Easy Summer Road Trips from Chicago: 7 Weekend Getaways Worth the Drive
Looking for an Easy Road Trip from Chicago?
One of the best things about living in Chicago is how many incredible destinations are just a short drive away. Whether you're looking for beaches, hiking, boating, boutique shopping, charming downtowns, or a long weekend escape, the Midwest offers countless options within a few hours of the city.
Here are seven of our favorite summer road trips from Chicago, ranging from quick day trips to memorable weekend getaways.
1. Indiana Dunes, Indiana
Drive Time: Approximately 1 Hour
For those craving nature without a long drive, Indiana Dunes is one of the easiest escapes from Chicago. Located along Lake Michigan's southern shoreline, the park offers towering sand dunes, scenic hiking trails, and miles of beautiful beaches.
Don't Miss:
Mount Baldy and dune trails
Lake Michigan beaches
Chicago skyline views from the shoreline
Why We Love It
It's hard to believe such dramatic natural scenery exists just an hour from downtown Chicago. It's perfect for a day trip with hiking, swimming, and sunset views.
2. Lake Geneva, Wisconsin
Drive Time: Approximately 1.5 Hours
Lake Geneva has long been a favorite getaway for Chicagoans. Once a retreat for wealthy Chicago families during the Gilded Age, the lake remains known for its grand estates, waterfront dining, boating, and walkable downtown.
Don't Miss:
The 21-mile Lake Geneva Shore Path
Historic lakefront mansions
Boat rentals and lake cruises
Lunch at Gordy's Boat House
Why We Love It
The combination of lake views, charming shops, historic architecture, and easy accessibility makes Lake Geneva one of the most popular weekend destinations near Chicago.
3. New Buffalo, Michigan
Drive Time: Approximately 1.5 Hours
Located in Michigan's Harbor Country, New Buffalo offers a relaxed beach-town atmosphere with boutique shopping, waterfront dining, and beautiful Lake Michigan beaches.
Don't Miss:
New Buffalo Public Beach
Harbor Country boutiques
New Buffalo Marina
Rooftop dining at The Stray Dog
Why We Love It
New Buffalo feels like a true vacation destination without requiring a flight. It's ideal for a spontaneous summer weekend.
4. Milwaukee, Wisconsin
Drive Time: Approximately 1.5 Hours
Milwaukee combines lakefront scenery, great food, historic architecture, and a thriving arts scene into one easily accessible destination.
Don't Miss:
Milwaukee Art Museum
Historic Third Ward
Milwaukee Public Market
Lakefront Brewery and local beer gardens
Why We Love It
Milwaukee delivers the energy of a city getaway while maintaining a laid-back Midwestern feel.
5. Saugatuck, Michigan
Drive Time: Approximately 2.5 Hours
Known for its art galleries, coastal charm, and beautiful beaches, Saugatuck is often considered one of the most picturesque small towns on Lake Michigan.
Don't Miss:
Oval Beach
Downtown art galleries
Shopping and local boutiques
Dinner at The Southerner
Climb Mount Baldhead for panoramic views
Why We Love It
Saugatuck offers a unique blend of beach town, arts community, and small-town charm that keeps visitors coming back year after year.
6. Door County, Wisconsin
Drive Time: Approximately 4.5 Hours
Often called the "Cape Cod of the Midwest," Door County offers waterfront villages, scenic cliffs, state parks, wineries, and some of the most beautiful shoreline in the region.
Don't Miss:
Cave Point County Park
Peninsula State Park
Fish Creek
Local cherry orchards
Cherry pie from Bea's Homemade Products
Why We Love It
Door County feels like an entirely different world, making it one of the Midwest's premier summer destinations.
7. Mackinac Island, Michigan
Drive Time: Approximately 6 Hours (plus ferry ride)
One of the most unique destinations in the country, Mackinac Island offers a step back in time where cars are replaced by bicycles and horse-drawn carriages.
Don't Miss:
The island's famous 8-mile perimeter trail
Horse-drawn carriage tours
Historic downtown
Mackinac Island fudge
Why We Love It
Few places feel as special and timeless as Mackinac Island. It's an unforgettable destination for a long summer weekend.
Frequently Asked Questions About Road Trips from Chicago
What are the best day trips from Chicago?
