Executive arrival at O'Hare with premium chauffeur service
THE ESCAPE BEGINS

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

24/7
Live operators
4 min
Quote to confirmation
35+
Cities served

How it works

Three steps to your ride

01

Share your itinerary

Flight number, hotel, or destination—we capture details in one quick interaction.

02

Lock the fare instantly

Stripe-powered checkout delivers confirmation, driver brief, and receipt immediately.

03

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.

Travel Operations Lead·Private Equity Firm

They send pricing, driver ETA, and backup options before I can refresh the airline app.

Corporate Travel Manager·Fortune 500

Our players trust the quiet cabins, and I trust the dispatcher who messages me if weather shifts.

Team Logistics·Pro Sports Club

Client Experiences

Why Travelers Choose Outbound

4.9 average rating500+ rides completed
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!
S

Sarah M.

O'Hare → Milwaukee2 weeks ago

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