Written by the Milwaukee to O’Hare dispatch team, a division of Pharaoh’s Transportation, 5151 S Howell Ave, Milwaukee. Rated 4.9 from 302 Google reviews; every chauffeur is background-checked, licensed and insured.
Quick answer: A Milwaukee day trip from Chicagoland works best with one chauffeured vehicle for the whole day: pickup at your home or hotel in Chicago or the suburbs, about 1.5 hours to downtown Milwaukee (under an hour from Lake County), the chauffeur on hand between stops, and the ride home the same night. A premium SUV seats up to 6; a Sprinter seats 13 to 15 for birthdays, family reunions and company outings. Book it by the hour or as a round trip with a set return time through milwaukeetoohare.com, a division of Pharaoh’s Transportation. Call (414) 322-3751, 24/7.
Day trip to Milwaukee?
Tell us your pickup, headcount and stops. We confirm the vehicle and the rate in writing.
Key takeaways
- Downtown Chicago to downtown Milwaukee is about 90 miles: 1.5 to 2 hours by car.
- From the North Shore and Lake County it is about 45 minutes to 1.25 hours.
- Leave by 8:30 or 9 AM for a full day; home between 9 and 11 PM.
- Hourly booking keeps the vehicle with you between stops; a round trip is a drop-off and a set pickup.
- SUV for up to 6, Sprinter for 13 to 15, two vehicles for bigger groups.
In this guide
- How a Milwaukee day trip works
- Pickup times from Chicagoland
- Four day plans that work
- Evenings in Milwaukee
- Vehicles for the day
- Milwaukee in every season
- Book through Pharaoh’s or our divisions
- How to book
- Frequently asked questions
How a Milwaukee day trip works
One vehicle, your schedule, both ways.
Two ways to book
| Option | How it works | Best for |
|---|---|---|
| Hourly, as directed | The chauffeur stays with you all day and drives between every stop. | Several stops, families, groups, winter days |
| Round trip with a set return | Drop-off in Milwaukee in the morning, pickup at a time and place you choose. | One main stop: a museum, a game, a dinner |
Not sure? Tell dispatch your stops and we quote both in writing [CONFIRM rates].
Why not drive or take the train
The train gets you downtown, but not to the Harley-Davidson Museum, the lakefront and a restaurant in Bay View in one afternoon, with kids, shopping bags or a group of 12. Driving yourself means 3 hours at the wheel, Milwaukee parking and someone staying sober for the drive home. Our train, bus and car comparison has the numbers.
Both directions
Wisconsin families do the same trip the other way for a day in Chicago. Both directions are booked the same way through our Chicago routes.
Pickup times from Chicagoland
For a 10:00 AM start in downtown Milwaukee. Dispatch confirms yours the day before.
Chicago and the suburbs
| Pickup area | Drive to downtown Milwaukee | Pickup time | Home by about (leave Milwaukee 8 PM) |
|---|---|---|---|
| The Loop, River North, Gold Coast, West Loop | About 1.5 to 2 hours | About 8:15 AM | 9:45 PM |
| Lincoln Park, Lakeview, the North Side | About 1.5 hours | About 8:30 AM | 9:30 PM |
| Evanston, Wilmette, Winnetka, Glencoe | About 1.25 hours | About 8:45 AM | 9:15 PM |
| Highland Park, Lake Forest, Deerfield, Northbrook | About 1 to 1.25 hours | About 8:50 AM | 9:10 PM |
| Gurnee, Libertyville, Vernon Hills, Waukegan | About 45 minutes to 1 hour | About 9:10 AM | 8:55 PM |
| Arlington Heights, Palatine, Schaumburg | About 1.25 to 1.5 hours | About 8:30 AM | 9:30 PM |
| Naperville, Oak Brook, the western suburbs | About 2 hours | About 8:00 AM | 10:00 PM |
| Crystal Lake, McHenry, Barrington | About 1.25 hours | About 8:45 AM | 9:15 PM |
| Northwest Indiana | About 2 to 2.5 hours | About 7:30 AM | 10:30 PM |
Hotel guests and visitors
Staying at a Chicago hotel? We pick up at the front entrance. Flying in to O’Hare or Midway and spending a day in Milwaukee before you fly home? We can start at the airport and end at your hotel.
Planning your Milwaukee day?
Send your pickup address, the headcount, the stops you have in mind and your latest return time. We send the plan and the rate in writing.
Four day plans that work
Starting points; move stops around to fit your group. Check each place’s hours before you go [CONFIRM].
The lakefront and museums
| Time | Stop |
|---|---|
| 10:00 AM | Milwaukee Art Museum on the lakefront: the Calatrava pavilion and its moving “wings” |
| 12:30 PM | Lunch downtown or in the Third Ward |
| 2:00 PM | Discovery World, next door on the lake (good with kids) |
| 4:00 PM | Veterans Park and the lakefront path, or Bradford Beach in summer |
| 6:00 PM | Dinner on the East Side or downtown, then the ride home |
The Third Ward and food
| Time | Stop |
|---|---|
| 10:00 AM | Milwaukee Public Market: coffee and a walk through the Historic Third Ward |
| 11:30 AM | Shops and galleries in the Third Ward; the Riverwalk |
| 1:00 PM | Lunch; a brewery or distillery tour in the afternoon |
| 4:00 PM | Brady Street or Bay View |
| 6:30 PM | Dinner, then home |
Motorcycles and breweries
| Time | Stop |
|---|---|
| 10:00 AM | Harley-Davidson Museum in the Menomonee Valley |
| 12:30 PM | Lunch at the museum or nearby |
| 2:00 PM | A brewery tour (book ahead) [CONFIRM] |
| 4:30 PM | Downtown and the Riverwalk |
| 6:30 PM | Dinner, then home |
With a chauffeur, nobody has to skip the tasting.
