City-to-City Transfer Service
Travel between Chicago and major Midwest cities in comfort and style. Our long-distance transfer service provides a productive, relaxing alternative to flights and trains for distances up to 500 miles.
How much does city-to-city car service cost from Chicago?
Chicago city-to-city transfer rates: Milwaukee $195 (1.5 hrs), Indianapolis $325 (3 hrs), Detroit $450 (4.5 hrs), St. Louis $475 (5 hrs). All prices are flat-rate with no hidden fees. Includes door-to-door service, complimentary WiFi, bottled water, and flight tracking for airport pickups. Group discounts available.
Popular Routes
Flat-rate transfers from Chicago to major Midwest destinations.
* Prices shown are for executive sedan. SUV and Sprinter rates available upon request.
Why Choose Car Service
For distances under 500 miles, executive car service often beats air travel in cost, convenience, and productivity.
Door-to-Door Convenience
Pickup at your office, home, or hotel and drop directly at your destination. No parking, no security lines, no connections.
Productive Travel Time
Work, rest, or prepare for meetings while traveling. WiFi, charging, and privacy let you maximize every minute.
Flexible Scheduling
Depart when you want, not when the flight leaves. Early morning, late night, or last-minute - we accommodate your schedule.
Cost-Effective for Groups
For 2+ travelers, car service often costs less than flights plus ground transportation at both ends. No baggage fees or parking costs.
Vehicle Options
Executive Sedan
Solo executive or pair
Premium SUV
Small groups with luggage
Mercedes Sprinter
Teams and delegations
Car Service vs. Air Travel
For trips under 350 miles, car service is often faster door-to-door.
Executive Car Service
- ✓ Door-to-door pickup and dropoff
- ✓ No security lines or wait times
- ✓ Work privately during transit
- ✓ Unlimited luggage
- ✓ Depart on your schedule
Air Travel
- ✗ Requires ground transport at both ends
- ✗ TSA screening and boarding time
- ✗ Limited privacy and workspace
- ✗ Baggage fees and restrictions
- ✗ Fixed departure times
Transfer FAQs
How are city-to-city transfers priced?
Intercity transfers are quoted as flat rates based on distance and vehicle type. Prices include all tolls and taxes. Gratuity is additional. We provide exact quotes before booking with no hidden fees.
Can we make stops along the way?
Yes, reasonable stops for meals, restrooms, or brief meetings can be accommodated. Extended stops may result in additional charges. Please discuss your itinerary when booking.
What happens if we experience traffic delays?
Our flat-rate pricing means traffic delays don't affect your cost. Our chauffeurs use real-time navigation to minimize delays, and we build buffer time into all schedules.
Is round-trip service available?
Yes. We offer same-day round trips, multi-day round trips, and one-way transfers. Round trips typically qualify for discounted rates. We can accommodate return trips on different days.
What if my return schedule changes?
We understand business schedules are fluid. Return trips can be modified with reasonable notice. Same-day changes are accommodated when possible, subject to vehicle availability.
Do you serve destinations not listed?
Absolutely. We provide service throughout the Midwest and can arrange transportation to any destination. Contact us for a custom quote for unlisted destinations.
Book Your Intercity Transfer
Travel in comfort between Chicago and the Midwest.