Sometimes the best way to love a city like Chicago is to step away from it for a little while. A weekend escape doesn’t have to mean far-flung travel—it can be as simple as crossing state lines, chasing a lake breeze, or curling up by a fire in a place that feels worlds away. Each of these getaways offered me something different: rest, play, reflection. I remember thinking, “There’s more room to breathe when the skyline’s in the rearview.” And that space? It has a way of bringing clarity you didn’t know you were missing.
Best Weekend Getaways from Chicago
For families with kids: Grand Geneva Resort - 1 hour 30 minutes from Chicago
Just a short drive from the city,
Grand Geneva Resort and Spa felt like stepping into a different rhythm—where the air was calmer and the days stretched out longer. The resort had a way of wrapping you in comfort without trying too hard. Whether I was walking the wooded trails or watching golfers move across the green, everything felt easy. I remember thinking, “This is what my shoulders feel like when they finally drop.”
What I Loved Most: Sipping coffee by the fireplace in the lobby, and soaking in the outdoor hot tub while snowflakes melted on my skin.
My highlights? Dinner at Ristorante Brissago. I ordered the housemade butternut squash ravioli with sage brown butter—it was delicate and rich, like the whole weekend. I watched the sky turn deep blue through tall windows, the kind of dinner that asks nothing of you but presence.
Grand Geneva Resort and Spa At a Glance
- Drive Time from Chicago: ~1.5 hours northwest
- Vibe: Relaxed, upscale, woodsy
- Highlights: Spa, golf, skiing, trails, indoor pool
- Best Time to Visit: Winter for coziness or fall for foliage
- Cost: Moderate to high
- Hours: Resort check-in 4pm, spa 9am–6pm
- Address: 7036 Grand Geneva Way, Lake Geneva, WI
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 felt peaceful yet full of possibility. I walked the beach in the early morning light and felt something shift. I remember thinking, “It’s amazing how far away you can feel in just one weekend.”
What I Loved Most: Watching the sun rise over Grand Traverse Bay and lingering in the spa steam room long after my treatment ended.
My highlights? Brunch at Aerie Restaurant & Lounge. I had the smoked whitefish Benedict with lemon hollandaise and a side of roasted potatoes—elegant and satisfying. Sitting at the window with sweeping lake views, the city felt beautifully distant.
Grand Traverse Resort and Spa At a Glance
- Drive Time from Chicago: ~5.5 hours north
- Vibe: Serene, polished, lakeside luxury
- Highlights: Spa, golf, private beach access, indoor pool
- Best Time to Visit: Summer and early fall
- Cost: Moderate to high
- Hours: Check-in 4pm, dining varies by season
- Address: 100 Grand Traverse Village Blvd, Acme, MI
For a lakeside retreat: The Abbey Resort - 1 hour 40 minutes
The Abbey Resort brought a kind of lakefront calm I didn’t realize I needed. Boats bobbed in the harbor, and the crisp air off Geneva Lake carried a sweetness that slowed my breath. I wandered the property with no plans, and that felt like the real luxury. I remember thinking, “Maybe peace is just about giving yourself permission to do less.”
What I Loved Most: Watching the sunset from the dock with my feet dangling over the edge and a glass of wine in hand.
My highlights? Dinner at 240° West. I had the grilled lake perch with lemon caper butter and seasonal vegetables—it was simple, fresh, and perfectly unhurried. The whole meal mirrored the pace of the weekend.
The Abbey Resort At a Glance
- Drive Time from Chicago: ~1.5 hours northwest
- Vibe: Nautical, peaceful, charming
- Highlights: Spa, indoor pool, lakeside fire pits
- Best Time to Visit: Spring through fall
- Cost: Mid-range
- Hours: Spa 9am–7pm, check-in 4pm
- Address: 269 Fontana Blvd, Fontana-on-Geneva Lake, WI
For a beach holiday: The Newport Resort - 4 hours 30 minutes
a href="https://expedia.com/affiliate/lcPLJGB" target="_blank">Newport Resort felt like one of those places that gives you permission to pause. The suites were cozy and quiet, with balconies that overlooked trees instead of traffic. I spent hours reading, soaking in the tub, and listening to nothing but the wind. I remember thinking, “This is the kind of silence that feels like healing.”
What I Loved Most: Morning coffee on the balcony wrapped in a blanket, watching the fog lift from the trees.
My highlights? A warm, comforting dinner at Wild Tomato just down the road. I had the Sausage & Shroom pizza with garlic cream sauce and a Door County cherry soda—indulgent, local, and full of flavor.
The Newport Resort At a Glance
- Drive Time from Chicago: ~4.5 hours north
- Vibe: Quiet, intimate, nature-focused
- Highlights: Fireplace suites, indoor pool, walkable to restaurants
- Best Time to Visit: Fall for foliage, winter for seclusion
- Cost: Affordable to mid-range
- Hours: Check-in 3pm, check-out 11am
- Address: 7888 Church St, Egg Harbor, WI
For an affordable Milwaukee getaway: The Knickerbocker on the Lake - 1 hour 30 minute
Right in the heart of Milwaukee, The Knickerbocker on the Lake had an old-world elegance that felt both timeless and intimate. The historic charm showed in the crown moldings, the quiet hallways, and the view of the lake from my window. I remember thinking, “This is city living with soul.”
What I Loved Most: Walking along the lakefront path at sunrise, city skyline behind me, and the quiet water ahead.
My highlights? Breakfast at The Knick Restaurant, right on site. I had the crab cake Benedict with dill hollandaise, and it was as rich and layered as the building itself.
The Knickerbocker on the Lake At a Glance
- Drive Time from Chicago: ~1.5 hours north
- Vibe: Vintage, elegant, urban
- Highlights: Lakefront access, on-site dining, walkable to Milwaukee museums
- Best Time to Visit: Year-round
- Cost: Moderate
- Hours: Restaurant 8am–9pm, hotel check-in 3pm
- Address: 1028 E Juneau Ave, Milwaukee, WI
Sweethaven Resort - 1 hour 20 minutes from Chicago
Sweethaven felt like visiting a friend’s secret cabin in the woods—charming, warm, and delightfully unplugged. The cottages were nestled under tall trees, with hammocks and fire pits that begged you to linger. I remember thinking, “This might be the coziest place I’ve ever been.”
What I Loved Most: Reading in a screened-in porch during a rainstorm, wrapped in a soft blanket with no plans at all.
My highlights? Dinner at Timothy’s Restaurant just minutes away. I had the maple-glazed salmon with whipped sweet potatoes and a local IPA—it was hearty and comforting, just like the weekend.
Sweethaven Resort At a Glance
- Drive Time from Chicago: ~1.5 hours east
- Vibe: Cozy, woodsy, unplugged
- Highlights: Private cottages, fire pits, pet-friendly, walk to beach
- Best Time to Visit: Late spring through fall
- Cost: Budget to mid-range
- Hours: Check-in 3pm, check-out 11am
- Address: 9517 Union Pier Rd, Union Pier, MI
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.