Some of the best day trips from Chicago include Indiana Dunes, Lake Geneva, New Buffalo, and Milwaukee, all located within approximately 90 minutes of the city.
What beach towns are near Chicago?
Popular beach towns near Chicago include New Buffalo, Saugatuck, Lake Geneva, and communities throughout Door County.
What are the best weekend getaways from Chicago?
Door County, Saugatuck, Mackinac Island, and Lake Geneva are among the most popular weekend getaway destinations for Chicago residents.
What is the closest national park to Chicago?
Indiana Dunes National Park is located approximately one hour from Chicago and offers hiking, beaches, and scenic views of Lake Michigan.
What is the best family-friendly road trip from Chicago?
Indiana Dunes, Lake Geneva, Door County, and Mackinac Island all offer activities suitable for families, including beaches, parks, biking, boating, and outdoor recreation.
Busby Group Perspective
One of the reasons so many people love living in Chicago is the ability to enjoy world-class city living while having access to incredible weekend destinations throughout the Midwest. Whether you're heading to Lake Geneva for the day, spending a weekend in Harbor Country, or exploring the shores of Door County, these destinations make it easy to enjoy summer without getting on a plane.
Many Chicagoans eventually find themselves exploring a second home, vacation property, or investment opportunity in one of these markets. Others discover a destination they love so much that it inspires a future move.
Through our nationwide network of vetted real estate professionals, we can connect you with trusted local experts in each of these destinations, including Wisconsin, Michigan, Indiana, and beyond. Whether you're considering a lake house, vacation rental, investment property, or a full-time relocation, we're happy to help guide the process and make the right introductions.
If you're thinking about a second home, investment property, or a move to a new market, don't hesitate to reach out. We're always happy to be a resource.
Securing an Off-Market New Construction Home
An out-of-town Houston Astros player wanted a low-maintenance home in Chicago where his family could stay while visiting the city. As Midwest natives, they wanted an exceptional location with the convenience of new construction.
Using our development experience and industry relationships, we identified an off-market new construction home that allowed the family to personalize select finishes before completion.
The result was a beautiful, low-maintenance home that perfectly fit their lifestyle. When it came time to sell, we helped them maximize their investment and achieve a strong profit.
Highlights:
Off-market new construction opportunity
Buyer customization options
Low-maintenance luxury living
Sold for a strong return
Busby Group Named Among the Top 1.5% of Real Estate Professionals Nationwide by RealTrends Verified
Busby Group Earns RealTrends Verified Recognition for 2026
Busby Group is honored to once again be recognized by RealTrends Verified, earning a place among the top 1.5% of real estate professionals nationwide based on 2025 sales performance.
This annual ranking recognizes the highest-performing agents and teams across the United States based on independently verified sales volume and transaction sides.
You can view our RealTrends Verified profile here:
https://www.realtrends.com/team-profile/busby-group-illinois-compass/
Busby Group RealTrends Verified Rankings
According to RealTrends Verified, Busby Group achieved:
$86.94 Million in Sales Volume
106 Transaction Sides
National Ranking #376 by Volume
National Ranking #654 by Sides
Illinois Ranking #15 by Volume
Illinois Ranking #30 by Sides
Average Sales Price: $820,200
These results earned Busby Group recognition as both a:
RealTrends Verified Top Team by Volume
RealTrends Verified Top Team by Sides
What Does the RealTrends Verified Top 1.5% Ranking Mean?
RealTrends Verified is widely considered one of the most respected performance benchmarks in the real estate industry.
Each year, RealTrends verifies sales production data to identify the highest-performing real estate professionals and teams across the country. Inclusion in the rankings means a team is among the top 1.5% of agents and teams nationwide based on measurable results.
For consumers, this provides an objective way to evaluate experience, consistency, and market performance when selecting a real estate advisor.
A Top 1% Real Estate Team in Chicago, Chicagoland, and Nationwide
While the RealTrends ranking recognizes the top 1.5% of professionals nationwide, Busby Group's performance consistently places us among the top 1% of real estate teams in Chicago, throughout Chicagoland, and nationally.
Over the years, we have built our business around a simple philosophy: combine expert market knowledge, strategic guidance, and concierge-level service to help clients make confident real estate decisions.
