Field, United Center, Grant Park / Millennium Park and Navy Pier. Each has its own loading rules; ask the venue where a bus or limo can wait, and agree on a meeting corner in case the curb is blocked when the group comes out.
Dates that fill first. Local calendars around Lollapalooza, Taste of Chicago, Chicago Air & Water Show and St. Patrick's Day Parade & river dyeing concentrate demand on a handful of weekends. Those dates are worth quoting early; confirm the current schedule with the organizer, since this list is not a live calendar.
Itineraries groups ask about. River North bar crawl; Wrigleyville pub crawl; West Loop restaurant tour; Suburb-to-downtown Saturday night run. Share your version with every stop in order and an honest end time so the quote covers the whole block.
Airport groups. Chicago trips connect to ORD, MDW. Provide flight numbers, terminal, bag counts, and one group contact; the driver meets at the commercial-vehicle zone, which is usually not the passenger curb.
Beyond Chicago. Trips that continue into Arlington Heights, Aurora, Berwyn or Bloomington are quoted as one itinerary. The Illinois guide covers statewide staging and long-distance planning.