AD SERIES AUTOMOTIVE TOUR

Chicago 2022

Cruise through the Midwest on this Chicago based loop. Short leisurely drives will leave enough time to enjoy Chicago and the state of Wisconsin.

5 days / 4 Nights from $2,475

October 19 – 23, 2022

Limited to 30 vehicles

Email us at info@adventuredrives.com or call us at +1.866.803.7483

INCLUDED WITH EVERY ADVENTURE DRIVES TRIP:

  • One-of-a-kind Itinerary and Route Designed for You
  • Curated Route from Destination to Destination
  • Full Luggage Support
  • Airport Meet and Greet with Private Transfers
  • 3 Full Meals a Day
  • Activities, Entrance Fees and Taxes
  • Adventure Drives Gear
  • 24/7 Adventure Drives On-Call Support
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Our trip will begin and end in Chicago, Illinois. We will be exploring some of the scenic backroads of Wisconsin while saving enough time for some unique activities. 

Itinerary at a glance


  • Day 1 – Arrive Chicago, IL
  • Day 2 – Madison, WI
  • Day 3 – Green Bay / Milwaukee, WI 
  • Day 4 – Chicago, IL 
  • Day 5 – Depart Chicago, IL
  • DAY 1 – ARRIVE CHICAGO, IL

We will begin our tour in Chicago, Illinois. On your first day, there will be a quick check in and a welcome dinner. We will be starting driving early the following morning but that won’t mean you can’t explore downtown Chicago.

Luxury Accommodation in Chicago
 Meals: Dinner

  • DAY 2 – MADISON, WI

On our first day of driving, we will be exploring some of the more rural roads of Wisconsin ending in Madison. 

Luxury Accommodation in Madison
 Meals: Breakfast, Lunch, Dinner

  • DAY 3 – GREEN BAY / MILWAUKEE, WI

On day 3, we will continue to explore the best backroads and lake shores drives that Wisconsin has to offer. 

Luxury Accommodations in Milwaukee
 Meals: Breakfast, Lunch, Dinner

  • DAY 4 – CHICAGO, IL

Our final day of driving will have us back to Chicago with enough time to explore the places you missed on the first day. We will end our trip in style with a closing dinner in the heart of Chicago. 

Luxury Accommodation in Chicago
 Meals: Breakfast, Lunch, Dinner

  • DAY 5 – DEPART CHICAGO, IL

Day 5 will be a departure day. Enjoy a leisurely breakfast and get ready to head back home with a lifetime of memories. 

N/A
 Meals: Breakfast

*Details subject to change

Our trip will be operating from October 19 – 23, 2022.

  • Full Trip Two Persons, One Vehicle – $4,950
    • Does not include Vehicle. We can help you rent a vehicle. 
    • Does not includes flights or transport of your vehicle to the start or from the end point. We can help you arrange transport and flights.
    • Includes all Meals, Hotels (please specify if two beds or one is requested, we will do our best to accommodate your preference), and activities.
    • Does not include fuel, tolls or incidental expenses. 
    • Addition of an additional vehicle can be accommodated for a small additional charge. 
  • Full Trip One Person, One Vehicle – $4,250
    • Same as above but you get your own room. 
    • Does not include Vehicle. We can help you rent a vehicle. 
    • Does not includes flights or transport of your vehicle to the start or from the end point. We can help you arrange transport and flights.
    • Includes all Meals, Hotels, and activities.
    • Does not include fuel, tolls or incidental expenses. 
  • Full Trip Half Spot, One Vehicle – $2,475
    • We pair you up with another participant. You will share a room on the trip. 
    • Does not include Vehicle. We can help you rent a vehicle. We will help you work with the person you are paired with to decide on vehicle choice.
    • Each of you can take a vehicle for a small additional fee. 
    • Does not includes flights or transport of your vehicle to the start or from the end point. We can help you arrange transport and flights.
    • Includes all Meals, Hotels, and activities.
    • Does not include fuel, tolls or incidental expenses. 

This journey may contain some active elements.

All Pricing is in USD and subject to change.
Minimum age is 10 years.
First group event: Welcome dinner October 19, 2022. Time TBD
Last group event: Farewell breakfast October 23, 2022. Time TBD. 

AT A GLANCE:

Your Journey:
AD09 Canada
  • Approximate Mileage: 650

  • Average High / Low Temps: 55/80 (F)

  • Arrival Airport: O’Hare International (ORD)

  • Departure Airport: O’Hare International (ORD)

  • Currency: U.S. Dollar (USD)

  • Time Zone(s): Central (GMT -6)

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