Chicago to Connecticut

As an alternative you could take 90 all the way into western MA and then drop down rt 8 (via Rt 20 through Lee MA). Rt 8 will take you straight to bridgeport which is right next to milford. According to google its ~80 more miles (i did generic Joliet IL to Milford CT) but you avoid all the BS. Tolls are going to be a wash either way, since you'll be paying both ways on the Cuomo Bridge (I-287 about $24 each way) and the Delware Water Gap ($22) going outbound vs the Thruway (70ish) and the small bit of the MA pike(about $2). You wont hit any real traffic until Waterbury CT, and depending on time of day you may just sail right on through.

 

Seeing as the OP is from Chicago I think he could deal with a bit of traffic versus going upwards of 100 miles out of the way. Keep the route simple if you're not familiar with the area.

JMHO
JD

 

According to the I-Pass website I-Pass is accepted at EZ-Pass toll facilities.

JD

 

Just to give you an idea...........if you run over the Tappan Zee before or after rush hour you should be in Milford in less than an hour and a half from the NJ/NY state line. FYI Ct has a scale just past the NY/CT state line on 95.

JD

 

Yes.

 

80/287North/287East/95 North to Milford


@jdchet knows the deal
Traffic is traffic.
I ran 95 at 287 to route 25 19 times each way this week-
You’re gonna hit traffic. You’ll be fine.