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 or road trip 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, Illinois.
Grand Geneva Resort - 1 hour 30 minutes from Chicago
This is one of my favorite weekend escapes from Chicago because it delivers a little bit of everything without any stress. There are heaps of unique things to do here! Chris and I both absolutely love Grand Geneva Resort, and have been many times.
I loved that the property sat on 1,300 acres of rolling hills (and golf courses!). I felt instantly transported into a peaceful retreat where I could truly unwind on our weekend.
My room for two days was spacious and inviting. 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. You can start with fresh coffee and a hearty breakfast. Then end the evening with a glass of wine at the rustic lodge-style restaurant.
Be sure to explore the resort’s walking trails, take a dip in the pool, and try out the fitness center, which I thought was super well equipped!
What I loved best:
My personal highlight was taking the trolley ride into nearby Lake Geneva which made exploring the area effortless.
The Abbey Resort - 1 hour 40 minutes
Whenever I want a relaxing getaway that still offers plenty to do, this resort is one of my top getaways from Chicago, Illinois.
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 in one weekend.
Here you can also enjoy lakeside views, enjoy the resort’s amenities, and take a walk along the lake path.
Our room for the weekend had a private balcony, and cottage-inspired decor that felt super cozy. If you are a spa fan like me, you'll love the 35,000 square foot Avani Spa.
During the day, enjoy 90 acres of beautiful grounds, boats in the marina, and fireside s'mores in the evening.
Have a romantic dinner at the on-site restaurant 240° West where I had a filling steak, and my husband went for seafood, all with amazing harbor views!
Some super unique features here are the indoor arcade for my son, a movie theater, ice skating (in season!), and live music.
Grand Traverse Resort - 5 hours from Chicago
Ready for a trip that showcases Michigan’s natural beauty? There’s a quiet magic to northern Michigan as we discovered on our road trip, 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 views of Grand Traverse Bay
Your kids will love the indoor pool complex with water slides (my son's favorite!). The private beach club on Lake Michigan which was such a treat in the middle of hot July summer (my favorite!)
You can treat yourself to a rejuvenating massage at the spa.
I also found the resort’s golf courses to be incredible, especially The Bear, which challenged me with its design.
We had a family dinner at Aerie, the signature restaurant that received the Wine Spectator Award of Excellence.
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.
The Knickerbocker on the Lake, Milwaukee - 1 hour 30 minute from Chicago
Whenever I want a city getaway from Chicago that's comfortable and close to everything, this is one of my top choices. The first time we visited Milwaukee, I was genuinely surprised by how much I loved it. Sitting right on the shores of Lake Michigan, the city has a waterfront that feels more like an ocean town than a Midwestern destination. You can enjoy historic architecture, lively neighborhoods, and a cool food and brewery scene. You’ll find excellent museums, a revitalized riverwalk, professional sports, and a strong arts and music culture that gives the city a lot of personality.
One of the things I really like about Milwaukee is how easy it is to get around. Downtown is compact and walkable, and many of the main attractions are clustered close together. Bradford Beach is a popular spot in the summer, but the lakefront parks offer beautiful views year-round.
When you get hungry, there’s a great mix of comfort food and culinary creativity. The public market is a must-visit if you want to sample a little bit of everything in one place.
What I loved best:
I loved how our suite at The Knickerbocker on the Lake for two days combined vintage character with modern comfort. Details include hardwood floors, high ceilings, and classic décor. My favorite part was the kitchenette that made it easy to feel at home. I liked that the location put us right near the lakefront.
A downside? Snowstorms in the winter can cause flight delays.
Sweethaven Resort - 1 hour 20 minutes from Chicago
Set among peaceful forests and winding trails, this resort feels like one of the most relaxing hideaways near Chicago. 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.
Union Pier carried that mix of cottage charm and natural calm. The resort itself felt cozy. It's 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,and then returning to the resort to enjoy campfires under the stars.
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.
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.
Amway Grand Plaza, Grand Rapids - 2 hours 45 minutes from Chicago
When I'm in the mood for a weekend getaway from Chicago that offers both luxury and a walkable urban adventure, this place is a standout. I instantly thought our journey was worth it! We absolutely adore how Amway Grand Plaza blends historic charm with modern luxury—it’s like stepping into a dreamy castle right in the heart of Grand Rapids.
Amway Grand Plaza is next to the DeVos Place Convention Center, connected via skywalk to the Van Andel Arena.
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.
You can dine on hearty steaks at Ruth’s Chris, have modern Spanish bites at MDRD, or indulge in global comfort fare at Wolfgang Puck’s Kitchen.
Since there is so much to take in, we decided to join a guided tour of Grand Rapids with a local guide on our first visit which was a great idea.
What I loved best:
For me, this historic Wisconsin inn near Chicago made for a great weekend retreat. You'll find boutique shops, wineries, and cafés just steps from the front door. The building itself dates back to 1886. I loved how it kept so much of its original character. Inside, you'll find brick walls, wood beams, and antique details. My favorite part was our room for two days, uniquely decorated with a mix of vintage furnishings, a whirlpool tub and a fireplace that made it feel romantic. The inn felt perfect for a romantic weekend escape and for exploring the area’s trails, art galleries, and seasonal festivals. What I loved best:
For me, this inn is one of the best romantic getaways in the USA. It's romantic, peaceful, and a favorite escape I can’t wait to return to!
I especially loved waking up to the complimentary gourmet breakfast, my personal highlight. It was served with so much care and featured fresh, local ingredients—truly one of the best I’ve had at an inn. Whenever I want a Chicago weekend getaway filled with nature, we head to Door County on a road trip.
I loved that our suite for three easy weekend nights came with a full kitchen, a spacious living area, and private balcony. You can cook, relax, and still enjoy resort-style amenities.
I appreciated all the resort extras like the indoor pool, outdoor pool in warm weather, fitness center, game room, and daily breakfast. What I loved best:
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. I ended each evening by unwinding in the whirlpool tub back in my suite (my personal highlight!), feeling grateful for such a relaxing end to the day. 1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
5. If you are planning to visit more than three national parks in the next 12 months, we've found that buying the America the Beautiful Pass is cost effective.
The Washington House Inn - 2 hours from Chicago
The Newport Resort - 4 hours 30 minutes
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