Today, that approach has resulted in:
More than $1 billion in career sales
Nearly 90% referral-based business
Recognition among the top-performing teams locally and nationally
Trusted relationships with buyers, sellers, investors, developers, attorneys, financial advisors, healthcare professionals, and corporate leaders
What This Recognition Means for Our Clients
Awards and rankings are meaningful, but what matters most is the impact they have on the people we serve.
In 2025 alone, Busby Group helped more than 100 buyers, sellers, investors, and relocating families successfully navigate the Chicago real estate market.
Whether helping a homeowner maximize value, coordinating a complex sell-to-buy move, securing an off-market opportunity, or managing a luxury relocation, our goal remains the same: deliver exceptional results while making the process as seamless as possible.
Why Clients Choose Busby Group
Concierge-Level Service
Our dedicated in-house concierge team helps coordinate every aspect of the process, from vendors and repairs to movers, organizers, attorneys, contractors, and trusted local resources.
Sell-to-Buy Expertise
Many homeowners need to sell before purchasing their next property. We specialize in helping clients align both sides of the transaction to maximize flexibility, certainty, and financial outcomes.
Access to Off-Market Opportunities
A significant number of transactions occur through private networks before reaching the public market. Our relationships throughout Chicago and across the country help create unique opportunities for both buyers and sellers.
Hyper-Local Market Expertise
From Lincoln Park, Gold Coast, River North, West Loop, Bucktown, and Logan Square to the North Shore, Western Suburbs, and Southwest Suburbs, our team provides neighborhood-specific expertise backed by decades of experience.
Thank You to Our Clients, Team, and Partners
This recognition would not be possible without the trust of our clients, the support of our referral partners, and the commitment of our incredible team.
We are especially grateful to the clients who continue to introduce us to their friends, family members, colleagues, and neighbors. The fact that nearly 90% of our business comes from referrals is one of the accomplishments we are most proud of.
We are also thankful for our partnership with Compass and the resources, technology, and collaborative network that help us deliver exceptional service across Chicago and beyond.
Looking Ahead
As we continue through 2026, our focus remains unchanged.
We will continue to provide:
Strategic real estate guidance
Data-driven market expertise
Concierge-level support
Strong negotiation and advocacy
Exceptional client experiences
Whether you're buying, selling, investing, relocating, or simply exploring your options, we're always happy to serve as a resource.
About Busby Group
Busby Group is a top 1% real estate team serving Chicago and the surrounding suburbs. With more than $1 billion in career sales, nationally recognized performance, and a dedicated in-house concierge department, we help clients navigate every stage of the real estate process with confidence, clarity, and results.
Helping a Retired Professional Athlete Build Long-Term Wealth
A retired Seattle Seahawks player was referred to us while exploring investment opportunities in Chicago. Living out of state, he wanted properties with strong financial returns that required minimal maintenance.
We analyzed cap rates, gross rent multipliers (GRM), projected cash flow, and long-term appreciation before identifying several investment opportunities that aligned with his goals. Over time, we helped him purchase multiple properties and expand his portfolio.
Rather than hiring a property manager, he relied on our trusted network of local contractors and vendors. Today, we continue serving as a local resource, helping simplify out-of-state ownership.
Highlights:
Investment property analysis
Multiple acquisitions
Vendor network for self-management
Long-term investment guidance
Finding the Right Home on a Tight NFL Timeline
When a Chicago Bears player was traded to the team, his agent contacted us with an urgent need for housing near the team's practice facility. Luxury short-term rentals in the area were limited, and the family also needed flexibility should another trade occur.
We located the ideal property and negotiated an early termination clause, giving the family peace of mind if plans changed. To make the transition effortless, we coordinated a fully furnished home complete with furniture, televisions, linens, kitchenware, and household essentials before they arrived.
By handling every detail, we allowed the player to focus on football while his family settled comfortably into their new home.
Highlights:
Luxury rental secured on a tight timeline
Flexible lease negotiated
Fully furnished move-in ready home
Concierge relocation services
Built on Trust and Shared Values
PROVEN PARTNERSHIPS
Jennifer Guimond-Quigley, Attorney At Law
Some professional relationships grow from shared values long before business is ever involved.
