Weekend Getaways from Chicago

I’ve discovered that weekend getaways from Chicago are a wonderful mix of lakeside calm, forests painted by the seasons, and charming small towns—perfect escapes when you want both adventure and coziness. Within just a few hours, you can swap skyscrapers for shorelines, boutique inns, or scenic trails, and slow down in a place made for reconnecting.

Choosing where to stay adds to the magic, whether it’s a rustic cabin in the woods, a spa resort by the lake, or a boutique hotel in a quaint downtown. Here are some of the most unique Chicago-area escapes I came across that I think you’ll love for your next weekend adventure.

1. For families with kids: Grand Geneva Resort - 1 hour 30 minutes from Chicago

We drove about an hour and a half northwest from Chicago, farmland giving way to rolling Wisconsin hills. Lake Geneva shimmered in the distance, and soon the Grand Geneva Resort and Spa appeared, set on 1,300 acres of green lawns, golf courses, and wooded trails.

I had such a joyful stay at Grand Geneva Resort and Spa, and from the moment I arrived, I could feel how much care went into creating a warm and welcoming atmosphere.

I loved that the property sat on hundreds of acres of rolling hills, and I felt instantly transported into a peaceful retreat where I could truly unwind.

My room was spacious and inviting, with plush bedding, a cozy sitting area, and a balcony that looked out over the golf course and lake—my favorite view to wake up to.

I spent a full afternoon at the spa, where I enjoyed a relaxing massage and time in the steam room, and it was one of the most rejuvenating experiences I’ve had in a long time.

Dining on-site was also a highlight for me—I loved starting my mornings with fresh coffee and a hearty breakfast, then ending my evenings with a glass of wine at the rustic lodge-style restaurant.

During the day, I explored the resort’s walking trails, took a dip in the pool, and even tried out the fitness center, which was far more equipped than I expected.

I also appreciated how family-friendly the resort was, with activities for kids, while still offering plenty of quiet spaces for adults looking for a more romantic atmosphere.

One of the coolest parts of my stay was taking the trolley ride into nearby Lake Geneva—it made exploring the area effortless and fun.

For me, Grand Geneva Resort and Spa was not just a hotel, but a destination full of relaxation, recreation, and charm all in one.

Check prices at Grand Geneva Resort and Spa

2. For a lakeside retreat: The Abbey Resort - 1 hour 40 minutes

On the second night, we checked into The Abbey Resort, just 15 minutes from Grand Geneva Resort and Spa. I wanted to soak in lakeside views, enjoy the resort’s amenities, take a walk along the lake path, and discover a memorable dinner nearby.

I felt such a magical welcome the moment I entered the iconic A-frame lobby with its warm fireplace and vintage nautical touches.

I could tell this was a cool place from its serene lakeside setting—not overly crowded but just right on the shore of Geneva Lake.

I relaxed instantly in my lakeside-style guest room, complete with plush bedding, a private balcony, and cottage-inspired decor that felt both cozy and inviting.

I indulged in the 35,000 sq ft Avani Spa where I enjoyed a steam room, salt room, and a rejuvenating massage—pure relaxation that wasn’t just about pampering, but restoring my spirit.

I spent afternoons exploring the resort’s 90 acres of beautifully manicured grounds, watching boats drift in the marina, and savoring fireside s’mores as dusk settled over the water.

I savored meals at two on-site restaurants—240° West with its steaks, seafood, and harbor views, and Waterfront for its laid-back bites and refreshing cocktails—and they were absolutely my favorite dining experiences of the stay.

I discovered endless fun with activities like the indoor arcade, movie theater, seasonal ice skating, and nightly live music—all adding an exciting energy without ever feeling over the top.

I appreciated how the resort offered a perfect romantic escape for me, while also having thoughtful family-friendly amenities that made it feel welcoming to every kind of traveler.

I left feeling like I had found a brilliant idea for a lakeside getaway that truly balances tranquility and vibrant fun.

