Quick Weekend Family Getaways From Chicago
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Looking for a quick weekend family getaway from Chicago but not sure where to go?
Chicago is a bustling and lively city known for its deep-dish pizza, iconic skyline, and museums. However, sometimes you just need to get away from the hustle and bustle for a relaxing weekend with your family.
If youre looking for a quick getaway weekend destination, here are five great weekend destinations that are all within driving distance from Chicago.
Millennium Park & Lurie Garden
Another must-visit on your trip to Chicago is Millennium Park. The heart of downtown Chicago, this massive urban green space is filled with fun things to do like the Art Institute of Chicago, which is another great family attraction for art lovers, sculptures to see including the Bean, and interactive art pieces to enjoy the Crown Fountain is a favorite in the summer.
You can also roam the Lurie Garden, a free outdoor botanical garden that grows beautiful plants year-round. Its a great place to learn about nature, and makes for some fun photos, too!
Michigan New Buffalo & St Joseph
What I love about going to southwest Michigan is how close it is to the city. Its only 1 1/2 hours to New Buffalo from Chicago and is easily accessible by train for quick weekend getaways from Chicago.
Youll find cute little towns dotting the coast, great beaches along the shores of Lake Michigan, yummy restaurants, shops, and tons of outdoor activities.
New Buffalo is a small town with a cute little downtown area boasting several fun restaurants and a big public beach area. Its a little quieter and laid back than St. Joseph. There are great wineries and blueberry picking in season too.
Want more action? Head a little further north to St. Joseph.
It has a larger downtown area than New Buffalo to explore with tons of shops and restaurants. There is a fun childrens museum too called Curious Kids Museum located downtown.
Plus a short walk away is a cool lighthouse you can walk out to and take pictures along the Lake Michigan Shoreline.
As you head to the beach at Silver Beach County Park, you will pass the Silver Beach Carousel and water pad area for little kids. There is also a great playground on the beach.
The best part is the St. Joseph downtown area is within walking distance of the beach so you can park once and explore the whole area.
Tip: Its a good idea to get to the beach area early in the summer months as parking fills up quickly.
When visiting this area, make sure to check out the Warren Dunes State Park and try to climb the huge sand dunes.
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Weekend Getaways Near Me: Mansion Hill Inn
Located in downtown Madison, Wisconsin, the Mansion Hill Inn is a historic getaway with luxurious guest rooms featuring Frette linens, high-definition flat screen televisions, rain fall showers, and Aveda bath products. If you are planning a romantic getaway, ask for one of the suites with whirlpool baths, in-room gas fireplaces, and access to balconies or verandas with a view. Take advantage of the Pre-Arrival Concierge to customize your stay at the Mansion Hill Inn.
424 N Pinckney St, Madison, WI 53703, 608-255-0172
Illinois Beach State Park

The name of this state park may be a bit misleading as it is one of the only beach-ridge shorelines left in the state. It is home to 6.5 miles of sandy shore and recreation areas, with dunes, swales, marshes, and forests. Illinois Beach State Park has interesting examples of Illinois wildlife like prickly pear cactus, prairie grasses, and cattails. Families can swim, boat, picnic, hike, fish, or camp in the park.
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Where To Stay In Lake Geneva With Kids
When you take a weekendroad trip from Chicago with kids to Lake Geneva, consider staying at the Grand Geneva Resort and Spa and youll never run out of things to do. Thats because the resort offers two golf courses and ski hills for the winter. Alternatively, consider staying at The Abbey Resort which is a destination within itself with its kids camp, live entertainment, boat rentals, and much more.
Navy Pier & Centennial Wheel
The centerpiece of your family vacation to Chicago really should be a visit to Navy Pier. This delightful wonderland is filled with exciting attractions and things to do for families with kids of all ages, with options like theater performances, bike rides, boat cruises, museums, and many more.
One of our favorite things to do is to hop aboard the famed Centennial Wheel Chicagos signature Ferris wheel . You can also dine, shop, and people watch to your hearts content.
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Best Weekend Getaways Near Chicago For Every Traveler
Few destinations can stand up to Chicago, but sometimes we all need a break from the concrete, crowds, and traffic. Some prefer the relaxing vibe of small-town charm, others an escape into the great outdoors, or perhaps a little of both.
