Instant Quote & Best Rates
Get your all-inclusive quote in seconds — fast, transparent pricing with no hidden fees.
Hourly Chauffeur Service
Hire a professional chauffeur by the hour or for the full day — perfect for meetings, errands, or special events.
Travel Solo or with a Group
From executive sedans to spacious SUVs, we offer flexible ride options tailored for individuals, families, and business groups.
0ur Fleets
Routes from Chicago to Milwaukee
Travel in comfort from Chicago to Milwaukee with our premium transfer service at affordable, all-inclusive rates. Enjoy a seamless, stress-free journey tailored for both business and leisure.
Homewood Suites by Hilton
Courtyard Chicago Downtown
(92.5 miles) – Time, 2 hr 7 min
SEDAN
$140/hour
Mid Size SUV
$156/hour
Full Size SUV
$181/hour
Wisconsin Centre
Chicago Downtown
(119 miles) – Time, 2 hr 28 min
SEDAN
$140/hour
Mid Size SUV
$156/hour
Full Size SUV
$181/hour
Milwaukee's Historic Third Ward
Chicago Downtown
(93 miles) – Time, 2 hrs
SEDAN
$140/hour
Mid Size SUV
$156/hour
Full Size SUV
$181/hour
O'Hare Int Airport (ORD)
Milwaukee
(79.3 miles) – Time, 1 hr 15 min
SEDAN
$140/hour
Mid Size SUV
$156/hour
Full Size SUV
$181/hour
Chicago Midway Int Airport (MDW)
Milwaukee
(104 miles) – Time, 1 hr 52 min
SEDAN
$140/hour
Mid Size SUV
$156/hour
Full Size SUV
$181/hour
Milwaukee Mitchell Int Airport (MKE)
Chicago
(84.7 miles) – Time,
1 hr 26 min
SEDAN
$140/hour
Mid Size SUV
$156/hour
Full Size SUV
$181/hour
Car seat $30
Meet and Greet $40
Ride in Comfort from Chicago to Milwaukee
Skip the stress of driving or unreliable rideshares. Our professional chauffeurs provide reliable, luxury black car service between Chicago and Milwaukee.
The Connection Between Chicago and Milwaukee
Chicago and Milwaukee are more than just neighbouring cities—they are two thriving hubs of business, culture, and entertainment connected by a vibrant corridor along Interstate 94. With just under 90 miles between them, travelling from Chicago to Milwaukee has never been easier, especially with Chi-Town Black Cars at your service.
Whether you’re visiting Milwaukee Mitchell International Airport (MKE), attending a conference downtown, or planning a special event, our city-to-city car service ensures you arrive on time and in style. Skip the hassle of rental cars, unpredictable rideshares, or crowded trains. Instead, experience the personal touch of a private chauffeur who knows the route, understands your needs, and delivers first-class service every mile of the way.
Premium City-to-City Transfers
At Chi-Town Black Cars, we specialise in private transfers between Chicago and Milwaukee for business travellers, leisure guests, and special occasions.Our experienced chauffeurs ensure a smooth journey along the scenic Interstate 94 corridor, with an average travel time of 1.5 to 2 hours, depending on traffic. Covering approximately 92 miles, we offer an unmatched blend of luxury, efficiency, and personal service.
Airport Transfers
Whether you’re departing from or arriving at a major airport, we provide luxury black car service connecting:
- O’Hare International Airport (ORD) to Milwaukee:
83 miles | 1 hour 30 minutes travel time. - Midway International Airport (MDW) to Milwaukee: 93 miles | 1 hour 40 minutes travel time.
- Milwaukee Mitchell International Airport (MKE) to Downtown Chicago: 85 miles | 1 hour 35 minutes travel time.
Executive Transfers
For executives and business professionals, punctuality and discretion are essential. Our executive car service from Chicago to Milwaukee offers:
- Quiet, private cabins ideal for phone calls or working on the go.
- Professional chauffeurs with real-time traffic monitoring.
- Direct pickups from offices, hotels, and convention centres across Chicago and Milwaukee.
Wedding Transfers
Planning a wedding? Trust Chi-Town Black Cars to handle transportation with elegance and precision.
We offer:
- Transfers between Chicago and beautiful Milwaukee venues like The Atrium and The Ivy House.
- Group transportation for wedding parties.
- Stylish arrivals for the bride and groom in luxury SUVs and sedans.
Sporting Events Transfers
Sports fans, we’ve got you covered! Our black car service to sporting events ensures you never miss a minute of the action. Travel between cities in comfort, whether you’re:
- Catching a Milwaukee Brewers baseball game at American Family Field.
- Heading to see the Milwaukee Bucks at Fiserv Forum.
- Attending a special event like the Milwaukee Mile racing event.
Attractions Along the Route
One of the benefits of booking a private car service from Chicago to Milwaukee is the ability to enjoy the journey just as much as the destination.Along the scenic drive up Interstate 94, there are several attractions worth noting:
Pleasant Prairie Premium Outlets
Pleasant Prairie Premium Outlets
Bristol Renaissance Faire
Bristol Renaissance Faire
Lakefront Views
Lakefront Views
Historic Downtown Racine
Historic Downtown Racine
Book Your Luxury Ride from Chicago to Milwaukee Today!
Travel between Chicago and Milwaukee in the ultimate style and comfort with Chi-Town Black Cars.
Whether you’re heading to the airport, an important meeting, a wedding, or a big game, our professional chauffeurs are here to deliver a first-class city-to-city transfer experience.
- Reliable service 24/7
- Luxury fleet of sedans, SUVs, and black cars
- Professional, discreet chauffeurs
- Easy booking and transparent pricing
Top Routes
Midway International Airport (MDW)
Milwaukee Mitchell Intl Airport (MKE)
O'Hare International Airport (ORD)
Downtown Chicago
Chicago suburbs
FAQS
The distance from Chicago to Milwaukee is approximately 92 miles via I-94 W.
Travel time typically ranges from 1.5 to 2 hours, depending on traffic conditions and pick-up/drop-off points.
Yes, Chi-Town Black Cars specialises in luxury airport transfers between Chicago’s airports and Milwaukee.
We provide black car service from O’Hare (ORD) and Midway (MDW) directly to Milwaukee hotels, residences, and event venues.
Absolutely! We offer executive black car service, perfect for corporate clients travelling between Chicago and Milwaukee.
Enjoy a private, quiet ride in a luxury sedan or SUV, complete with professional chauffeurs focused on discretion and punctuality.
Rates vary based on vehicle type and specific pickup/drop-off locations.
For an accurate quote, please contact us directly or call
We offer transparent pricing with no hidden fees for all city-to-city transfers.
Yes! Chi-Town Black Cars provides luxury wedding transportation for both small and large groups.
We can transport wedding parties, guests, and even newlyweds between Chicago and Milwaukee with elegance and reliability.
Of course! Whether you’d like to stop at the Pleasant Prairie Premium Outlets, a favourite restaurant, or scenic locations along Lake Michigan, we offer customizable itineraries for a more personalised travel experience.
Our fleet includes luxury sedans, black SUVs, and executive sprinter vans, ensuring a premium ride tailored to your needs — whether you’re travelling solo, as a couple, or with a larger group.
