
Cadillac Escalade
The default choice for Chicago executive travel. Commanding presence, a cabin quiet enough for a call on the Kennedy, and enough room for six with luggage.

Loop · West Loop · Fulton Market
Executive transportation for the firms that run Chicago. Roadshows, client dinners, board offsites and airport runs, all on one account with one invoice at month end.
Corporate chauffeur service in Chicago is judged on one thing: whether the car is at the door when the meeting ends. We build every corporate account around that, from a single Wacker Drive to O'Hare run to a three-day investor roadshow with eleven stops between the Loop, Fulton Market and Oak Brook.
Chicago's business geography is unusually spread out. Trading and law live on LaSalle and Wacker. Consulting and tech have migrated west to Fulton Market and the West Loop. Manufacturing and pharma headquarters sit out along the Tri-State in Deerfield, Lake Forest and Oak Brook. Conventions land at McCormick Place. A chauffeur who understands those corridors saves your team the twenty minutes that a navigation app will not.
Built for Business Travel
Ground transportation that behaves like a vendor your finance team is happy to keep.
One invoice covering every ride, every rider, every cost center. Trip-level detail for expense allocation, no employees fronting cash and chasing receipts.
Executives who ride weekly are matched with the same chauffeurs. They learn the route, the coffee order and which door of 300 N LaSalle you actually use.
Account holders are dispatched first. When a February storm compresses supply across Chicagoland, your team is covered before the open market.
Chauffeurs sign confidentiality agreements. Calls taken in the back seat stay in the back seat. Partition available on request in the Sprinter.
Multi-stop days planned in advance with staging, standby and rolling waits. Your chauffeur holds the car; you do not rebook between meetings.
Certificates of insurance, W-9, chauffeur licensing and vehicle inspection records supplied on request for procurement review.
How It Works
Corporate onboarding is deliberately unbureaucratic.
Rough monthly trip count, which offices, which airports, how many travelers need booking authority. Five minutes on the phone is usually enough.
Rate card, certificate of insurance, W-9 and a short account agreement. Procurement gets everything it needs in one packet, not five emails.
Executive assistants and travel managers get direct dispatch access. Rides can be booked by email or online against the account.
Every trip lands on one monthly invoice with rider, date, route and cost center. Your AP team touches it once.
River North · ChicagoChicago Corridors
A 9 AM at 233 S Wacker, an 11 AM in Fulton Market, lunch at Gibsons on Rush, then a 3 PM in Oak Brook and a 6:40 out of O'Hare. That is a normal Chicago day, and it is four different traffic problems stitched together.
Our chauffeurs stage rather than circle. Between meetings the car waits nearby, the driver is reachable by text, and departure happens the moment you walk out. On a roadshow, that alone recovers an hour across a day.
For convention travel, McCormick Place is a category unto itself. Three connected buildings, four halls and 2.6 million square feet of exhibit space, with an arrival geometry that punishes anybody who has not done it before. Sprinter vans keep a delegation together and drop at the right entrance.
The Fleet
Black, late-model, immaculate. Escalades and Navigators for principals, Sprinters for teams.

The default choice for Chicago executive travel. Commanding presence, a cabin quiet enough for a call on the Kennedy, and enough room for six with luggage.

Understated and lounge-smooth. Reclining second-row captain's chairs make it the quiet favorite for long Loop-to-suburb runs.

Extended wheelbase, real third-row legroom and the deepest cargo hold in the SUV tier. Built for airport runs where nobody holds a bag on their lap.

The value pick. Same seven seats, same chauffeur, same flat rate, a little less badge. Popular with families flying out of Midway.

Stand-up cabin, executive seating and luggage racks. One vehicle instead of three for board offsites, wedding parties and convention groups.