Our relationship with Jennifer Guimond-Quigley began more than a decade ago through the Neighborhood Parents Network, where Jennifer served as president. Through our mutual involvement in supporting Chicago families and communities, a trusted professional relationship naturally developed over the years.
Since then, we have collaborated closely on a variety of client matters, particularly those involving estate-related transitions and the sale of homes following the loss of a loved one.
Jennifer has become a valued resource for many of our clients, while she has trusted Busby Group to support families navigating highly emotional transitions that require patience, discretion, and thoughtful communication.
Our shared approach centers around professionalism, responsiveness, organization, and genuine care for the people involved.
“Julie and her team have been amazing to work with. Our initial introduction was through Neighborhood Parents Network, a Chicago-based nonprofit that provides resources to parents, which is something Julie and I have both been passionate about. We have successfully collaborated on real estate matters with Julie and her team over the years and notably, I have been comfortable sending clients to The Busby Group who are selling property after the death of a loved one, which is an exceptionally delicate and emotional time and requires special care. They handle all of it with skill and ease. I am thrilled to have them in my corner as a trusted resource and will continue to rely on them when the need arises.”
- Jennifer
Built on Trust and Shared Values
Transitions involving estate planning, probate, or inherited property often require coordination between multiple trusted professionals.
We are grateful for partnerships with attorneys like Jennifer who share our belief that clients deserve not only expertise, but also compassion, communication, and thoughtful guidance during important life moments.
Lock-and-Leave Living in Chicago
Two Luxury Residences Designed for Convenience, Security, and Effortless City Living
For many buyers today, especially those balancing multiple homes, frequent travel, or seasonal living between Chicago and warmer climates like Florida or Arizona, convenience matters just as much as the home itself.
That is why “lock-and-leave” living continues to be one of the most desirable lifestyle trends in Chicago luxury real estate.
The ideal lock-and-leave home offers more than beautiful finishes. Buyers are often looking for:
Full-service buildings with door staff and secure access
Minimal maintenance and simplified ownership
Strong amenity offerings
Walkability to dining, parks, culture, and the lakefront
Easy connectivity for those splitting time between cities
We are also seeing increased demand from seasonal residents and “snowbirds” who want to enjoy Chicago during its best months while maintaining the flexibility to spend winters in destinations like Naples, Scottsdale, Palm Beach, or Arizona.
Two current Busby Group listings embody this lifestyle particularly well.
211 N Harbor Dr #1801
Elevated Living at Cirrus in Lakeshore East
Set within the highly sought-after Cirrus building in Lakeshore East, this residence offers a refined and highly service-oriented living experience.
The home itself features sweeping views of Lake Michigan, Lakeshore East Park, and the skyline, paired with thoughtful upgrades including custom closets, designer lighting, and custom window treatments.
But what truly makes this property ideal for lock-and-leave living is the building itself.
Residents enjoy:
24-hour door staff and secure entry
Professional on-site management
Indoor and outdoor pools
Extensive fitness and wellness amenities
Co-working spaces and entertaining lounges
Golf and sports simulators
Easy access to the lakefront, Riverwalk, dining, and downtown
This type of full-service environment allows owners to enjoy the city when they are here while maintaining peace of mind when away.
View property here:
211 N Harbor Dr #1801
1250 S Michigan Ave #2802
Full-Service South Loop Living with Skyline and Lake Views
Located in the heart of the South Loop, Michigan Avenue Tower I offers another excellent example of lock-and-leave luxury.
This high-floor residence combines expansive views with the convenience of full-service condo living in one of Chicago’s most connected neighborhoods.
Buyers are drawn to this location because of its:
Close proximity to Grant Park and the lakefront
Walkability to museums, restaurants, and downtown offices
Strong building amenities and security
Easy access to city conveniences without the maintenance of a larger home
The building features:
24-hour door staff
Fitness center
Outdoor pool and sundeck
Secure entry and professional management
For buyers spending part of the year elsewhere, this creates an ideal setup that blends flexibility, security, and convenience with an elevated city lifestyle.
View property here:
1250 S Michigan Ave #2802
Why Lock-and-Leave Living Continues to Grow
We continue to see strong demand for homes that support flexibility and ease of ownership.
