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2016 Chicago / Wisconsin Roadtrip

Long time readers will know that every year we embark on a US roadtrip. We pick a state at random and this year was the turn of Wisconsin. To access Wisconsin from Hong Kong, we chose to fly in to Chicago (direct flight with Cathay Pacific.. a mere 15 hours..) and then drive north.  I would have to say this year was one of my favourites. We lucked out with the weather (sunny but not too hot) and Chicago/Wisconsin has so much to offer. Another added bonus were the driving distances, on average only one to two hours.
Traveling with a 7 and 4 year old has its challenges. In a way I miss the days when we could bundle a toddler into a stroller and head off on a day’s sightseeing. Now they are more demanding and I have to tweak our itinerary to make it more fun for them and not all about me. But with older kids comes advantages, easier to eat meals out, no naps and later bedtimes and a greater appreciation for our surroundings.  I would recommend doing a US roadtrip for kids of any age. We have been doing them since our little one was 8 months old.
Where did we go in Wisconsin?
Typically I try to stick to one state but seeing as we were landing in Chicago, I couldn’t miss out on seeing the Windy City.  I used a mix of guidebooks, online resources, tourist boards and the kind contributors at Tripadvisor to pull together an itinerary.  We are used to road tripping and moving every few nights but if you are new to this, you may want to chill out and prolong your stays in certain places.
Our itinerary was as follows:
Chicago 4 nights
Milwaukee 2 nights
Madison 2 nights
Wisconsin Dells 1 night
De Pere/Green Bay 1 night
Baileys Harbour, Door county 2 nights
Sheboygan 1 night
We stayed in a mix of hotels and airbnb, all booked in advance.  It’s refreshing to mix up the accommodation. For example having access to more space and a kitchen in the airbnb rentals but then spend the night next in a hotel with a pool.
In retrospect I wouldn’t have tweaked any of our trip. It worked out perfectly and we managed to see nearly everything in my itinerary.  Coming off a longhaul flight, it’s always easier to have a few relaxing days in your first destination to acclimatise. Even better if you don’t have to drive.  Which brings me on to…
Car Hire Tips for a Roadtrip
  • We booked with Avis as the booking process is relatively hassle free and we can collect air miles (check which frequent flyer programme works best for you as this may vary)
  • The Avis website is extremely easy to use; you can make a reservation in 30 secs without paying and you only pay when you get to the car hire pick up.  We ended up changing the reservation a few days in advance and it was easy to do through our phone
  • We saved money through bringing our own child seats as our kids (age 7 and 4) are now in boosters.  We  used the Trunki Boostapak and also packed another booster in our checked luggage. We have had bad experiences in waiting around for cars with child seats so it was nice to know we had this in hand.
  • We decided not to hire a car from the outset in Chicago as downtown parking is expensive and local transport so convenient. It is also safer and less hassle not to have to hang around to organise the car hire when you’ve just landed from a 15 hour flight.  Uber is really useful for getting around a city, make sure you download the app.
  • We also decided to save money through buying a US Sim and not paying extra for a sat nav system. I have mixed feelings about this. Google maps is fantastic, particularly the traffic notification system. However there were times we were driving through rural Wisconsin with no signal and it was useless!
  • We do pay extra for Sirius XM as we love listening to the music and comedy channels on long drives.
  • In terms of entertainment in the car, we are an iPad free zone as our kids would never hand it back.  We take them to Walmart/Target and stock up on fun sticker books, activity toys and that usually keeps them happy.
  • Always buy insurance, don’t skimp on this. We have had prangs in the past an it’s not worth worrying about
  • You can also save money by opting out of the fuel purchase option.
  • Take photos/video the car as soon as you receive it so you can catalogue any blemishes.  same again when you arrive at car hire to return it.
  • Always factor in sufficient time to return your car rental at an airport.  On returning at Avis Chicago Airport, the airport transit bus then took about 40 mins to take us to the terminal! Luckily we weren’t in too much of a rush or I would have combusted.


What luggage did we take?
  • I took one big suitcase, a wheeled duffle and a hand luggage case.  For places where we only stayed one night, we would just pack up all our stuff in the hand luggage suitcase and leave the big bags in the car.
  • We also ended up buying an extra packable bag in Walmart for all our purchases!

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