Planning a weekend getaway from the bustling city of Chicago? We’ve got you covered! Whether you’re looking for a cozy mountainside ski cabin or a beachfront boutique hotel, our guide to the best weekend getaways from Chicago has something that will bring out the explorer in anyone.
From skiing to swimming and museums to golf courses, this is your ultimate guide to an unforgettable trip outside The Windy City.
Take a short drive into Michigan’s wine country and explore some of the state’s most beautiful wineries. Hit the slopes at Timber Ridge Resort or discover hidden treasures while shopping in downtown St. Joseph.
With affordable room rates and packages galore, there are plenty of ways to make your dream weekend getaway absolutely perfect without breaking the bank.
If you’re feeling daring, sign up for some rock climbing or take a kayak ride along Lake Michigan’s shores!
No matter what kind of adventure you choose, don’t forget to call ahead and confirm any attractions, restaurants, or resorts first.
Best weekend getaways from chicago
1. The Knickerbocker on the Lake
The Knickerbocker on the Lake is the perfect spot for all your travel adventures! Located in downtown Milwaukee, you’ll be in the heart of the action, just a short walk away from some of the city’s best restaurants, museums, theaters, and transportation options.
Our cozy hotel offers 160 beautifully appointed rooms and suites featuring period-influenced furniture combined with all the modern conveniences.
Kick back in our comfortable and spacious guest rooms complete with full kitchenettes and free Wi-Fi – perfect for business travelers and families – or upgrade to one of the luxurious lake view suites with stunning views of Lake Michigan.
We offer plenty of amenities to make your stay extra special, including a state-of-the-art fitness center, rental bicycles to explore the city on two wheels, grab ‘n’ go breakfasts, in-room dining service, an outdoor terrace perfect for evening cocktails or people watching – you name it! Even better?
There’s a friendly staff always on hand ready to make sure your Wisconsin getaway is as pleasant as possible.
If you are looking to get away and make some memories but don’t want to splash out a fortune, The Knickerbocker on the Lake is just for you!
This full-service resort offers endless possibilities for relaxation, fun, and adventure. With luxurious services at the Knick Spa & Salon, a state-of-the-art fitness center with 24-hour access, and tailored clothing and dry cleaning, you simply won’t be able to resist.
And if you’re really into fine dining, there’s no equal to our own Knick Restaurant! On weekends don’t miss the extraordinary Sunday brunch they offer – once-in-a lifetime gastronomic experience!
If you seek o enjoyable weekend getaways that don’t put too much strain on the wallet – The Knickerbocker on the Lake is your go to answer.
It’s magical how much this place has to offer! So start packing – lets make those Happy Traveling memories together!
Address: 1028 E Juneau Ave, Milwaukee, WI 53202
2. The Newport Resort
Welcome to the Newport Resort, where your perfect family vacation or romantic escape awaits! Located in Door County, Wisconsin and just minutes from the beach, we make it easy to find relaxation and fun.
This resort has 59 beautiful rooms and suites with modern amenities like whirlpool tubs, cozy sitting areas, and kitchenettes for your convenience. Enjoy a dip in the indoor pool, get some exercise in the fitness center, or challenge the family in ther game room!
The library is the ideal spot for some peaceful reading, while the lobby lounge makes it easy to kick back with a refreshing drink before exploring Egg Harbor. Don’t forget the tranquil garden – perfect for an evening stroll – and all of the outdoor adventure available within walking distance of the resort.
From breathtaking beaches and renowned golf courses to snowshoeing through state parks in the wintertime, you’ll be sure to make lasting memories at any time of year.
Happy traveling starts here at The Newport Resort! Join us for your next vacation or getaway – you won’t regret it!
Address: 7888 Church St, Egg Harbor, WI 54209
3. The Abbey Resort
Experience the perfect getaway by booking a trip to The Abbey Resort! Located near the Fontana harbor, this stunning full-service resort is situated on 90 picturesque acres and promises a memorable vacation.
You will have your choice of 334 deluxe guestrooms, 13 spacious suites and 13 villas, all with unbeatable views. Get in touch with your inner Zen by spending some time at The Avani Spa’s 35,000-square-foot facility — offering massages, facials, wraps, aromatherapy and saunas on your weekend trip.
Not to mention their selection of fitness centers and aerobic studios! If you worked up an appetite from all this activity, you’ll be delighted that The Abbey Resort has plenty of delicious dining options ranging from casual cafes to gourmet restaurants; including the Waterfront Restaurant Bar & Grill and Bar West for an extra special night out.
And if you’re feeling adventurous, there are plenty of outdoor activities available such as watersports, bike rides, golfing, walking or jogging by the lake. So don’t hesitate to treat yourself to a vacation at The Abbey Resort – book now so you can take advantage of amazing room rates from $89 per night! Happy Travels!
Address: 269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125
4. Grand Traverse Resort
At Grand Traverse Resort, you have all the amenities at your fingertips for a great travel getaway. Nestled on 1400 beautiful acres on the shores of Lake Michigan, this resort offers unparalleled relaxation and recreation for everyone in the family.
Take your pick from four amazing 18-hole golf courses, designed and maintained with love by legendary golfers Jack Nicklaus, Gary Player, and William Newcomb.