Many buyers today are:
Splitting time between Chicago and warmer climates
Purchasing second or third residences
Downsizing from larger suburban homes
Looking for a lower-maintenance lifestyle
Wanting full-service amenities and security
Chicago’s luxury condo market offers a unique opportunity to combine:
Full-service living
Prime urban access
Lakefront lifestyle
Relative value compared to coastal cities
For many buyers, it creates the perfect balance between convenience, lifestyle, and long-term flexibility.
Busby Group Perspective
As more buyers prioritize flexibility and lifestyle-driven living, full-service luxury buildings with strong amenities, security, and connectivity continue to stand out.
With over $1B in career sales and extensive experience helping clients navigate second homes, relocations, and seasonal living, we help buyers identify not just the right property, but the right lifestyle fit as well.
Shared Clients and Strategy
PROVEN PARTNERSHIPS
Natalie Hatfield, Estate Planning Attorney
Some of the strongest professional relationships are built through shared clients and shared values.
Our relationship with estate planning attorney Natalie Hatfield began after one of her clients suggested that our teams should work together, recognizing how aligned our approaches were in terms of organization, communication, professionalism, and genuine care for clients navigating important life transitions.
Since then, we have worked together on estate-related transactions requiring thoughtful coordination, strategic preparation, and a high level of responsiveness.
Natalie and her team bring clarity and structure to the legal side of estate planning and administration, while Busby Group helps guide clients through the real estate portion with hands-on coordination and concierge-level support. Together, the goal is to create a more seamless and supportive experience for families during what can often be overwhelming situations.
One estate sale in particular required an accelerated timeline involving home preparation, strategic updates, staging, launch strategy, and closing coordination. Working collaboratively, our teams helped create a smooth process and a strong outcome for the estate.
“I was referred to Julie Busby and her team by my brother and sister-in-law. They had worked with the Busby Group to sell their Chicago home and had a good experience. I needed to quickly sell a home for an Estate I was working on. Julie and her team responded to me on the very same day I reached out to them. Every single step of the way Julie and her team were above and beyond professional, efficient, and pleasant. I was amazed at the work they did in accomplishing a home remodel, listing, and sale within 30 days of my initial call. Their good work resulted in 13 different offers all over asking price and a quick expeditious closing. I cannot say enough good things about the Busby Group.” – Natalie
Why Partnerships Matter
Estate and transition-related sales often involve multiple professionals working together on behalf of a client or family.
We value partnerships with attorneys, financial advisors, insurance professionals, and senior living experts who share our belief that communication, organization, and empathy matter just as much as the transaction itself.
Helping a Professional Athlete's Family Feel at Home
When the wife of a Chicago Cubs player contacted us through our Sports Star Relocation Network, the family needed to relocate quickly following a trade. With young children, they wanted more than just a rental. They wanted a place that felt safe, comfortable, and ready to call home.
Within days, we secured the right property, negotiated favorable lease terms, recommended the best neighborhood for their lifestyle, and ensured the home was properly furnished before they arrived.
We remained their concierge throughout their time in Chicago, helping with vendors, recommendations, and day-to-day needs. When another trade came, we coordinated their transition out of Chicago just as seamlessly as their arrival. Today, we remain in touch and are grateful for the lasting friendship that grew from the experience.
Highlights:
Quick relocation after a trade
Family-focused neighborhood guidance
Concierge service throughout their stay
Lasting client relationship
A Neutral and Steady Approach During a Difficult Divorce
LEGACY & TRANSITIONS SUCCESS STORY
This sale involved a particularly challenging divorce situation where maintaining professionalism, neutrality, and clear communication was essential throughout the process.
Both attorneys appreciated our calm and balanced approach, recognizing the importance of having a real estate team that could remain objective while helping move the transaction forward constructively.
At the time, the property was located in an area facing softer buyer demand, making thoughtful preparation and positioning especially important to achieving a successful outcome.
After evaluating the market and the home’s condition, we implemented strategic, cost-conscious updates designed to improve presentation and maximize appeal without creating unnecessary expense. Through our trusted vendor network, we coordinated improvements and staging that helped buyers better connect with the home and envision its potential.
Throughout the process, our role extended beyond simply marketing the property. We focused on maintaining structure, reducing friction where possible, and helping all parties navigate the transaction with greater clarity and professionalism.
The result was a successful sale that allowed both parties to move forward and close an important chapter.