Check prices at The Abbey Resort

3. For golfers: Grand Traverse Resort - 5 hours from Chicago

There’s a quiet magic to northern Michigan, and Grand Traverse Resort and Spa captures it well. Tucked near the shores of Lake Michigan, the resort was peaceful yet full of possibility.

I felt an immediate sense of excitement as I arrived at Grand Traverse Resort, with its striking glass tower rising above the trees and Lake Michigan nearby.

I loved that my room had floor-to-ceiling windows with sweeping views of Grand Traverse Bay—it quickly became my favorite spot to watch the sunrise with coffee in hand.

I spent hours exploring the resort’s sprawling property, from the indoor pool complex with water slides to the private beach club, which made my stay feel like a true getaway.

I treated myself to a rejuvenating massage at the spa, and I left feeling completely refreshed—it was such a magical experience of calm and renewal.

I also found the resort’s golf courses to be incredible, especially The Bear, which challenged me with its design while surrounding me with stunning natural scenery.

I dined at Aerie, the signature restaurant perched high above the resort, and enjoyed fresh local cuisine with panoramic views—it was the coolest dining atmosphere I’ve experienced in a long time.

I liked that there were plenty of family-friendly activities, yet the resort also felt romantic and peaceful, offering the best of both worlds depending on what I wanted that day.

I shopped at the gallery of boutiques inside the resort, picking up unique local gifts and treats to bring home, which added a joyful touch to my trip.

I left feeling like Grand Traverse Resort wasn’t just a stay—it was a destination filled with variety, comfort, and memorable moments I can’t wait to relive.

Check prices at Grand Traverse Resort and Spa

4. For an affordable Milwaukee getaway: The Knickerbocker on the Lake - 1 hour 30 minute

We flew directly from Austin to Milwaukee, a quick under-three-hour trip, rented a car, and then drove less than 20 minutes into the heart of the city. By the time we reached The Knickerbocker on the Lake, the historic brick façade already felt like a gateway into another era.

I was looking forward to walking along Lake Michigan, visiting the art museum, and finishing the day with a good meal downtown.

I felt immediately charmed when I arrived at The Knickerbocker on the Lake, with its historic façade and warm, welcoming vibe that made me feel like I was stepping into a piece of Milwaukee’s past.

I loved how my suite combined vintage character with modern comfort—hardwood floors, high ceilings, and classic décor blended beautifully with updated amenities, and my favorite part was the kitchenette that made it easy to feel at home.

I spent time in the on-site spa, where I treated myself to a relaxing massage, and I left feeling refreshed and cared for—it was a magical escape without ever leaving the hotel.

I liked that the location put me right near the lakefront, so I could enjoy morning walks along Lake Michigan and still be close to downtown’s restaurants, shops, and entertainment.

I found the attached restaurant and bar to be convenient and cozy, offering hearty meals and cocktails that made for the coolest way to end my evenings.

I also appreciated the building’s historic charm, with architectural details and a sense of heritage that gave the whole place a unique personality.

I enjoyed that it was equally perfect for a romantic getaway or a quiet solo retreat, with just the right balance of intimacy and comfort.

I left feeling like The Knickerbocker on the Lake gave me a brilliant idea for a stay that’s both classic and comfortable—truly a gem in Milwaukee.

Check prices at The Knickerbocker on the Lake

5. Sweethaven Resort - 1 hour 20 minutes from Chicago

We drove up from Chicago in just under 90 minutes, tracing the curve of Lake Michigan until the bustle of the city gave way to quiet dunes and shaded roads. By the time we reached Union Pier, the slower rhythm of this lake town had already set in, and checking into Sweethaven Resort was like stepping into a tucked-away retreat.

I wanted to walk along the sandy shoreline, spend time in the resort’s wooded setting, enjoy a relaxed meal nearby, and let the evening close with a sunset over the lake.

Union Pier carried that mix of cottage charm and natural calm. The air smelled of pine and bonfires, and I could hear the lake’s steady hush in the distance. The resort itself felt cozy, a cluster of cabins hidden among the trees.

