Best Weekend Getaways from Chicago

As a local, living in The Windy City is the best, but heading out for the city for a rejuvenating weekend is part of the self-care regiment here. I love how within just a short drive, I can swap skyscrapers for shorelines and scenic trails to slow down in a place made for reconnecting.

I've always thought that choosing where to stay adds to the magic, whether it’s a rustic cabin in the woods, or a full service spa resort by the lake. Here are some of the most unique Chicago-area escapes we love and I hope you’ll try for your next 48 hour weekend getaway from Chicago.

1. Grand Geneva Resort - 1 hour 30 minutes from Chicago

I had such a joyful stay at this resort, and from the moment we arrived, I could feel how much care went into creating a warm and welcoming atmosphere.

I loved that the property sat on 1,300 acres of rolling hills (and golf courses!), and I felt instantly transported into a peaceful retreat where I could truly unwind.

My room for two days 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 60-minute massage and time in the steam room, my personal highlight.

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, we explored the resort’s walking trails, took a dip in the pool, and even tried out the fitness center, which I thought was super well equipped!

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.

Check prices at Grand Geneva Resort and Spa

What I loved best:

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

2. The Abbey Resort - 1 hour 40 minutes

I felt such a magical welcome the moment I entered this iconic A-frame lobby with its warm fireplace and vintage nautical touches that completely won me over.

The Abbey Resort is actually just 15 minutes from Grand Geneva Resort and Spa which is super convenient if you want to stay in two different places. Once again, 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 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 for two easy days on our weekend getaway, complete with plush bedding, a private balcony, and cottage-inspired decor that felt super cozy.

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.

Chris, my son and 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 where I had a filling steak, and my husband went for seafood, all with amazing harbor views! In addition, Waterfront restaurant offered a different ambiance with its laid-back bites and refreshing cocktails.

We discovered endless fun with activities like the indoor arcade for my son, a movie theater for our family to enjoy together, ice skating (depending on the season!), and nightly live music...all adding an exciting energy.

I appreciated how the resort offered thoughtful family-friendly amenities that made it feel welcoming to every age of traveler.

Check prices at The Abbey Resort

What I loved best:

Relaxing on the balcony with a cup of coffee in the morning was my personal highlight, so simple but it really offered the weekend reset I was craving.

3. Grand Traverse Resort - 5 hours from Chicago

There’s a quiet magic to northern Michigan, and this resort captures it well. 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 for our long 3-day weekend had floor-to-ceiling windows with sweeping views of Grand Traverse Bay, and it quickly became my favorite spot to watch the sunrise with coffee in hand.

We spent the entire long weekend exploring the resort’s sprawling property, had fun for hours in the indoor pool complex with water slides (my son's favorite!), and checked out the private beach club on Lake Michigan which was such a treat in the middle of hot July summer (my favorite!)

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.

We had a family dinner at Aerie, the signature restaurant that received the Wine Spectator Award of Excellence, and enjoyed fresh local cuisine with panoramic views.

Check prices at Grand Traverse Resort and Spa

What I loved best:

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.

A downside? Some activities are only seasonal. In addition, since this resort is 5 hours from Chicago, I think it works best as a 3-day weekend, so either take off work on Friday or on Monday for the most relaxing time.

4. The Knickerbocker on the Lake, Milwaukee - 1 hour 30 minute from Chicago

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

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.

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

I loved how my suite for two days combined vintage character with modern comfort—hardwood floors, high ceilings, and classic décor blended beautifully with updated amenities. 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.

Since Milwaukee offers so many things to do, we were never bored and wished for a longer stay. Activities and attractions included museums like the Milwaukee Art Museum and Harley-Davidson Museum, outdoor activities at Bradford Beach and the Lakefront Trail, historic sites such as the Pabst Mansion, and food and drink experiences at the Milwaukee Public Market and various breweries. We were traveling with our son so we spent the first morning at the Milwaukee County Zoo and later that afternoon strolling through the Mitchell Park Domes.