Family day
| Time | Stop |
|---|---|
| 10:00 AM | Milwaukee County Zoo (west side) |
| 1:00 PM | Lunch |
| 2:30 PM | Discovery World or the lakefront |
| 5:00 PM | Early dinner and an earlier drive home |
Bringing car seats? Tell dispatch when you book [CONFIRM car-seat policy].
Evenings in Milwaukee
Many Chicagoland visitors come up for the night, not the day.
Games and concerts
Bucks and Marquette at Fiserv Forum, Brewers at American Family Field, and shows downtown. See Chicago to Fiserv Forum for a Bucks game and the game-day guide.
Dinner and back
A dinner reservation in the Third Ward or downtown, a walk on the Riverwalk, and home by midnight. Pickup about 4:30 PM from the city, the chauffeur waits, and the ride home starts when you are ready.
Staying over
Want a night in Milwaukee? We run two legs: up on day one, home on day two.
Vehicles for the day
The vehicle stays with the group, so it is part of the day.
Premium SUV, up to 6
Couples, families and friends. Leather seats, room for shopping bags and a stroller. See SUV service.
Sprinters for 13 to 15
Birthdays, bachelorette days, family reunions and company outings: everyone together, room to stand. See the Mercedes Sprinter and the Executive Sprinter.
Bigger groups
Two or more vehicles on one booking, arriving together. See group transportation.
Milwaukee in every season
The day changes with the weather; the ride does not.
Summer
The lakefront, beaches, festivals at Henry Maier Festival Park and Brewers games. Weekends fill early.
Fall
Museums, the Third Ward and Bucks season. Comfortable days and the easiest traffic.
Winter
Indoor plans: museums, the Public Market, a brewery tour and dinner. A warm vehicle waits outside every stop, and dispatch watches the I-94 forecast.
Spring
Brewers home openers and the first lakefront walks. Book Saturdays early.
Book through Pharaoh’s or our divisions
milwaukeetoohare.com is a division of Pharaoh’s Transportation. All three sites use one office, one 24/7 dispatch team and the same fleet.
Where to book
Here on milwaukeetoohare.com, on pharaohstransportation.com, or on our statewide division wisconsinlimoservice.com. Call (414) 322-3751 any hour.
The same standards everywhere
Professional chauffeurs who are background-checked, licensed and insured; a written rate before the ride; and a company rated 4.9 from 302 Google reviews. Pharaoh’s office: 5151 S Howell Ave, Suite D1 & D2, Milwaukee, WI 53207.
How to book
About two minutes online or by phone.
Step 1: Pick the date
Weekday or weekend, and any event you are going to.
Step 2: Send the pickup
Home, office, hotel or airport in Chicagoland.
Step 3: List the stops
Or tell us the plan and we suggest the order.
Step 4: Set the return
Latest time you want to be home.
Step 5: Get it in writing
Vehicle, times and rate on one confirmation: (414) 322-3751 or book online.
Related routes and services
- Chicago routes
- Chicago to Milwaukee for a business day
- Milwaukee to Chicago car service
- Hourly chauffeur service
- Mercedes Sprinter for 15
Quick Facts
| Fact | Detail |
|---|---|
| Trip | Chicagoland to Milwaukee and back the same day |
| Drive | About 1.5 to 2 hours from downtown Chicago |
| Booking | Hourly or round trip, per vehicle |
| Vehicles | SUV (6), Executive Sprinter (13), Mercedes Sprinter (15) |
| Operator | Pharaoh’s Transportation (milwaukeetoohare.com is a division) |
| Office | 5151 S Howell Ave, Suite D1 & D2, Milwaukee, WI 53207 |
| Phone | (414) 322-3751, 24/7 |
| Rating | 4.9 from 302 Google reviews |
Frequently asked questions
Planning
How long is the drive from Chicago to Milwaukee?
About 90 miles, 1.5 to 2 hours from downtown Chicago; under an hour from Lake County.
What time should we leave Chicago?
About 8:30 AM from the city for a 10 AM start in Milwaukee.
Can we do Milwaukee in one day?
Yes; three or four stops plus dinner fit comfortably.
Can we start at O’Hare or Midway?
Yes; we can pick up at the airport and end at your hotel.
On the day
Does the chauffeur stay with us?
Yes, on an hourly booking; on a round trip we drop off and return at a set time.
Can we change the plan during the day?
On an hourly booking, yes; tell the chauffeur.
Can we have drinks on a brewery tour?
Yes; nobody in your group has to drive.
What if we want to stay later?
Call dispatch; extra time is billed as agreed when you book [CONFIRM].
Booking and groups
How is the day priced?
By the hour or as a round trip per vehicle, confirmed in writing.
What vehicle for 12 people?
A Sprinter: the Executive Sprinter seats 13 and the Mercedes Sprinter 15.
Do you pick up in the western suburbs or Northwest Indiana?
Yes; see the pickup table for times.
Are chauffeurs licensed and insured?
Yes, every chauffeur is background-checked, licensed and insured.
Ready for Milwaukee?
Book online or call dispatch any hour. Rate confirmed in writing before you ride.
About the Milwaukee to O’Hare dispatch team
milwaukeetoohare.com is the Chicago-corridor division of Pharaoh’s Transportation. The same dispatch team plans every ride between Wisconsin and Chicagoland, both ways, every day of the year, from the office at 5151 S Howell Ave, Suite D1 & D2, Milwaukee. Chauffeurs are background-checked, licensed and insured and drive I-94 between the two cities daily. Dispatch answers 24 hours a day at (414) 322-3751.