Perfect your game even more with the one-of-a-kind Grand Traverse Golf Academy. Whatever level golfer you are, you will be able to access world class instruction specifically tailored to suit your needs.
Beyond golfing we also offer a perfect escape: our 100,000 square foot spa complex featuring treatment space, workout facilities, and a tennis center.
Take a break before your treatment and take advantage of our two indoor swimming pools, four whirlpools, sauna and relaxation room.
Get active by taking part in one of our yoga classes or playing some invigorating tennis. What more could you want when looking to improve your overall fitness?
Accommodations include condos right by the beach and fairways, equipped with kitchenettes, dining areas, and a comfy queen-size sofa sleeper in the living room.
Enjoy a range of delicious restaurant menus available throughout your stay. Tower and hotel rooms also provide elevated lake views centrally located near restaurants, spas, and shops. Perfect for families or couples!
Don’t forget to ask about seasonal deals, specials and packages to make the most out of your trip. At Grand Traverse Resort, a wonderful anxiety-free travel experience awaits you!
So come join us at Grand Traverse Resort for the perfect combination of tranquil escapes complete with award winning recreation – ready whenever you are!
Address: 100 Grand Traverse Resort Village Blvd, Acme, MI 49610
5. Grand Geneva Resort
Whether you’re looking for adventure or romance, the Grand Geneva Resort and Spa is the perfect weekend getaway!
Located between Chicago and Milwaukee, this resort offers an irresistible mix of activities to ensure you make the most out of your trip.
Take on a great challenge on the golf courses; relax in one of two hot tubs at Moose Mountain Falls Waterpark; explore the area on a lake cruise; and enjoy shopping Downtown for unique items.
For a special family vacation, take advantage of 50,000 square feet of heated watersides including tubing on the lazy river.
For winter visits, get your adrenaline pumping with downhill skiing, snowboarding and cross-country skiing at The Mountain Top.
Feel rejuvenated with a workout in our fitness center or indulge in some pampering in our spa. No matter what type of traveler you are, Grand Geneva has something in store just for you!
So what are you waiting for? Start happy traveling today with Grand Geneva Resort and Spa!
6. The American Club, Kohler
Experience the perfect escape from the hustle and bustle of everyday life at The American Club, Kohler!
Tucked away in a peaceful Wisconsin setting in about two and a half hours from Chicago, this premier resort offers something for everyone—whether traveling with family, as a couple or just for a relaxing solo getaway.
For lovers of the great outdoors, there’s never a dull moment at The American Club. Take advantage of golf packages, including golf academy specifically tailored to women, golf specials and more.
End your day with Yoga on the Lake – their amazing premier yoga studio offering 20 classes per week.
If you’d rather slow down the pace and take time out to truly relax then why not indulge in their newly renovated couples suite and experience side-by-side massage treatments?
You won’t want to miss out on the Knox Lager Spa either – an ultimate destination for complete sensory joy featuring an impressive glass enclosed rooftop deck with luxurious whirlpool, inviting fireplace and stylish lounge seats.
This summer don’t wait around – start planning your happy traveling journey now.
For unbeatable pampering combined with outdoor adventures look no further than The American Club – near Chicago – where amazing memories await.
7. The Green Tree Inn
Your search for your next travel destination stops here! The Green Tree Inn nestled in the picturesque Elsah valley is the perfect spot to spend a relaxing weekend getaway or vacation.
Offering five unique and luxurious rooms with queen or double beds, cozy TVs, private baths, and air conditioning; you’re guaranteed an unbeatable stay of comfort and tranquility.
Plus, Wi-Fi and a communal satellite TV are available throughout the property as well as snacks, coffee, cider, and tea – making it almost feel like you never have to leave.
But why stay indoors when there’s so much waiting just outside your door? Lace up your shoes and go explore the beautiful gorge nestled near the inn or borrow one of their bikes and ride through the winding paths of Elsah.
Wherever you decide to wander, it’ll be hard not to take in all breathtaking sights before returning for an evening massage.
Ready for more?
Challenge a friend to a game of checkers in their cozy antique room or relax on their deck with views that will take your breath away–a hot cup of cocoa in hand.
The Green Tree Inn really has it all—including homemade breakfast in mornings followed by homemade dinners which freshen your palate after being out exploring all day.
So book now at The Green Tree Inn because happy travelers know this is the absolute best place to be!
Address: 15 Mill St., Elsah IL, 618-374-2821
8. Seven Oaks
Welcome to Seven Oaks! If you’re looking for a romantic getaway near Chicago, this is the place for you. This adult-only cottage suites are total luxury, with their charming front porches, stone fireplaces and king-sized beds complete with luxury linens.
Whether you are looking for peace and quiet or an adventurous night out on the town, It has something for everyone.
Unwind in the peaceful garden which features a soothing water feature, a warm and inviting fire pit, and comfortable lounging chairs.
Take a stroll downtown to experience Lake Geneva’s excellent restaurant selection, play a round of golf on one of the local courses, visit nearby day spas or go biking, hiking or skiing (in the winter!).
The possibilities here at Seven Oaks are truly endless!
We invite you to treat yourself to a tranquil escape right in nature’s backyard.
Address: 682 S. Wells Street, Lake Geneva, WI 53147, 262-248-4006