All Trips · Americas
Chicago and Wisconsin’s Great Lakes
Iconic Cities, Lake Michigan, Lighthouses and Scenic Coastal Roads
Duration
8 Days / 7 Nights
Starts
Chicago
Ends
Chicago
Car
Chevrolet Spark or Similar
Hotels
4 Cities
Stay as many nights as you wish
Your package price updates instantly
Flights, hotels & car in one booking
Secure online payment
Overview
Discover Chicago and the landscapes of Wisconsin on a flexible seven-night self-drive vacation from and back to Chicago.
Begin with two nights in Chicago, giving you time to experience its celebrated architecture, lakefront, museums and distinctive neighbourhoods without needing a rental car.
Collect your car on Day 3 and follow Lake Michigan north to Milwaukee. Explore the city’s waterfront, RiverWalk, brewing traditions and historic neighbourhoods before continuing to Door County.
Two nights in Door County provide time for the peninsula’s scenic coastal roads, picturesque waterfront communities, lighthouses and Peninsula State Park.
Travel inland to Madison, Wisconsin’s attractive state capital, beautifully positioned between Lakes Mendota and Monona. Complete your loop with a final night in Chicago before returning to the airport.
The suggested package includes seven nights, but your vacation is fully flexible. Add or remove nights, choose your preferred hotels and select the rental-car category that best suits your needs.
You decide how long you stay!
Perfect for
Self-Drive Trips
Couples
Friends Travelling Together
Architecture Lovers
Road Trippers
Coastal Explorers
Food & Beer Fans
Flexible Travellers
Your Itinerary Overview
8 Days · 7 Nights
WELCOME TO CHICAGO
CHICAGO TO MILWAUKEE
MILWAUKEE TO DOOR COUNTY
DOOR COUNTY TO MADISON
Your route. Your pace.
Add or remove nights at every destination. Your itinerary and package price update instantly.
1
Start
WELCOME TO CHICAGO
Swissotel - Chicago2 nights
2
Day 2
DISCOVER CHICAGO
Swissotel - Chicago2 nights
3
Day 3-4
CHICAGO TO MILWAUKEE
The Knickerbocker on the Lake1 night
4
Day 4-6
MILWAUKEE TO DOOR COUNTY
Newport Resort2 nights
5
Day 5-6
DISCOVER DOOR COUNTY
Newport Resort2 nights
6
Day 6-7
DOOR COUNTY TO MADISON
Swissotel - Chicago1 night
7
Day 7-8
MADISON TO CHICAGO
Swissotel - Chicago1 night
8
Day 8
DEPARTURE FROM CHICAGO
Choose your rental car
Prices shown for a 8-day rental.More rental cars available — drag sideways or use the arrows to explore
Type
Why You'll Love This Trip
A ready-made loop — no backtracking
Fully flexible — add or remove nights as you like
No rental car needed for your first two days in Chicago
Four genuinely different destinations in one trip
Scenic coastal roads along Lake Michigan and Door County
Wide choice of hotels at every stop, from budget to five-star
Quiet peninsula villages well off the usual tourist trail
What's Included
Seven nights’ accommodation at your selected hotels
Two nights in Chicago at the beginning of the journey
One night in Milwaukee
Two nights in Door County
One night in Madison
One final night in Chicago
Six-day rental car from Day 3 until departure
Automatic-transmission rental car in the selected category
Unlimited mileage where included in the selected rental rate
Rental-car taxes and standard inclusions shown during booking
Ability to choose or upgrade your hotels
Ability to add or remove nights
24-hour emergency assistance
What's Excluded
Flights unless added during booking
Transportation from the airport to your first Chicago hotel
Fuel
Road tolls and rental-company toll administration charges
Hotel, attraction and city parking charges
Wisconsin State Park vehicle admission passes
Optional excursions and attraction tickets
Additional drivers unless included in the selected rental rate
Optional rental-car insurance or equipment not included in the selected rate
Meals unless included with your selected hotels
Travel insurance
Personal expenses and gratuities
Any service not specifically listed under “What’s Included”
From per personUS$732