Corporate Transportation RFP Checklist for Chicago Travel Managers and Executive Assistants

Most ground transportation sourcing goes wrong the same way. A buyer collects three or four proposals, compares hourly rates and airport transfer prices, takes the lowest number, and spends six months discovering that price was the least important thing on the page.

A chauffeured transportation agreement is not a purchase of vehicle time. It is a purchase of reservation control, dispatch response, airport execution, billing accuracy, data handling, and accountability when something goes wrong at 6:40 a.m. on the way to a board meeting. Those capabilities are either specified in the RFP or negotiated later, one incident at a time, from a weaker position.

This checklist is for the people who own that outcome: travel managers, procurement leads, executive assistants and office managers who book for others, meeting planners, and the finance and risk stakeholders who inherit the invoices. It is deliberately vendor-neutral. Use it to evaluate any provider — including the one that published it.

Before You Write the RFP: Separate Mandatory From Scored

A usable RFP has two distinct layers, and mixing them is the most common structural error.

The first layer is pass/fail documentation. Licensing, insurance certificates, and regulatory compliance are not preferences to be weighed against a competitive rate. Either the documents are current and complete, or the response does not advance. Scoring compliance lets a well-written proposal compensate for a missing certificate — exactly what your risk team is trying to prevent.

The second layer is the weighted scorecard — operations, service design, reporting, coverage, and cost. That is where judgment belongs.

For independent context, the Global Business Travel Association maintains business travel RFP templates and sourcing toolkits, and has published ground transportation strategy guidance with the Institute of Travel Management. These are neutral industry resources worth reviewing alongside this checklist; they imply no endorsement of any provider.

1. Define Program Scope Before You Ask for Pricing

You cannot compare proposals against a scope you have not written. Before the RFP goes out, document:

• Primary and secondary markets, and which airports are in scope
• Approximate annual trip volume, with peak periods and seasonality
• Traveler categories — executives, staff, candidates, clients, board members, guests
• Trip types: point-to-point, hourly and as-directed, roadshows, multi-stop, long-distance
• Group movements, meetings, and convention transportation planning requirements
• Accessibility and mobility needs, child seats, recurring special equipment
• After-hours and early-morning demand, where service models most often diverge

Scope also determines who scores what. If assistants do most of the booking, they should evaluate the reservation and change-management sections. Finance scores billing and reporting. Risk holds the pass/fail gate.

2. Licensing, Insurance, and Mandatory Risk Documentation

Require documents, not assurances. Ask each respondent to supply:

• Current operating authority and licensing for every market served directly
• Certificates of insurance naming required coverages, with your organization as certificate holder where appropriate
• Chauffeur screening: background checks, motor vehicle records, drug and alcohol policy, training program
• Vehicle inspection, maintenance, and fleet-age policies
• Incident reporting procedure, including notification timelines and who is contacted
• Written disclosure of any subcontractor or affiliate used, and in which markets

That last item is where most programs are underspecified. A provider may operate its own vehicles in one market and coordinate independent operators elsewhere — a normal and often necessary model. But it must be disclosed, and contractual responsibility for affiliate-delivered service stated in writing rather than assumed.

3. Reservations, Authorized Bookers, and Confirmations

Booking channels and required fields

Ask how reservations are accepted — phone, email, web, or integration with your booking tool — and which channels support the full feature set. Some accept web bookings but cannot handle multi-stop or hourly itineraries there.

Specify required booking fields: passenger name and mobile number, booker name, cost center code, project or matter number, flight details, passenger and luggage counts, and special requirements.

Authorization and approval controls

Define who may book, who may approve, and what spending or vehicle-class limits apply. A provider should maintain your authorized booker list, apply account rules consistently, and flag reservations that fall outside them.

Confirmation and change control

Confirmations should be addressable to the booker, the passenger, or both. An assistant booking for six executives needs the record even when the passenger receives the pickup details.

Ask how changes are submitted, acknowledged, and reconfirmed, and what audit trail exists. Then ask the same about cancellation windows and no-show definitions.

4. Dispatch, Escalation, and Service Recovery

This section separates providers more reliably than any other.

• What hours are reservation and dispatch staff reachable by live phone, and what happens outside them?
• Is there a named escalation path, and how far up does it go?
• When a vehicle is delayed, who is notified — passenger, booker, or both — and how?
• How are changes communicated to the chauffeur while a trip is active?
• What is the documented service recovery process, and does it produce a written incident summary?

