West Town Chicago on Time Out Coolest Neighborhoods 2026

So I saw West Town made Time Out's coolest neighborhoods list at No. 18. Of course this happens right as we're considering moving there. We're in a two bedroom near the Western Brown Line stop and with our second kid on the way, we are bursting at the seams. We're totally priced out of a single family home here in Lincoln Square, and our realtor suggested looking in West Town. My fear is that this kind of press just means another round of price hikes. We drove around last weekend near Chicago and Damen and it already feels like Wicker Park South. Is it still a place for a family, or is it all just expensive restaurants and people who are out until 2 AM? We need good elementary school options and a yard that isn't a postage stamp. What's the reality of living there now, especially west of Ashland? Are property taxes as insane as people say?

Your "Wicker Park South" comment is spot on. I'm just north of the 606 and we've seen the spillover for years. All the new construction is skinny, million dollar single family homes. The traffic getting across North or Division to the Kennedy is a parking lot from 4 to 6 PM. If you want a quiet street you need to be looking west of Western, but even those prices are climbing fast. The 'cool' label is just marketing.

I live in Ukrainian Village, which is technically West Town, and I have to push back a little. Yes, it's expensive and some of the new places on Chicago Ave are a bit much. But the core of the neighborhood is still families, block parties, and people who have lived here for 30 years. We know all our neighbors. The kids play together in the street. You have to be realistic about the home prices, a turnkey SFH is going to start close to a million, but you can still find two and three flats with yards that have good bones if you look. Our local CPS school has a really active parent group and there's a good mix of families who choose it and others who do private. It feels more grounded than the Time Out article would have you believe. You just have to get off the main drags like Damen.

I read these threads and just shake my head. Number 18 coolest? For what you'd pay for an old house with no parking in West Town, you could get a brand new 3,000 square foot house with a two car garage and a big yard out here. And my property tax bill is probably what you pay for a month of daycare. Good luck with the dibs fights this winter.

That ranking is a joke because West Town is like five different neighborhoods. The vibe at Grand and Western is totally different than near the Blue Line stop on Division. That said, my property tax assessment just came in and the 'cool' factor is definitely hitting my wallet. My advice, look at the school boundaries very, very carefully. They can zig zag in ways that make no sense. A house on one side of the street can be zoned for a great school and the one across from it is not.

Thanks for all the different perspectives. WickerParkJen, your point about the community feel is what we're looking for, but the prices are just tough to swallow. We looked at a few listings online after your post and you're right, anything updated is already at the absolute top of our budget. And OakLawnTony, your comment hits home more than you know; we have that exact city vs suburbs debate every night. We're thinking we might need to expand our search north to Avondale or Portage Park to find a balance between space and city access.

Liz, if you're looking in Portage Park, you'll find a lot of families who made the same calculation. We moved from Logan Square five years ago. You get a bungalow with a yard for the price of a condo in West Town. We have actual parking. It's not 'cool' like Time Out means it, there are not a ton of trendy bars, but it's a solid, quiet neighborhood with a huge park and good schools. You just have to decide if you're okay with driving a little more for your nights out.