By the Milwaukee to O’Hare dispatch team
Last updated: November 6, 2026
Quick answer: A corporate offsite in Chicago or Wisconsin runs on one schedule when one dispatch desk moves the whole team: airport arrivals at O’Hare and Midway grouped by landing time, a Mercedes Sprinter (13 to 15 seats with the luggage inside) for the group, sedans for executives arriving separately, hourly service that waits through the meeting and the dinner, and departures grouped the same way. Hourly Sprinter bookings carry a five-hour minimum; airport transfers are priced per trip, $199 by sedan from Milwaukee to O’Hare and by quote for Sprinters. We run inside Chicago with City of Chicago-licensed chauffeurs and across Wisconsin from our Milwaukee base, so an offsite at a Loop hotel, at McCormick Place, at the American Club in Kohler or at Grand Geneva is the same booking. Send the roster and the agenda to (414) 387-6619 and we build the movement plan.
Planning an offsite? Email the attendee list with flights and the agenda to info@milwaukeetoohare.com, or text (414) 387-6619. You get one movement plan, one invoice and one phone number for the whole event.
Start With a Movement Map, Not a Vehicle
Every offsite is the same six moves. Fill in the headcount and the time for each, and the vehicles choose themselves.
| Move | Typical headcount | What we send | Planning note |
|---|---|---|---|
| Airport arrivals, day before | 4 to 8 per wave | Sprinter per wave, or SUVs for small waves | Group by landing time within 45 minutes; last flight in the wave sets the departure |
| Hotel to venue, morning | Whole team | Sprinter(s), one trip or a loop | Leave 30 minutes before the first session; registration bottlenecks are a late-shuttle problem |
| Venue to dinner | Whole team, or split tables | Sprinter or two SUVs | Split by table, not by title, so no one waits |
| Dinner to hotel | Whole team, staggered | Hourly Sprinter waits and loops | People leave at different times; a waiting vehicle beats three dispatches |
| Executive or speaker, separate | 1 to 3 | Sedan or SUV, met inside | Separate booking, same account; name sign at baggage claim |
| Departures, last day | Waves by flight | Sprinter per wave | Leave for O’Hare 3 hours before the earliest flight in the wave; Midway 2 h 45 |
Two Airports, Two Arrival Groups
| O’Hare (ORD) | Midway (MDW) | |
|---|---|---|
| Where it is | Northwest, 17 miles from the Loop | Southwest, 10 miles from the Loop |
| Time to a Loop or River North hotel | 30 to 60 min, longer in rush hour | 25 to 45 min |
| Time to Rosemont | 10 to 15 min | 45 to 60 min |
| Time to a Milwaukee offsite | About 90 min | About 1 h 45 |
| Meeting point | Lower-level curb by door number, or inside at baggage claim with a sign | Lower-level arrivals curb, or inside |
| Rule | Prearranged livery passengers call the chauffeur after collecting bags; we text the door number at landing | Same |
Never mix the two airports in one shuttle wave; the second group waits an hour. See O’Hare airport service and Midway airport service.
Choose the Sprinter by Luggage, Not the Seat Count
| Vehicle | Seats | Bags inside | Fits |
|---|---|---|---|
| Mercedes Sprinter | 15 | 14 | A team with carry-ons and a few checked bags |
| Executive Sprinter | 13 | 12 | A leadership group that wants to work on the way; more legroom |
| Premium SUV | 6 | 5 | An arrival wave of four to six with checked bags, or the executive group |
| Sedan | 3 | 3 | A speaker, a guest, the CEO |
Fourteen people with fourteen checked bags do not fit one Sprinter; that is two vehicles or a second luggage run. Tell us bag counts with the roster. See the fleet and group transportation and Sprinters.
How the Pricing Works
| Booking type | How it is priced | Notes |
|---|---|---|
| Airport transfer, per vehicle | Per trip: $199 sedan or $234 SUV Milwaukee to O’Hare; O’Hare or Midway to a Chicago hotel by quote; Sprinter by quote | Tolls and the airport wait included; no surge on event days |
| Hourly Sprinter (as directed) | Hourly rate, five-hour minimum [confirm rate] | Covers the venue-dinner-hotel evening with one vehicle; waiting time is on the clock, not a surprise |
| Hourly sedan or SUV for an executive | Hourly rate [confirm] | Meeting day with several stops |
| Multi-day program | Day rate or itemized, one invoice | Receipts by email; monthly billing for corporate accounts |
A written quote per move before you approve the budget. See corporate and executive transfers and hourly chauffeur service.
