Not really, but historically speaking there’s a solid sibling rivalry between Madison and Milwaukee.
Milwaukee is walkable in a sense…but like if you live in the 3rd Ward, things are walkable there but you might not walk to the East Side - you’d drive there. I enjoyed living downtown when we did but still often drove to different areas of the city for food, etc.
I have only visited Madison, but always enjoyed my time there. Good food, drinks, etc.
What are you ultimately looking for? We live in a suburb of Milwaukee and if you don’t go during rush hour, I can get downtown in 20 minutes. It’s easy to get in and out and enjoy the city while also having a house and yard.
That’s good to know! I’ve lived north of Atlanta for ~12 years. On a good day, getting downtown takes me roughly 40-45 minutes in stop-and-go traffic. Public golf is slow/not great. No food culture around me, which stinks. It’s mostly closer to the city.
I’ve never lived in a downtown area where walking was truly an option, so my wife and I want to try it out before we decide to buy another place in the burbs.
Milwaukee would be more walkable I think? Downtown is bigger a least and the population is 2x.
I love Madison. I love Milwaukee.
MKE feels quite a bit more urban, in a humble midwestern way. Madison is more a big college town to me. In terms of “being a two hour drive from…” I think they’re both great locations to cool stuff and lots of the beauty of the state.
Neither is as walkable as Chicago. ducks
Reading this, if you’re not considering Chicago, I’d do Milwaukee. Seeing that you travel for work as well, being a bit closer to Ohare is probably a good thing.
Chicago is under consideration as well. I historically have liked big cities to visit, but had a hard time seeing myself living there. Some of that could be that I’ve never lived downtown, and always associate “big” with Atlanta traffic.
Everyone I’ve spoken to loves it there, though.
if you’re looking to avoid traffic, Chicago is absolutely not the pick
Yeah people like Chicago because of the neighborhoods which makes it feel a bit less like a big city, and the people are generally friendlier than big cities on the east coast, and it’s cleaner… but as the Sconnies will undoubtedly say, “not as friendly us and likely more obnoxious when out and about than the cheeseheads!*”
*debatable
Everything you said is true.
And like any sibling rivalry, Milwaukee doesn’t even acknowledge it or really know it exists.
The Milwaukee Parks system has one of the best public golf programs in the country. I have no idea what Blake is fucking talking about. Then you get a host of non-municipal options that are fine, a shit load of great private courses, and you’re in the middle of Kohler, Sand Valley, Erin, Lawsonia (which are all super manageable day trips).
My parents lived in Marietta for 20 years and I went to UGA…
Milwaukee, Madison, Chicago aren’t even close to Atlanta from a traffic perspective. You can maybe argue Chicago, but the public transit in Chicago is miles beyond Atlanta.
Milwaukee is a smaller, more manageable version of Chicago/Atlanta. Food is better in those cities, but Milwaukee has some places that fight above it’s weight (ducks). Madison is Athens if it had a Capital. Cheaper, much more laid back vibe and less big city feel than Milwaukee.
Traffic sucks… but walkable!
Atlanta is way worse and I will die on that hill.
If you’re claiming those as MKE, then I can claim them for NE Wisconsin too (since most of them are much closer to us).
You can have Kohler though, that’s not really public golf.
Than where? The fox valley? Dane is typically 2 or 3 behind Ozaukee and Waukesha counties for most expensive places to live.
Agreed on all accounts. Except Erin.

Strike that. I feel like you can buy a house in Madison for cheaper than Milwaukee?
Very helpful — thanks so much!
I lurk on here as a Chicago resident with Wisconsin ties, Madison and Milwaukee are great cities.
Follow up ask -
Are you a high rise/door guy, single family home, 2 flat/condo type of person? I was never a high rise person if the downtown aspect is a concern regardless of Madison, MKE, Chicago. Madison and MKE may have more of a mix in the heart of the city but not in Chicago.
Like @TeddyPargame and @mikedabomb are referencing, I’m on the northwest side of Chicago in a SFH where we have our more intimate neighborhood and neighboring pockets with access to the city train to get downtown as well as Metra that gets in to south of Milwaukee (extend the line!) or to downtown Chicago as well, I’m near I90/94 for getting to O’hare or Midway, but I94 makes it easy to fly out of Milwaukee and frequently visit for concerts, games, and visit my family. If closer to downtown Chicago, that traffic grows exponentially at all days and hours - I lived in KC where downtown was typically dead and traffic was often worse in suburbs.
MKE parks golf are solid, in Chicago you are playing one of a couple shaggy 9s or Jackson Park 18 really early (or enjoy a 4 hr 9) or driving to the burbs and the drive back stinks.
Don’t worry about the cold in Wisconsin or Chicago, your diet will help thicken up your blood and adjust.
Urban = Stolen Kias, shootings, etc. (and before I get criticized, I’m originally from one of the five boroughs of NYC during the crack epidemic)
It really just means big buildings, but sure.
Great info — to answer the high rise question: I don’t know the answer. I grew up on a farm, and currently own a single family home on an acre.
In all honesty, in my head I picture living that high-rise downtown life to try something “new” and then buying a place outside the city if we like it enough within a few years.
I’m kind of in “itch scratching” mode right now.
We don’t have any children (no plans to either), so not moving in my 30s whenever we’re able to seems like a missed opportunity at the moment.
My wife always wanted to rent in a high rise just to experience it, sounds like you have the opportunity. You’ll be giving up control - which you would mostly as a renter of course- which I struggle with so we bought a condo in a smaller/medium older/rehabbed building on the northside at first where I quickly took over the HOA.
The fine folks of Wisconsin here can address MKE and Madison, but in Chicago if you want that downtown downtown, you’ll be high rise unless you head to one of the neighborhood’s Teddy references.