By Sam S.

The North Shore is a 30-mile stretch of lakefront suburbs north of Chicago that people either move to on purpose or end up in after their second kid. The four towns most commonly debated — Wilmette, Winnetka, Highland Park, and Glencoe — are all on the Union Pacific North Metra line, all have lake access, and all have property taxes that will make you reconsider your choices at least once a year. But they are not the same place, and the differences matter depending on what you actually want out of life.

Wilmette is the most accessible of the four, which in North Shore terms means "you can theoretically afford it." The median home price hit $1.224 million in April 2026, which is still a lot of money, but it's the floor of the neighborhood rather than the ceiling.

The Metra situation is straightforward: Union Pacific North from the Wilmette station gets you to Ogilvie Transportation Center in about 30 to 35 minutes. That's a reasonable commute by Chicago standards, which is to say it's manageable if you've mentally committed to the suburb life and you own a good pair of headphones.

Wilmette Beach on Lake Michigan is open to residents with a sticker. The beach is real and usable, not a decorative strip of sand you can't touch. Schools are strong across the board, feeding into New Trier High School, which is the significant thing to know about Wilmette from a district-line standpoint.

Property taxes on a median home run somewhere between $18,000 and $22,000 per year. That number surprises people who are new to the North Shore. It should not be a surprise. Budget for it from the start.

The Baha'i Temple is in Wilmette, and it's worth seeing — a 135-foot domed structure on Sheridan Road that looks like nothing else in the Chicago area. It functions as an actual house of worship, not just a landmark, which is worth knowing before you plan a full Saturday around it.

Winnetka is what happens when a suburb decides that a conventional downtown is optional. There isn't really one. The commercial areas are spread thin across the township, and if your definition of a good suburb includes the ability to walk to a restaurant on a Tuesday night, Winnetka may frustrate you.

What Winnetka has instead is New Trier High School, which is regularly rated among the top public high schools in the country. For families with kids in or approaching high school, this is a significant pull. For everyone else, it's a selling point that doesn't do much work in daily life.

Three Metra stops serve Winnetka on the Union Pacific North line: Braeside, Winnetka, and Indian Hill. The commute to Ogilvie runs roughly 35 to 40 minutes depending on the stop. The median home price falls in the $1.3 to $1.5 million range, making it noticeably more expensive than Wilmette without offering dramatically more in the way of amenities.

Winnetka is quiet. Very quiet. If you have school-age kids and money and value peace, it's probably excellent. If you don't have kids yet or your kids are grown, you may find yourself driving to Wilmette or Highland Park to do anything.

Highland Park has a downtown. An actual one, with restaurants, bars, independent shops, and a usable main street that sees foot traffic on weekday evenings. This is not a small distinction — it changes the daily texture of living there in ways that are hard to quantify but easy to feel.

The Metra commute from Highland Park station to Ogilvie runs about 45 to 50 minutes on the Union Pacific North. That's the longest of the four suburbs covered here, and it's worth factoring in honestly. An hour on the train each way is a different lifestyle than 30 minutes each way.

Ravinia Festival is in Highland Park — an outdoor venue that hosts classical music, pop, and jazz concerts from June through September. Residents treat it as a backyard amenity. You bring a blanket, a bottle of wine, and you sit on the lawn for the Chicago Symphony Orchestra. It's one of the better things about living in the northern suburbs.

Lake access comes through Rosewood Beach, resident only.

The price range in Highland Park is more varied than the other three towns. Entry points exist around $500,000 to $600,000 for condos and smaller homes. The upper end goes well past $2 million. This spread means Highland Park attracts a wider demographic mix, which shows up in the character of the town in ways that are generally positive.

The high school here is Deerfield High School, which feeds from Highland Park and Deerfield. It ranks in the top 20% in Illinois — a strong school, not a New Trier-level brand name, but a good outcome for most families.

Glencoe is the smallest of the four and the one that most fully leans into the idea that a suburb can be almost entirely residential. There is a modest commercial district, but it's not a destination. People who live in Glencoe mostly seem to have made a deliberate choice to live in a place that is not trying to be anything other than what it is.

The Union Pacific North stop is Glencoe station, roughly 40 minutes to Ogilvie. The median home price runs in the $1.2 to $1.5 million range, but entry points at the lower end of that range are hard to find. The housing stock skews large and the turnover is low.

The Chicago Botanic Garden is technically in Glencoe — the address is Glencoe, and the main entrance is off Green Bay Road in the town. It's a 385-acre public garden that draws visitors from across the region. Glencoe residents don't need to drive far to get there, which is a genuine perk.

Glencoe is in the New Trier High School district, along with Wilmette and Winnetka. For buyers who are prioritizing that school district and want the quietest, most residential environment of the three New Trier towns, Glencoe is the answer.

If you want the lowest entry price and a straightforward commute, Wilmette. If the New Trier district is the main variable and you want a town with some walkable life to it, Wilmette still wins over Winnetka. If you want a real downtown and you can tolerate the longer train ride, Highland Park is the only one of the four that actually has one. If you want the most exclusive feel and the quietest possible environment and money is not the binding constraint, Glencoe.

New Trier versus Deerfield is the most common conversation in this comparison, and the honest answer is that both schools produce good outcomes. New Trier has the reputation and the resources. Deerfield is strong. The school question should not be the only question.

Property taxes across all four towns are high. That is not going to change. Price them into your mortgage math before you fall in love with a house.

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