I felt so relaxed the moment I arrived at Sweethaven Resort, tucked away in the woods just minutes from Lake Michigan—it felt like a peaceful escape into nature.

I loved that the resort offered charming cottages and cabins, each with cozy décor, fireplaces, and plenty of space to unwind, and my favorite part was sipping coffee on the porch in the early morning quiet.

I spent my afternoons walking the wooded trails, riding bikes into the nearby beach towns, and then returning to the resort to enjoy campfires under the stars—it was such a magical way to end the day.

I liked how family-friendly the resort was, with playgrounds, open lawns, and activities for kids, yet it still felt private enough to work perfectly as a romantic getaway.

I cooked meals in the fully equipped kitchen of my cabin, but I also enjoyed exploring nearby restaurants and breweries, which made the stay feel both homey and adventurous.

I found the location to be ideal—close to the beaches of Lake Michigan, the shops of Union Pier and New Buffalo, and wineries that made the coolest day trips.

I enjoyed the little touches too, like hammocks tucked between trees, fire pits stocked with wood, and friendly staff who made the whole experience welcoming.

I left feeling like Sweethaven Resort was a brilliant idea for anyone wanting a true Midwest retreat—a mix of comfort, nature, and joyful memories waiting to be made.

6. For a beach holiday: The Newport Resort - 4 hours 30 minutes

We drove north from Milwaukee, about 3 hours up into Door County, where farmland slowly gave way to shoreline towns. By the time we reached Egg Harbor and pulled into The Newport Resort, the small village charm and the wide sweep of Green Bay made me feel like I’d stepped into a place built for slowing down.

I wanted to explore local shops, spend some time at the resort’s pool and trails, and end the evening watching the sun melt into the bay.

Egg Harbor felt playful and relaxed, with colorful storefronts and friendly cafés balanced against the quiet of the water. From the resort’s balconies, I could smell fresh pine and hear the faint hum of boats heading back to the marina.

I felt an instant sense of comfort when I checked into The Newport Resort, with its cozy atmosphere and welcoming staff who made me feel right at home.

I loved that every suite came with a full kitchen, spacious living area, and private balcony—it was my favorite setup because I could cook, relax, and still enjoy resort-style amenities.

I spent my mornings sipping coffee on the balcony while looking out over the trees, then heading out to explore Egg Harbor’s charming shops and waterfront, which were just a short walk away.

I enjoyed afternoons by the indoor pool, and when the weather was warm, the outdoor pool area became a magical spot to lounge in the sun.

I liked how family-friendly the resort felt, with playgrounds, bike rentals, and plenty of space for kids to run, yet it also had quiet corners that worked perfectly for a romantic getaway.

I appreciated the little extras like the fitness center, game room, and daily breakfast, which made my stay both easy and enjoyable.

I explored nearby Door County highlights—vineyards, state parks, and hidden beaches—and loved that I could return to the resort’s calm, cool vibe after a busy day of adventuring.

I ended each evening by unwinding in the whirlpool tub back in my suite, feeling grateful for such a relaxing end to the day.

I left knowing The Newport Resort was a brilliant idea for a trip to Door County—combining convenience, comfort, and a joyful sense of escape.

Check prices at The Newport Resort

Conclusion

By the time I returned to Chicago, something in me had shifted. I wasn’t just rested, I was reminded of how much beauty there is just beyond the familiar. Whether it was a quiet lakeside morning or a glass of wine by a fireplace, these places brought me back to myself. And honestly, that’s what the best weekends do. They don’t just take you somewhere new, they help you return home a little softer, a little clearer, a little more you.

Hi, I'm Ema. Ready to plan your next weekend getaway? Let me help. I have 30 years of experience, over 400,000 social media followers, and my work as a travel expert has been mentioned on abc6 Morning Show, Best of the Web, USAToday, and many other outlets. When I'm not traveling around the USA, I live in Austin, TX with my husband and son. Click for more.

 

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