Wednesday can't come soon enough!

This year my group will be driving from Milwaukee to Indy. We're hoping to leave in the morning.

Does anyone have any tips on timing or routes to avoid/minimize Chicago morning rush hour?

Already saw the great thread about I-65, but wasn't sure about the first leg of our journey.

Any help is greatly appreciated!!

I would say leave no earlier than 0900am. If you leave between 9-10am, you should hit the late-morning/early afternoon sweet spot on 294 around Chicago when traffic is relatively low since all the business hours workers have started their day and the first-shift workers don't get off till 2:30-3:30p. 

Leaving much earlier might get you there before the hotel will officially let you check in anyway.

Question for people that know the area: Would the best first leg be I-94, or I-294?

I have dim memories from a job long ago that there was debate among our staff on which route was best. That business traveled north to Milwaukee regularly. I can't recall I-294 trips, but I do remember getting slowed to a crawl at times on I-94. 

I will say this: Regardless of whether it's I-294, 94, 290, or 90, I strongly recommend hitting I-65 to get to Indianapolis. Google maps show some alternate routes involving state highways, and IMO those would just add time and confusion to the trip. Even when I-65's construction (https://511in.org/, click on the "Construction" checkbox) is taken into account, I'll bet it's the shortest, most pain-free route to just grin and bear the construction zones. 

I94 goes pretty much straight through Chicago, while 294 goes around it through the suburbs. Even before the days of blindly following wherever Google tells me to go, when I would drive to Wisconsin from Michigan I would always take 294 unless I specifically wanted to stop somewhere in Chicago on my way there or if there was known construction.

So I guess I would say typically 294 is the better route if you are just going around Chicago. Though both get hairy during rush hour.

Get an I-pass and save 50% on tolls.  You can get one at any Jewel store, I think.  You do need to go online to activate it though.

I drive from north of Milwaukee to Indy every year.  I always take 294 and hitting there right around 10 or so is a decent time.  I just try to avoid 7-9 and 3-6.   Of course, hitting Chicago at that time means you are leaving Milwaukee around 8 or so and you are hitting Milwaukee (and don't need to tell you that Milwaukee construction stinks right now)

I stopped driving to Indy on Wednesday and started leaving Tuesday nights and just driving to Rensselaer and crashing there overnight and finishing the last 2 hours to Indy.   Extra hotel night, but cheaper and I'm avoiding Chicago rush completely as I'm hitting it around 8PM. 

As a note, without an I-pass, you will need to pay the tolls online as they don't do cash at tolls now.

Thanks everyone, this is exactly the kind of advice I was looking for! See you soon!!

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