The occasion car. Wraparound leather, fiber-optic lighting and a bar console for weddings, prom and Chicago nights that deserve an entrance.
Starting prices in USD before taxes and gratuity. Your final flat rate depends on route, date, hours and vehicle. Each vehicle is shown with and without a professional chauffeur.
Pricing
Hourly as-directed or flat point-to-point. Account holders receive tiered volume pricing.
| Vehicle | Class and Capacity | Starting Rate |
|---|---|---|
| Ford Expedition | Luxury SUV, up to 7 | from $90/hr |
| GMC Yukon XL | Extended SUV, up to 7 | from $92/hr |
| Lincoln Navigator | Luxury SUV, up to 6 | from $95/hr |
| Cadillac Escalade | Flagship SUV, up to 6 | from $95/hr |
| Mercedes-Benz Sprinter Van | Group van, up to 14 | from $140/hr |
| Lincoln Stretch Limousine | Occasions, up to 10 | from $140/hr |
Starting prices in USD, quoted flat before Illinois taxes and gratuity. Final pricing depends on route, date, vehicle class and total hours. Hourly charters carry a minimum booking; the stretch limousine is hourly only. Confirm your exact rate by requesting a quote online.
| Route | Detail | Starting Rate |
|---|---|---|
| Loop to O'Hare (ORD) | Executive SUV | from $95 |
| Loop to Midway (MDW) | Executive SUV | from $95 |
| Loop to McCormick Place | Convention transfer | from $90 |
| Loop to Oak Brook | Corporate corridor | from $110 |
| Loop to Rosemont and Donald E. Stephens | Convention transfer | from $110 |
| Loop to Deerfield or Lake Forest | North Shore campuses | from $135 |
Corporate accounts receive volume-tiered pricing off these starting rates. Request a rate card online.
Roadshows and Client Entertainment
Investor roadshows, due diligence tours, client dinners at Alinea or RPM Steak, board offsites in Lake Forest. We plan the day with your assistant, stage the vehicles, and hold them through the last handshake.
Where Chicago Business Happens
Real Chicago business geography, not a generic list of landmarks.
233 S Wacker and the surrounding financial corridor. Loading zones are tight and the Lower Wacker approach is faster than the surface at rush hour.
The Mart's River North bulk holds tech, showrooms and Motorola Mobility alumni. We stage on Kinzie rather than fighting the Orleans turn.
2301 S Martin Luther King Drive. Three connected buildings, 2.6 million square feet of exhibit space, and four entirely different drop-off doors.
Google, McDonald's global HQ and the restaurant row that entertains half the city's clients. Randolph closes for events more than people expect.
22nd Street and Jorie Boulevard. Ace Hardware, Blistex and the Oakbrook Center campus. About 45 minutes from the Loop off-peak.
Donald E. Stephens Convention Center and the Rosemont hotel cluster sit two miles from O'Hare, which makes them the region's default convention overflow.
Why Chicago Books Us
Six things that matter when ground transportation is a line item you have to defend.
Commercial liability coverage on every vehicle, certificate provided to your procurement team on request. This is not a rideshare policy rider.
Trip-level detail on one monthly invoice, exportable, with rider names and cost centers so expense reconciliation takes minutes.
Rates are contractual. Storms, conventions, game nights and Lollapalooza weekend do not change what your CFO sees at month end.
A person answers, around the clock. Not a chat bot, not a queue, not a driver you have never spoken to trying to find the right building.
Chauffeurs are background checked and sign NDAs. For sensitive travel we can assign a fixed chauffeur for the duration of the engagement.
Chauffeurs meet international clients at O'Hare Terminal 5, hold a name board, and know which Loop hotel entrance is the discreet one.
Common Questions
What Chicago travel managers, executive assistants and CFOs ask before opening an account.
Hourly as-directed corporate service in Chicago starts at $90 per hour for a Ford Expedition and $95 per hour for a Cadillac Escalade or Lincoln Navigator. A fourteen-passenger Mercedes-Benz Sprinter starts at $140 per hour. Point-to-point transfers from the Loop start at $95 to O'Hare or Midway and $90 to McCormick Place. Corporate accounts with meaningful monthly volume receive tiered pricing off those starting rates. Every quote is flat, before taxes and gratuity, with no fuel or surge component.
One business day in most cases. We need your billing contact, the offices and airports you travel between, a rough monthly trip volume, and the names of anyone who should have booking authority. In return you receive a rate card, a certificate of insurance, a W-9 and a short account agreement. Once procurement signs, your executive assistants can book by email or online, and every ride flows onto a single consolidated monthly invoice.
Yes, and it is a large share of what we do in Chicago. Send the itinerary and we build the day around it: staging locations between meetings, standby wait time, and multiple vehicles running in parallel when the team splits. The chauffeur holds the car rather than releasing between stops, so nobody rebooks in a lobby. For roadshows spanning the Loop, Fulton Market and the suburban corridors we assign chauffeurs who drive those routes daily.
