My buddy and I are flying one way to Milwaukee and driving up play Whistling Straits (both Irish and Straits courses), Blackwolf Run (River and Meadows courses) and then driving down to Chicago and playing Cog Hill #4 before flying back out of O'Hare. Does anyone have any tips for the courses or recommendations for things/places we should check out during our trip? We only plan on a caddy for the Straits and River course.

I went with my dad in 2019 Memorial Day weekend. I'm not sure if y'all have time but I loved Erin Hills and it's only 45 minutes outside of Milwaukee. We stayed in the third ward in Milwaukee and there's a decent amount of stuff to do. Went to the Milwaukee Ale House, Public Market, and the Harley Davidson museum.

I only played Whistling Straits at Kohler but depending on the wind, the lake won't come into play as much as you would think. Every par 3 is similar in that they sit on the edge of the lake with a steep drop off. TV doesn't do the 17th justice, it's a very intimidating shot. The 5th hole where Bryson took that ridiculous line was one of my favorites.

Not sure how long you're in Chicago but I could probably start a whole thread on things to do there. I'm not necessarily a huge art guy but the Art Institute of Chicago is awesome. It's in Millennium park near the bean.

Try to work in Erin Hills

Stefanos Italian in Sheboygan was pretty good.

I'll third Erin Hills. I played 36 holes there last summer with my dad and it was amazing. I'm itching to get back.

Definitely considered Erin Hills but couldn't find time on the trip to fit it in. We are flying in on a Wednesday and flying out Sunday. Thursday playing Whistling Straits courses, Friday playing Blackwolf Run, and the Saturday playing Cog Hill. Only way we could make it work is drive straight to Erin Hills Wednesday when we land and play an afternoon round. We planned on just driving to Koehler that day and playing a par 3 course to get some swings in.

Fly in Wednesday, play Erin Hills & stay on property if you can. I bet it'll be the highlight of your trip. Regardless, you won't regret it. Drive to Kohler next AM.

I'll 4th Erin Hills. Did that trip and it was by far my favorite of the 5 courses and it wasn't close. Have had several buddies thru the years plan trips similar to yours with no EH on the itinerary. I've pleaded with them to not skip EH and the ones that figured out how to work it in thanked me endlessly when they got back. Don't make the mistake. Blow off Irish and/or Meadows if you have too. Good courses but not even in the same league as Erin or the other 2 Kohler courses.

I mentioned in my 1st post but I'll be another to hammer home Erin Hills. One of my favorite courses I've ever played and I enjoyed it more than Straits.