A Sample Two-Day Offsite, 20 People
| When | Move | Vehicle |
|---|---|---|
| Day 0, 2:00 to 4:30 p.m. | Six arrivals at O’Hare in three flights; one wave | Sprinter, meets inside, leaves at 4:45 after the last bag |
| Day 0, 5:10 p.m. | Two arrivals at Midway | SUV |
| Day 0, 6:30 p.m. | CEO arrives at O’Hare | Sedan, name sign at baggage claim |
| Day 1, 8:15 a.m. | Hotel to venue, 20 people | Sprinter plus SUV |
| Day 1, 6:00 to 10:30 p.m. | Venue to dinner, dinner to hotel in two waves | Hourly Sprinter, five-hour block |
| Day 2, 12:00 to 3:00 p.m. | Departures in two waves to O’Hare, one to Midway | Sprinter, Sprinter, SUV |
Six vehicles’ worth of moves, one plan, one invoice, one number to text when a flight changes.
Venues We Run Offsites To
| Area | Venues and hotels | From O’Hare | From Milwaukee |
|---|---|---|---|
| The Loop and River North | Hotel ballrooms, the Chicago Athletic Association, Union League Club, corporate HQs | 30 to 60 min | About 90 min |
| West Loop and Fulton Market | Restaurant private rooms, Google and McDonald’s neighborhood offices | 35 to 60 min | About 90 min |
| McCormick Place and the South Loop | Trade shows and conferences | 30 to 50 min | About 90 min. See convention transportation |
| Rosemont and Schaumburg | Convention center hotels, Renaissance Schaumburg | 10 to 25 min | About 75 min |
| Milwaukee | The Pfister, Saint Kate, Fiserv Forum events, the Wisconsin Center | About 90 min | Local |
| Kohler and Lake Geneva | The American Club, Grand Geneva, Lake Lawn | Kohler 2 h 15; Lake Geneva 1 h 15 | Kohler 1 h; Lake Geneva 50 min |
The Wisconsin resort offsites are the ones Chicago operators quote as long-distance; for us they are home territory.
Hotel Blocks and Guest Instructions
| Put this in the travel brief | Why |
|---|---|
| ‘After you collect your bags, text [number]. Your chauffeur will give you the door number.’ | Removes the where-do-I-go call from every arrival |
| The shuttle departure times from the hotel, with ‘be in the lobby 10 minutes early’ | A late shuttle is a late meeting |
| Who is on the hourly evening vehicle and the last loop time | People plan their night |
| Our dispatch number, 24 hours | Flights change at 11 p.m.; someone answers |
| Executives: ‘A chauffeur with a name sign will meet you at baggage claim’ | No hunting at the curb |
We send a one-page brief template with every offsite booking. Meet-and-greet details: airport meet and greet.
Licensing, Accessibility and Loading
| Check | Our answer |
|---|---|
| Rides inside Chicago | City of Chicago-licensed chauffeurs; a Wisconsin company that is licensed for city work [confirm wording] |
| Insurance for a corporate account | Commercial liability certificate on request [confirm figure] |
| Accessible transport | SUV with device stowed, or an accessible vehicle arranged with notice; tell us the device |
| Loading at downtown hotels | Sprinters load at the curb or the porte-cochère; tall vans do not fit some garages, so we never plan a garage stop |
| Navy Pier, McCormick Place | No coach staging; we drop and return when the group is ready |
See our chauffeurs and reviews.
