After-Hours Client Entertainment: Chicago Executive Transportation Guide
How should I arrange transportation for client entertainment in Chicago?
Book hourly executive car service rather than point-to-point rides. The driver picks up your client at their hotel, drives to the restaurant or venue, waits during the event, and handles any additional stops. For multi-venue evenings, book 4-6 hours of dedicated service with a premium vehicle like a Mercedes S-Class or Escalade.
Client entertainment is where business relationships are built. The restaurant, the conversation, the wine selection all matter. But the transportation that frames the evening matters just as much. Arriving in a premium vehicle with a professional chauffeur sets the tone before you sit down, and a seamless return to the hotel closes the evening with the same polish.
Planning the Client Entertainment Itinerary
A well-planned evening eliminates logistical friction so you can focus entirely on your client. Here is a typical multi-stop client entertainment itinerary with transportation timing:
| Time | Activity | Transportation |
|---|---|---|
| 6:00 PM | Pick up client at hotel | Driver at lobby entrance |
| 6:15 PM | Pick up host | Second stop at your office or home |
| 6:45 PM | Arrive at restaurant | Drop-off at door, driver waits |
| 9:30 PM | Depart restaurant | Car positioned at entrance |
| 9:45 PM | Optional: cocktail bar | Short drive, driver waits |
| 11:00 PM | Return client to hotel | Door-to-door, then host home |
Top Chicago Restaurants for Client Entertainment
These are the restaurants Chicago executives consistently choose for client dinners, along with transportation logistics for each:
- Alinea (Lincoln Park): 20-minute drive from Mag Mile. Valet available. 3-hour tasting menu means your driver waits approximately 3.5 hours. Perfect for closing major deals.
- Chicago Cut Steakhouse (River North): 5-10 minutes from most downtown hotels. Ideal for classic power dinners. 90-minute to 2-hour typical duration.
- RPM Italian (River North): High-energy atmosphere. Popular with media and finance executives. Book the private dining room for confidential discussions.
- Girl & The Goat (West Loop): Fulton Market destination. 15 minutes from Loop hotels. Creative menu impresses food-oriented clients.
- Gibsons Bar (Gold Coast): Chicago institution for steak and networking. Easy Mag Mile access. Often selected for relationship-building dinners.
Hourly Service vs. Point-to-Point for Entertainment
For client entertainment, hourly service is almost always the better choice:
- Flexibility: Dinner runs long, you decide to add a stop, or the client wants to visit a second venue. The car is there.
- Availability: Late-night rideshare can be scarce or surge-priced. Your car is guaranteed regardless of time.
- Impression: The same driver in the same vehicle for the entire evening projects consistency and planning.
- Safety: After drinks, professional transportation eliminates any concern about driving.
Budget Tip: A 5-hour evening of hourly service typically costs less than booking four separate point-to-point rides, especially when factoring in late-night rideshare surge pricing and the time spent coordinating each pickup.
Communication Etiquette with Your Driver
Seamless coordination with your chauffeur ensures the evening runs smoothly without visible logistics:
- Text "10 min" before departing: This gives the driver time to pull up to the entrance.
- Text new destinations: If plans change, a quick text with the new address is all that is needed.
- Confirm drop-off order: If the evening involves multiple passengers, text the driver the drop-off sequence so the ride flows naturally.
- No need to announce logistics: Never discuss car logistics in front of clients. Handle everything via text so the experience feels effortless.
For more corporate travel etiquette, see our Corporate Travel Etiquette Guide and VIP Client Transportation Guide.
Frequently Asked Questions
How do I book car service for a client dinner in Chicago?
Book an executive sedan or SUV with hourly service rather than a point-to-point trip. Provide the restaurant name, reservation time, and hotel for return. The driver picks up your client at their hotel, waits during dinner, and returns them afterward. For multi-stop evenings, book 4-6 hours of dedicated service.
Should the car wait during a client dinner?
Yes. Having the car wait provides seamless service without rebooking. When dinner ends, the car is immediately available whether that is 90 minutes or 3 hours later. Most services charge an hourly wait rate that is lower than the driving rate. This also ensures availability late at night when rideshare supply drops.
What is the best vehicle for client entertainment in Chicago?
For 1-2 clients, a Mercedes S-Class makes the strongest impression. For groups of 3-5, a Cadillac Escalade or Lincoln Navigator provides luxury with conversation space. For large client groups of 6-12, a Mercedes Sprinter with executive seating allows continued conversation between venues.
Book Client Entertainment Transportation
Hourly service with premium vehicles for flawless client evenings. Let us handle the logistics while you focus on the relationship.