Wine tours from Chicago, with a chauffeur for the whole day.
Wine tours from Chicago with a chauffeur who drives all day, so everyone in your group can taste. Pick the wineries and breweries, or let us help plan the route.
- Flat-rate airport pricingQuoted before you ride
- Flight trackingOn every airport pickup
- 2025 and 2026 vehiclesDetailed before each trip
- Background-checked chauffeursLicensed and professional
- Live dispatch 24/7Holidays included
Book your tasting day online.
Pick the date, group size, and vehicle online. Your chauffeur will be at your door in the morning.
What we handle
- Pickup at your home or hotel in Chicago or the suburbs
- A route to the wineries you pick, or one we suggest
- A chauffeur who waits at every winery and brewery
- Room for the bottles you buy
- Start times planned around Michigan's Eastern time
- Your car and chauffeur are confirmed before the day
- Chauffeur arrives early
- Background-checked chauffeurs
Planning for a big group? See our group transportation options.
Reserve your ride online
Booking takes about a minute. You get a confirmation by email, and your car and chauffeur are set before the day you ride.
Book your ride- Secure online booking
- Open 24/7
- No phone call needed
Wine tours from Chicago where nobody has to drive.
Your group gets a professional driver and a comfortable vehicle for the day. Everyone tastes, and nobody drives.
Tell us where you want to go, or what you like, and we plan the stops and the timing.
A wine day is popular with birthday groups, bachelorette parties, work teams, and couples.
Why book a wine tour
- A custom route you choose
- The whole group rides together
- You set the pace
Wine tour destinations from Chicago.
The four trips groups ask about most.
| Destination | Where | Good to know |
|---|---|---|
| Lake Michigan Shore Wine Trail | Southwest Michigan | Wineries include Fenn Valley, Lemon Creek, 12 Corners, and Hickory Creek. About 90 minutes to 2 hours from the Loop. Michigan is on Eastern time, one hour ahead. |
| Lake Geneva | Wisconsin, about 75 miles northwest of Chicago | A lake resort town, good for a full day out. |
| Lynfred Winery | Roselle, in the suburbs | Founded in 1979. A good pick for a shorter trip. |
| Galena | Northwest Illinois, in the Upper Mississippi River Valley wine region | Wineries on Main Street in a historic town. The longest drive of the four, so plan a long day or an overnight. |
Some tasting rooms ask groups to reserve. Check with each winery, then send us the times.
What every wine tour includes.
A full day out, and we do all the driving.
A planned route
- Stops in a sensible order
- Drive times built in
- Lunch stop if you like
A comfortable vehicle
- Sprinter, SUV, or limo bus
- Room for purchases
- Climate set for the group
Clear pricing
- Hourly rate set first
- Minimum confirmed at booking
- Easy to split
Best vehicles for a wine tour.
Pick by group size. Groups of 11 or more usually take the Sprinter or the limo bus.
Mercedes-Benz Sprinter
From $160 per hour
Cadillac Escalade
From $100 per hour
Limo Bus
From $325 per hour
Chevrolet Suburban
From $135 per hourNot sure which fits? Compare all ten vehicles or see hourly rates.
Wine tour pickups across Chicago and the suburbs.
We pick up anywhere in Chicagoland, at one home or several, and bring everyone back to their own door. Downtown groups head south on the Dan Ryan toward Michigan. North Shore groups head north toward Lake Geneva.
Live farther out? Email us. We likely cover your town and confirm the price before you book. See all service areas.
How a chauffeured wine tour works.
Plan once, then enjoy the day.
Pick the stops
- Wineries and breweries you like
- Or ask us for ideas
- Group size and start time
Taste and relax
- Chauffeur drives every leg
- Waits at each stop
- Adjust the plan as you go
A safe ride back
- Dropped at your door
- Purchases loaded for you
- Bottles carried in for you
Weekends in warm months book first. Reserve online early if you need a Sprinter or limo bus.
Related services and areas.
How do wine tours with a chauffeur work?
Where can we go for a wine tour from Chicago?
How long is the drive to the Michigan wineries?
Do you include breweries?
How big a group can you take?
How are wine tours priced?
Wine tours from Chicago to Southwest Michigan, Lake Geneva, Galena, and the suburbs, with a chauffeur for the whole day and vehicles for groups of any size.
Plan your day of tasting.
Send your group size, date, and the wineries you want to visit. We send back a route, the timing, and a price.
Live dispatch, 24/7. Your price is confirmed before you ride.