Discovering Vacation Home Hotspots: Where Chicagoans Dream of Escaping (And How Our Spots Stack Up)

Vacation home hotspots are like the ultra-rare Pokémon of real estate: everybody wants them, few can catch them, and even fewer can maintain them without shedding a tear or two over property taxes. As Chicagoans, we’ve got our own little slice of getaway heaven in places like Lake Geneva and Michigan’s Harbor Country. But how do these Midwestern retreats compare to the flashier, more exotic vacation markets that make headlines and Instagram reels nationwide? Let’s dive into it.

The West Coast Show-Offs:

First, you’ve got Malibu and Big Sur. Oh, Malibu, with its celebrity mansions perched dramatically on cliffs like a movie star brooding over their next blockbuster flop. Homes here don’t just come with ocean views—they come with price tags that would make even a seasoned real estate investor gulp. The median home price in Malibu hovers around $3.6 million, while in Big Sur, properties average well over $2 million. Sure, these places scream “luxury,” but they also scream “mortgage payment that makes you cry into your kale smoothie.”

Now compare that to our beloved Lake Geneva. True, you won’t spot George Clooney sipping a matcha latte on the dock, but you might see a friendly family grilling brats, which is honestly way more relatable. In Lake Geneva, median home prices are around $500,000, though lakefront properties can climb into the millions. While the California coast may have dramatic Pacific sunsets, we’ve got sunsets over shimmering lakes and the kind of summer festivals where you can eat fried cheese curds and call it a cultural experience.

The Mountain Marvels:

Aspen, Park City, Jackson Hole—these ski towns have a charm that makes you want to throw on a cashmere sweater and drink hot cocoa in a lodge that probably costs more than your actual home. Aspen’s median home price is a staggering $9.5 million, while Park City’s median is a slightly more “affordable” $1.9 million. Jackson Hole, famous for its rugged beauty, comes in at a median of around $3 million.

But don’t count out Harbor Country. Sure, we don’t have mountains, but we’ve got dunes that’ll give your legs a workout (and maybe even make you feel athletic for once). Instead of après-ski, we’ve got après-beach—where a sunburn pairs perfectly with a locally brewed beer. Plus, our friendly Midwestern charm means you can chat with your neighbors without feeling like you’re auditioning for the Real Housewives of Lake Geneva. And the median price? Harbor Country’s homes generally range from $300,000 to $750,000, with lakefront properties fetching over $1 million.

The Sunshine State Stunners:

Florida’s coastlines—Naples, the Florida Keys, and the ever-glamorous Palm Beach—are perennial vacation home darlings. They boast year-round warmth, sandy beaches, and enough palm trees to make any snowbird’s heart flutter. Naples, for example, has a median home price of about $800,000, while Palm Beach easily hits $1.5 million or more. The Florida Keys, known for their laid-back vibe and stunning sunsets, have a median price of $1.2 million.

Meanwhile, our local getaways have a certain charm that doesn’t require a three-hour TSA line. You can hop in the car and reach the shores of Lake Michigan in just a couple of hours. And you know what’s waiting there? Not just sandy beaches, but also quaint shops, farm-to-table restaurants, and wineries where you can sample a cabernet without having to take out a second mortgage. Median prices for homes in Southwest Michigan’s lakeside communities range from $300,000 to $600,000, making them more accessible than their Florida counterparts.

The Verdict:

Vacation home hotspots might look glamorous on HGTV, but there’s something delightfully unpretentious about Chicago’s nearby retreats. While the national hotspots flaunt their scenic drama and high price tags, our Midwest gems offer the kind of laid-back comfort that feels more “come as you are” than “pretend you’re a millionaire.” So, whether you’re chilling on a pier in Lake Geneva or sipping wine in Harbor Country, remember: home is where the heart (and the affordable waterfront property) is.

Sources:

• Zillow: Malibu, Aspen, Naples, and Jackson Hole market data (2024)

• Midwest Real Estate Data (MRED): Chicago-area vacation home prices

• Realtor.com: Big Sur and Park City median home values (2024)

• Redfin: Harbor Country median home prices (2024)

• Local real estate listings and brokerage reports for Lake Geneva and Southwest Michigan (2024)