Two cautions. Response-time commitments that appear in a proposal but not in the contract are marketing; if a number matters, require it as a contractual service level with a defined measurement method. And a claim that a replacement vehicle is always standing by is rarely true across every market and hour. The better question is what happens when none is available, and how quickly you find out.

5. Airport and Flight Operations

Airport execution generates the most complaints in most corporate programs, and nearly all of it is procedural.

• Are airport legs associated with flight details so arrival timing can be monitored and pickup coordinated?
• What differs in procedure and cost between curbside pickup and meet-and-greet inside the terminal?
• What grace periods apply to domestic and international arrivals, and how is wait time charged after that?
• How are terminal changes and early arrivals handled?
• What instructions does the passenger receive, when, and what if they cannot locate the vehicle?
• How are private aviation and FBO pickups handled, if relevant?

Ask respondents to describe their airport transportation procedures in writing rather than answering yes to a capability question. The written procedure reveals whether a process exists or is improvised.

6. Vehicle Categories and Capacity Controls

Define categories in the RFP so responses are comparable. One provider’s “large SUV” may not match another’s.

• How are sedan, SUV, and Sprinter categories defined, and what is the practical capacity of each once luggage is counted?
• Practical luggage capacity is routinely lower than advertised seating. Require both numbers.
• Can a specific make or model be requested, and when is a comparable vehicle substituted?
• What is the substitution policy, and is the client notified before the trip?
• How are child seats, accessible vehicles, and oversized equipment arranged, and how far ahead?
• For multi-vehicle moves, how is the manifest built and group transportation sequenced across pickups?

Ask providers to explain vehicle categories and practical capacity against a real scenario from your own travel — six passengers with checked luggage — rather than in the abstract.

7. Service Levels and KPIs That Mean Something

Many transportation KPIs are unmeasurable as written. Insist on metrics with a defined data source, measurement window, and agreed exception list.

Metrics that tend to hold up:

• On-time arrival at pickup, against the reserved time with a defined tolerance
• Reservation accuracy — trips performed as confirmed, without vehicle-class or timing errors
• Confirmed reservations completed as booked, with unfulfilled trips reported by cause
• Response time to reservation and change requests during staffed hours
• Billing accuracy, as the share of invoice lines disputed or adjusted
• Complaint volume and resolution time, by category

Agree in advance how each is calculated and who produces the data. A KPI the provider self-reports with no defined method is a talking point, not a service level.

8. Full Fee Disclosure and Comparable Pricing

Rate comparison is meaningless without a complete fee schedule. Have every respondent price the same standardized scenarios — your five or six most common trips, with exact addresses, times, passenger and luggage counts — and submit an ancillary fee schedule covering at minimum:

• Base rates by vehicle category and service type, plus hourly minimums
• Wait time policy, grace periods, and billing increments
• Additional stops, out-of-area, and extended mileage charges
• Gratuity: included, suggested, or discretionary, and whether applied automatically
• Fuel, surcharge, or administrative fees
• Late-night, holiday, and peak-period differentials
• Meet-and-greet, parking, tolls, and airport access fees
• Cancellation and no-show terms by service type
• Incidentals, cleaning fees, and how they are documented

Require assumptions and exceptions to be stated separately from negotiated rates. A rate card without its assumptions is not a price. Route, timing, vehicle category, stops, wait time, and service type all shape transportation rates and pricing factors — check how each provider explains its own variables before comparing totals.

9. Billing, Data, and Reporting

Finance stakeholders should score this section, because they will live with it.

• What does a trip-level invoice line contain — date, passenger, booker, pickup and drop-off, vehicle category, base rate, and each fee itemized?
• Can charges be allocated to cost centers, departments, projects, or matter numbers captured at booking?
• What billing arrangements are available, including account terms or a card on file, and what is confirmed at account setup?
• What is the dispute workflow and resolution window, and how are credits documented?
• What standard reports are produced, how often, and in what export formats?
• What is the retention period, and can historical trip data be exported if the relationship ends?

That last question matters more than it appears. Trip history is your data. Confirm you can take it with you.

10. Traveler Data, Privacy, and Duty of Care

Ground transportation providers hold traveler names, mobile numbers, home addresses, flight itineraries, and payment credentials. Treat that accordingly.

