If you're a Chicago resident dreaming of a weekend getaway or considering investing in a second home, you're not alone. Thousands of Chicagoans have already made the leap, creating a thriving second home market in several key destinations within driving distance of the Windy City. But where exactly are most Chicagoans buying their second homes, and what makes these locations so appealing?
The Top Second Home Destinations for Chicagoans
Wisconsin: Lake Geneva and Beyond
Lake Geneva stands as the crown jewel of Chicago's second home destinations, earning the nickname "Newport of the West." Located just 65 miles northwest of Chicago, Lake Geneva has been home to numerous lakefront mansions owned by wealthy Chicagoans as second homes since the late 19th century. The area offers:
- Drive time: Just over 2 hours from downtown Chicago
- Premium waterfront properties: Recent sales include homes selling for $20 million in June 2025, with the property going under contract in just three days
- Luxury amenities: Private beaches, golf courses, and upscale dining
- Investment appeal: Home prices in Walworth County were up 18.3% at the end of April 2024 from the previous year
Beyond Lake Geneva, other Wisconsin destinations gaining popularity include:
- Twin Lakes near the Illinois border
- Delavan Lake for more affordable options
- Door County on the Green Bay side
- Wisconsin Dells region
Michigan: Harbor Country and the Southwest Shore
Southwest Michigan, particularly the "Harbor Country" region, represents the second most popular destination for Chicago second home buyers. Michigan locations like New Buffalo, Grand Beach, and South Haven seem to be the preferred second-home locations for Chicagoans, offering metropolitan amenities attractive to entrepreneurial-minded individuals.
Key Michigan destinations include:
New Buffalo - This charming town, located only an hour and 10 minutes away from Chicago, boasts a large boating community marina on the shores of Lake Michigan, offering plenty of beaches, shops, restaurants and nightlife
Other Popular Michigan Towns:
- Lakeside - Known for modern architectural homes
- Three Oaks - Growing in popularity with quicker sales
- St. Joseph - Offers variety in residential options plus dining scene
- South Haven - Traditional favorite with beach access
- Saugatuck - Upscale resort community
Indiana: Beverly Shores and Michigan City Area
Northwest Indiana offers Chicago residents proximity to Lake Michigan with potentially more affordable options. Chicago buyers are looking at Indiana, where they can be close to Lake Michigan, beaches, harbors, golf courses and tennis courts, with proximity that gives them the ability to drive out there on a lovely evening and be back at work the next morning.
Popular Indiana locations include:
- Beverly Shores - Unique lakefront community
- Michigan City area
- LaPorte County developments like Tryon Farm
Illinois: Northwest Counties
More and more Chicagoans are venturing to Jo Daviess and Carroll counties in northwest Illinois, featuring three private lake communities with second homes, recreational properties and full-time living opportunities. These include:
- Apple Canyon Lake
- Lake Carroll
- Galena Territories
- Galena - Historic town with charm and affordability
Market Trends and Investment Considerations
Current Market Conditions
The second home market near Chicago has experienced significant changes:
Inventory Challenges: The inventory shortage is particularly acute in the A tier of locations, which are typically on water, whether it's Lake Michigan, Geneva Lake or Green Bay
Price Trends: In the state line-to-Bridgman stretch of Michigan lakefront, which includes New Buffalo, Lakeside and other popular second-home towns, sales numbers are down but prices continue rising
Fast Sales: Properties in prime locations are selling incredibly quickly. Two multimillion-dollar mansions in Lake Geneva both landed buyers a few days after hitting the market in September 2025
Why These Locations Appeal to Chicagoans
Proximity: All top destinations are within 2-3 hours of Chicago, making weekend trips feasible
Remote Work Impact: COVID blurred the line between primary and secondary residences, as people realized if they can spend more of their week at their vacation home when they don't have to get to downtown Chicago
Lifestyle Purchases: Unlike buyers of first homes, second-home buyers are looking to buy a lifestyle, not just shelter
Water Access: Lake Michigan and inland lakes provide boating, swimming, and recreational opportunities
Price Ranges and What to Expect
Budget Tiers
Entry Level ($200K-$500K):
- Inland properties in Wisconsin and Michigan
- Condos and smaller homes away from prime waterfront
- Northwestern Illinois lake communities
Mid-Range ($500K-$1.5M):
- Properties closer to water but not directly on it
- Larger homes in established communities
- Updated cottages in prime locations
Luxury ($1.5M+):
- Direct waterfront properties
- Waterfront homes are a limited commodity, and demand has intensified as "rich people are richer than they used to be"
- Architectural estates and new construction
Market Realities
Competition: In May 2025, a real estate agent had one listing bring in eight offers and another bring in five offers
Limited Inventory: Before 2020, it was typical to see about 300 homes on the market each year in the roughly 20-mile stretch of lakefront southwest Michigan, but "for the past year and a half, we've been under 100"
Tips for Chicago Second Home Buyers
Best Strategies
- Move Fast: In hot markets like Lake Geneva and Harbor Country, desirable properties sell within days
- Expand Your Search: Consider locations slightly beyond the prime zones for better value
- Work with Local Agents: Choose realtors specializing in second homes who understand the market
- Be Prepared Financially: Have financing pre-approved and be ready to make strong offers
Emerging Areas
Real estate professionals note growing interest in:
- Coloma, Michigan - 38 miles north of New Buffalo
- Door County's Green Bay side - More affordable than Lake Michigan shore
- Small Wisconsin lake communities - Outside the Lake Geneva premium zone
The Future of Chicago's Second Home Market
The second home market for Chicagoans shows no signs of slowing. Remote work flexibility has created a "culture shift" where people can spend more time at their second homes, making the investment more valuable. With inventory remaining tight and wealthy buyers continuing to seek lifestyle properties, prices in prime locations are expected to remain strong.
Whether you're looking for a weekend retreat, an investment property, or planning for retirement, understanding where most Chicagoans are buying can help inform your decision. The key is acting quickly when the right property comes available and working with agents who understand these unique markets.
Looking to buy a second home near Chicago? Let me connect you with one of my partners so you have experienced local real estate agents in Lake Geneva, Harbor Country, or other popular destinations to start your search. The perfect weekend getaway might be closer than you think.