Seven Checks Before You Approve the Budget
| # | Check |
|---|---|
| 1 | Roster with flight numbers, both airports, and bag counts |
| 2 | Arrival waves grouped within 45 minutes; no wave mixes O’Hare and Midway |
| 3 | Sprinter count by luggage, not by seats |
| 4 | Hourly blocks for the evening, five-hour minimum, with the last loop time |
| 5 | Executives and speakers on separate sedans, met inside |
| 6 | Departure waves leave 3 hours before the earliest flight (O’Hare) or 2 h 45 (Midway) |
| 7 | One invoice, one dispatch number, one travel brief sent to attendees |
What Riders Say
“Way beyond the service I expected.” — Mark D., Google review
“Murad is a pro.” — J. A., Google review (pickup at ORD in busy conditions)
“On time, courteous, professional.” — Gail K., Google review
Quick Facts
| Fact | Detail |
|---|---|
| Service | Corporate offsite transportation in Chicago and Wisconsin: airport waves, venue shuttles, evening hourly, executive sedans |
| Sprinter | 15 seats, 14 bags; Executive Sprinter 13 seats |
| Hourly minimum | Five hours for Sprinters |
| Airport transfer | $199 sedan, $234 SUV Milwaukee to O’Hare; Chicago-side transfers by quote |
| Billing | One invoice; monthly billing for corporate accounts; receipts by email |
| Inside Chicago | City of Chicago-licensed chauffeurs |
| Operated by | Pharaoh’s Transportation, 5151 S Howell Ave, Suite D1 & D2, Milwaukee, WI 53207 |
| Phone | (414) 387-6619 |
| Hours | 24 hours a day |
Frequently Asked Questions
Can one shuttle collect employees at both O’Hare and Midway?
Not in one wave; the airports are 40 minutes apart and the second group would wait an hour. We send a vehicle per airport and group arrivals by landing time.
How many people fit in a Sprinter?
15 with carry-ons; the Executive Sprinter seats 13. See the fleet.
Is there a five-hour minimum on Sprinters?
Yes, for hourly bookings. Airport transfers are priced per trip with no minimum.
Can the chauffeur wait during our meeting and dinner?
Yes, on an hourly booking. See hourly chauffeur service.
What if a guest’s flight lands after the shuttle leaves?
We track every flight on the roster. A late arrival gets a sedan or rides the next wave; dispatch tells the organizer, not the guest.
Are hotel pickups included?
Hotel-to-venue and venue-to-hotel moves are booked as their own legs or inside an hourly block; nothing is assumed. The movement plan lists every leg.
Do you run offsites inside Chicago, or only to and from Wisconsin?
Both. See Chicago and the suburbs and Wisconsin.
Can executives arrive separately from the team?
Yes. See corporate and executive transfers.
Can we book accessible group transportation?
Yes. Tell us the device; we stow it in an SUV or arrange an accessible vehicle with notice.
How do you price a multi-day program?
Per leg or a day rate, in one written quote before you approve, and one invoice after. Corporate accounts get monthly billing.
How far ahead should we book an offsite?
Two to three weeks for a 20-person program; more for convention weeks when Chicago hotels and vehicles fill. Small executive moves can be same-day.
How do I start?
Send the roster, flights and agenda to info@milwaukeetoohare.com or text (414) 387-6619, or book online.
Make the offsite run on the meeting schedule. Text (414) 387-6619 or email the roster to info@milwaukeetoohare.com. One plan, one invoice, one number.
Related Services and Guides
- corporate and executive transfers
- group transportation and Sprinters
- convention transportation
- hourly chauffeur service
- O’Hare airport service
- Midway airport service
- O’Hare to downtown Chicago
- Milwaukee to Chicago
- Chicago hotels to O’Hare and Midway
- Milwaukee to O’Hare business travel guide
- Airport meet and greet
- Airport car service
Milwaukee to O’Hare is a division of Pharaoh’s Transportation, 5151 S Howell Ave, Suite D1 & D2, Milwaukee, WI 53207, two minutes from Milwaukee Mitchell Airport. We serve Milwaukee, all of Wisconsin, Chicago, the Chicago suburbs and Northwest Indiana, 24 hours a day. Find us on Google.
About the Dispatch Team
This guide was written by the Milwaukee to O’Hare dispatch team, part of Pharaoh’s Transportation. We move corporate teams between the Chicago airports, downtown, Rosemont and Wisconsin every week, with background-checked, licensed, insured chauffeurs, and we have for more than ten years. Call or text (414) 387-6619, open 24 hours.
