Need Advice - Chicago Area Overnight with Boat on Trailer

YYZRC

Purchased a 28' Four Winns from SkipperBuds Pewaukee and will be trailering it next week from Pewaukee to Georgian Bay.

Can anyone recommend a safe city to overnight outside of Chicago?

skennelly

Will you be getting a hotel?  What point of the leg do you want to overnight?  North or South of the city?

skennelly

You'll be fine any place off of 294 but not past 80...it can get a little sketchy in some areas.

YYZRC

Definitely a hotel. Was thinking east of Chicago. Thoughts on Stevensville (Michigan)?

skennelly

I'm not familiar with Michigan.  New Buffalo is a nice area

YYZRC

Thank you! 

randy56

Stay away from Michigan City, and congratulations. 

skennelly

Agree with @randy56.  New Buffalo would be a great area in my opinion

oscar1

pass Chicago during the day light

skennelly

His route is 294 that goes around the city...not through it.  You are totally safe on 294.  All the shootings ect...are on the expressways through the city.  Eisenhower and Dan Ryan avoid at night.

mattie

@YYZRC which Four Winns model? Curious minds….

Long haul home. Take lots of tools etc. Trailer probs are likely if used equipment.

YYZRC

Its a 268 - same as my first boat!

Definitely will be prepared for the worst.  I'm having a mechanic inspect the trailer before we pick it up so hopefully nothing crazy, but it is 15 years old.

TonyG13

New tires for sure before it rolls.

YYZRC

Loaded and rolling!

mattie

@YYZRC go easy YYZ you are maxed out for towing with the 350.

That 268 would be 6500 pounds + trailer. Give yourself lots of room for go/stop.

YYZRC

Yeah it’s at the limit for sure. It’s a 53 though so good brakes!

oscar1

Have a safe trip

aero3113

@YYZRC , are you going to use it or flip it?

Cableguy Greg

If you run into any issues, I am an hour and a half south of Chicago. I can be of assistance if needed. Safe travels to you!! 

YYZRC

Flip in spring. In Detroit now. 

YYZRC

Thanks @Cableguy Greg ! We made it to the border.