• Who can access traveler profiles and trip history, and how is that access controlled?
• How is payment information stored and processed, and what card-security standards apply?
• What is shared with affiliate operators, and is it limited to what the trip requires?
• What is the retention and deletion policy, and does it match the published privacy policy?
• For duty of care: how is an incident escalated, who is notified, and how quickly?
• Can records be produced when you need to locate a traveler during a disruption?
• What additional handling applies to executive or higher-risk travel, including discretion?

Ask for the privacy policy and read it against the answers. Where the two disagree, the policy is the commitment.

11. Affiliates, Subcontractors, and Multi-City Coverage

Almost every provider fulfills some service through independent operators. The question is never whether affiliates are used, but how they are governed.

• Who holds the contract with the local operator, and who is responsible for performance?
• How are operator licensing, insurance, and vehicle standards verified before a market is used, and how often re-verified?
• How is vehicle class mapped across markets, given that models and configurations vary?
• Airport procedures, meet-and-greet practices, tolls, parking, and gratuity conventions differ by city. Who confirms them per leg?
• Who owns traveler communication in an affiliate market, and how are changes escalated?
• Is billing consolidated, in what currency, and how are exchange rates and local fees applied?

Where a program includes multi-city chauffeured transportation, require a written description of the coordination model rather than a coverage map. A city list tells you where a provider can arrange service. It does not tell you who answers the phone when a flight into an unfamiliar market lands three hours late.

12. Implementation, Account Setup, and Performance Reviews

An award is the beginning of the work, not the end.

• Structure a pilot with defined scope, duration, and evaluation criteria before full rollout
• Confirm account setup: booker lists, profiles, cost center codes, approval rules, billing configuration
• Require a training and communication plan for bookers and travelers
• Set the reporting cadence and first review date at signature, not later
• Define corrective action: what triggers a formal performance discussion, what remediation contains, on what timeline
• Agree renewal and termination provisions, including notice periods and transition assistance

Schedule quarterly reviews for the first year. Programs drift quietly, and the review is where drift becomes visible while it is still cheap to correct.

A Weighted Scorecard You Should Adjust

Scoring imposes discipline on a decision that otherwise defaults to price. The weighting below is a starting point, not a standard. An airport-heavy program should weight operations higher; a regulated organization should weight compliance and data handling higher; a cost-constrained program may legitimately weight price above the example shown. Set your weights before you read the responses.

Score against evidence in the response, not against how well the response is written.

Red Flags in Vendor Responses

• Capability confirmed without procedure — “yes, we monitor flights,” with no account of what happens when one changes
• A rate card with no ancillary fee schedule, or fees described as case by case
• Reluctance to disclose which markets are served by affiliates or subcontractors
• No named escalation path beyond a general phone number
• Service commitments stated in marketing language but absent from the contract
• Insurance described in general terms without certificates
• Reporting available on request rather than as a defined deliverable
• No answer on who owns your trip data or how it is exported
• Pricing materially below every other respondent with no structural explanation

A low score in one area is not disqualifying. A pattern of unwillingness to put operational detail in writing usually is.

About the Source of This Checklist

This checklist was published by a transportation provider, which you should factor into how you read it. In the interest of the transparency it asks of vendors:

LimoRSVP has provided chauffeured transportation since 2004 from a Chicago operating base. Active reservations are supported by live reservation and dispatch support; itinerary changes are made through the office, and dispatch updates the chauffeur. Vehicles used for service are fully insured, and chauffeurs are licensed in the operating jurisdiction. Accounts can support multiple authorized bookers through one office point of contact, with confirmations sent to the booker rather than only the passenger. Airport legs can be associated with flight details for monitoring and pickup coordination. Outside its Chicago operating market, LimoRSVP coordinates service in more than 500 cities through local affiliate operators.

That is a description, not a score. Apply these questions to us as you would to any respondent.

Putting the Checklist to Work

A structured RFP does not necessarily produce a better price. It produces a comparable one, and surfaces the operational gaps that would otherwise surface during your first travel disruption.

Write the scope first. Hold compliance as a pass/fail gate. Score everything else against evidence. Plan implementation and the first review before signing.

If you are building or renewing a program and want to work through scope, service levels, and reporting requirements against a real itinerary, we are glad to discuss it — whether you are evaluating an ongoing Chicago corporate transportation program or starting with a single trip. Call 312-208-7354 or request a quote with your program details.

Last reviewed: August 6, 2026. Service policies, insurance requirements, and airport procedures change; verify current details with any provider before contracting.