O'Hare to Milwaukee in 90 minutes
Executive transfers with zero friction—dispatch locks your route while you clear arrivals.
Dispatch uptime
24/7
Live operators
Average response
4 min
Quote to confirmation
Midwest reach
35 cities
Scouted corridors
How it works
Three steps to your ride
Share your itinerary
Flight number, hotel, or destination—we capture details in one quick interaction.
Lock the fare instantly
Stripe-powered checkout delivers confirmation, driver brief, and receipt immediately.
Track until drop-off
Dispatch monitors every mile and weather window while you focus elsewhere.
Why choose us
Built for corporate travel
Commercially insured
$5M liability coverage on every ride with compliance docs ready for procurement.
Background screened
DMV, drug, and TSA-compliant chauffeur screening through third-party auditors.
24/7 Dispatch
Live operators track GPS, weather, and client comms from our Chicago desk.
Testimonials
Trusted by travel managers
“Outbound took over our snow-day transfers with 30 minutes notice and kept every exec updated.”
“They send pricing, driver ETA, and backup options before I can refresh the airline app.”
“Our players trust the quiet cabins, and I trust the dispatcher who messages me if weather shifts.”
Client Experiences
Why Travelers Choose Outbound
“Game changer for my monthly trips to Milwaukee. No surge pricing, no stress. My driver James was early and the Suburban was immaculate. Already booked for next month!”
Sarah M.
FAQ
Common questions
How much does it cost to get from O'Hare to Milwaukee?
O'Hare to Milwaukee is 83 miles. Our all-in sedan fare starts at approximately $250 (includes 18% gratuity, ORD fees, and tolls). SUVs start around $310. No surge pricing, ever.
Do you offer 24/7 service from O'Hare?
Yes. Our dispatch team operates 24/7. Book online anytime or call (773) 641-9702 for immediate assistance.
What areas do you serve from O'Hare Airport?
We specialize in long-distance service to Milwaukee, Madison, Indianapolis, South Bend, Rockford, and throughout the Midwest.
Are gratuity and airport fees included?
Yes. Every quote includes 18% gratuity, O'Hare pickup fees, and projected tolls. The price you see is the price you pay.
What vehicles do you offer?
Executive sedans (Lincoln Continental, MKZ) for up to 3 passengers and luxury SUVs (Navigator, Escalade, Mercedes GLS) for up to 6.
How do I book a ride?
Use our instant quote online, chat with our AI concierge, or call/text dispatch at (773) 641-9702.
Ready to book?
Get an instant quote for your O'Hare pickup, or chat with our AI concierge for personalized assistance.
Or call dispatch 24/7: (773) 641-9702