After a day exploring, I found the attached restaurant and bar at The Knickerbocker on the Lake, Milwaukee to be convenient and cozy, offering hearty meals and cocktails that made for the coolest way to end our evenings.

Check prices at The Knickerbocker on the Lake

What I loved best:

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

5. Sweethaven Resort - 1 hour 20 minutes from Chicago

I felt so relaxed the moment I arrived at this place, tucked away in the woods just minutes from Lake Michigan...it was such a peaceful escape into nature, yet very close to the city.

I loved that the resort offered charming cottages and cabins, each with cozy décor, fireplaces, and plenty of space to unwind.

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.

Union Pier carried that mix of cottage charm and natural calm. The resort itself felt cozy, a cluster of cabins hidden among the trees. We stayed in The Dove cottage (in the picture) for two care-free days which has a queen-size bed, a queen sleeper sofa, a romantic fireplace, screened porch with a Hot Tub, and a private deck with a Weber grill.

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.

What I loved best:

My favorite part was sipping coffee on the porch in the early morning quiet.

We also appreciated the little touches, like hammocks tucked between trees, fire pits stocked with wood, and friendly staff who made the whole experience welcoming.

A downside? You have to call to make a reservation because they don't offer online bookings.

6. Amway Grand Plaza, Grand Rapids - 2 hours 45 minutes from Chicago

We absolutely adore how this hotel blends historic charm with modern luxury—it’s like stepping into a dreamy castle right in the heart of Grand Rapids.

Nestled next to the DeVos Place Convention Center and connected via skywalk to the Van Andel Arena, our stay felt super convenient for both events and exploration in downtown Grand Rapids.

We were wowed by the lobby’s stunning details, including sparkling chandeliers, a stone fountain, and the largest gold-leaf ceiling in North America (such a hidden gem of elegance!).

Our room for two days in the glass tower offered spectacular river or city views and came with plush bedding, 50-inch flat screens, high-speed Wi-Fi, and luxe bath products—a perfect haven of comfort.

We loved indulging in the variety of on-site dining options—everything from hearty steaks at Ruth’s Chris to modern Spanish bites at MDRD and global comfort fare at Wolfgang Puck’s Kitchen—so many delicious choices without even stepping outside.

The hotel’s setting felt like one of my coolest ideas—historic architecture and modern design seamlessly merged, creating an atmosphere that’s unique, romantic, and joyfully vibrant that completely won me over.

What I loved best:

7. The Newport Resort - 4 hours 30 minutes

I felt an instant sense of comfort when I checked into this resort, with its cozy atmosphere and welcoming staff who made me feel right at home. The views alone made me feel like I’d stepped into a place built for slowing down and it instantly became one of my best weekend getaways from Chicago.

I loved that our suite for three easy weekend nights came with a full kitchen, a spacious living area, and private balcony, and 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, and I could smell fresh pine and hear the faint hum of boats heading back to the marina.

I appreciated all the resort extras like the indoor pool, outdoor pool in warm weather, fitness center, game room, and daily breakfast, which made my stay even more enjoyable.

Check prices at The Newport Resort

What I loved best:

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 think that The Newport Resort is one of the best weekend getaways from Chicago. Why? First of all, you'll be at the doorstep to the Door County highlights like vineyards, state parks, and hidden beaches. Secondly, I loved that I could return to the resort’s calm, cool vibe after a busy day of adventuring.

Hi, I'm Ema. I'm the face behind VacationIdea.com. My husband, son are frequent travelers and spent 5 years on the road discovering some of the best places to visit in the USA. We base ourselves in a new place every 4 weeks weeks which has allowed us to experience each destination as a local. I love to chase unique things to do near me and revisit old favorites for a cool, fresh perspective. I'm also eager to learn from my fellow travelers to see what works for people and what doesn't. Whether you like great sunsets, hidden gems, places of mystery, famous attractions, or underrated experiences, here you'll find all of those recommendations from locals that won me over. Let's explore together! More about us.

 

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