Every chauffeur is background checked, commercially licensed and bound by a confidentiality agreement covering anything seen or heard in the vehicle. For legal, financial and healthcare clients we can assign a single named chauffeur for the length of an engagement so the same person handles every movement. The Mercedes-Benz Sprinter can be configured with a partition. Our chauffeurs do not discuss passengers, destinations or conversations with anyone, including other clients.
Yes. That is the core of a corporate account. Rides are charged to the account rather than to a rider's personal card, and every trip appears on one monthly invoice with the rider name, date, route, vehicle and cost center. Most Chicago clients set us up as a standard vendor in accounts payable and settle on net terms. Individual travelers never front cash, chase receipts, or file an expense report for ground transportation.
Yes, and meet and greet is strongly recommended for that. Most international arrivals clear customs at O'Hare Terminal 5, where clearance runs thirty to ninety minutes depending on the flight and the hour. Your chauffeur waits inside baggage claim with a name board, handles the luggage and walks the client to a vehicle at the curb rather than sending them on the long walk to the Multi-Modal rideshare facility. We track the inbound aircraft from pushback.
It runs, and it runs at the price you were quoted. Our vehicles are winter-equipped and our chauffeurs have driven the Kennedy, the Edens and the Eisenhower through February for years. Corporate account holders are dispatched with priority when supply tightens across the region. If the airport itself closes, we release the reservation with no charge. What we do not do is reprice a storm the way a surge algorithm does.
Yes. Oak Brook, Deerfield, Lake Forest, Schaumburg, Rosemont, Naperville and the entire Tri-State corridor are core territory, and many of our regular corporate runs never touch the Loop at all. Suburban pickups are quoted flat by distance rather than metered. If your company runs a shuttle pattern between a suburban headquarters and O'Hare, we will price it as a recurring route and hold the vehicles on standing reservation.
A point-to-point transfer is a single flat rate between two addresses. It is the right instrument for an airport run, a hotel to McCormick Place hop, or a straightforward client dinner drop. You pay once and the traffic is our problem.
Hourly as-directed service prices the chauffeur and vehicle by the hour, and it wins the moment your day has more than two stops, includes waiting, or has an uncertain end time. Three point-to-point transfers in a Loop afternoon almost always cost more than four hours as-directed, and the hourly car waits outside rather than making you rebook. As a rule of thumb: two stops or fewer, go flat. Three or more, go hourly.
Chicago's expressway system has personality. The Kennedy carries O'Hare traffic and reverses direction of pain between morning and evening. The Eisenhower is unforgiving westbound after 3 PM. Lower Wacker Drive is the single most valuable piece of local knowledge in the Loop, and it is not something a navigation app reaches for by default.
Add the variables. Cubs day games empty Wrigleyville into the Kennedy. Bears Sundays reroute the Museum Campus. Lollapalooza closes Columbus Drive through Grant Park for a week each summer. Marathon Sunday in October takes twenty-six miles of city streets offline. Our chauffeurs know all of these because they drive through them, and dispatch adjusts departure times before you ask.
Ask for the certificate of insurance and confirm commercial liability limits, not a personal policy with a commercial endorsement. Ask whether chauffeurs are employees or independent contractors, and whether they are background checked and drug tested. Ask how gratuity is handled and whether it is included, optional or automatic.
Then ask the questions that actually determine whether the relationship works: does dispatch answer at 3 AM, is there surge pricing under any circumstances, will you receive one invoice or twelve, and can rides be booked by an assistant on behalf of an executive without a rider account. We answer yes, no, one, and yes.
Firms that move people through Chicago consistently, whether that is a private equity shop running diligence, a law firm bringing partners in from Deerfield, or a medical device company shuttling teams to RSNA at McCormick Place in November, benefit from a standing program rather than ad hoc booking.
A standing program means fixed rate cards on your recurring routes, held vehicles on your recurring dates, priority dispatch during the weeks Chicago sells out, and named chauffeurs your executives already know. It also means one vendor relationship instead of a dozen ride receipts. Message us and describe how your people actually move, and we will price the pattern rather than the trip.
Keep Exploring
Book in Under 60 Seconds
Rate card, certificate of insurance and dispatch access. Your first ride can be tomorrow morning.
24/7 Dispatch · Flat Rates · Licensed & Insured · Chicago, Illinois