With this in mind, we consulted with current and former Chicago residents, pulled out our maps, and mixed it all up in our super scientific trivago lab and came up with the best weekend getaways near Chicago.
Thank You To Our Community
A special thank you to the Families Who Love To Travel Facebook community who shared their travel recommendations for this list of Family Getaways Near Chicago. We could not have compiled such a thoughtful and helpful list without their dedication to our community. Families Who Love To Travel is a group of amazing families who also love adventure and exploring through travel. For more family vacation recommendations and inspiration, be sure to join us on Facebook at Families Who Love To Travel. Were a community of experienced traveling families who love adventure and exploring the world. Plus, follow us on Instagram to connect with other families who love the unique experiences travel has to offer.
*Due to the COVID-19 pandemic, some of the attractions, accommodations, or things to do on this list may be closed. Please ensure availability before making your decision.
*This post may contain affiliate links that may earn us a small commission, at no additional cost to you. Affiliate links in no way inform the hotels, sights, products, or other recommendations included in our articles. All opinions and recommendations expressed here are compiled from submissions submitted by the generous members of our Families Who Love To Travel community.
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The Inn At Irish Hollow And Country English Cottages
Irish Hollow is a beautiful bed and breakfast perfect for a romantic getaway that sits on a 500-acre farm. Guests can choose to stay in one of the five private cottages or one of the guest rooms in the Main Inn. These cozy, intimate rooms have iron or claw foot bathtubs, enhanced showers, a sitting area, gas fireplaces, and modern amenities. The cottages vary, but may have king four-poster beds, oriental rugs, private porches, double whirlpool baths, iPod docks, Wi-Fi, and more.
You can also have body work done at the inn. Breakfast is included with your stay and it is hand-made using natural ingredients. You can choose a continental breakfast delivered to your room, the Full Country Gourmet Breakfast in the Old General Store, or a healthy version of this full breakfast. Guests can also order additional meals, including picnics, wine and cheese. Dinner packages start at $345 per night.
2800 S. Irish Hollow Rd., Galena IL, 815-777-6000
Madison Wisconsin: 147 Miles Northwest Of Chicago
This town embraces the quirky and classy in its arts, museums, shops, dining venues and outdoor activities. Even its farmers market is a Bohemian rhapsody of local produce, entertainment, art and political activism on the state capitol square. Wander the paths and trails at Olbrich Botanical Gardens or the University of Wisconsin Arboretum admire the art at Chazen Museum of Art or the Madison Museum of Contemporary Art take a leisurely cruise around Lake Mendota or Menona and be sure to work up an appetite-Madison’s 600-plus restaurants offer something for every taste.
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Resorts Near Me: Farmers Guest House
Farmers Guest House is located in historic downtown Galena, giving guests easy access to nearby attractions. Each of the nine rooms and suites is tastefully decorated, providing an intimate setting perfect for couples. All rooms have flat-screen TVs with Blu-Ray/DVD players to watch movies from the inns collection and there is Wi-Fi throughout the property. Other room amenities include private baths, luxurious bath amenities, individual outlets, irons, hairdryers, and plenty of outlets.
The common areas include the Spa Studio, private gardens, and numerous patios. In the morning, guests enjoy a full breakfast with a signature entrée, homemade pastries or bread, fruit, juice, and homemade granola. There is also Wine time every evening with cheese and wine, as well as fresh cookies at night. Guests have access to soda, tea, coffee, and bottled water. Rooms start at $179 per night.
344 Spring St., Galena IL, 815-777-3456
Getaways From Chicago Illinois: Vrooman Mansion

The Vrooman Mansion is a historic bed and breakfast right in Bloomington/Normal. The historic estate offers luxury and privacy with easy access to attractions, restaurants, and shops. The majority of the decorations in the spacious guest rooms are antique period furniture, with each room featuring its own theme. The suites have down pillows, soft fluffy towels, high-quality linens, microfiber robes, and free Wi-Fi. There are five suites and rooms in the Mansion and two in the carriage house.
The numerous common areas include the Safe Room, the Library, the Foyer, the Music Room, the Dining Room, and the Parlor. Throughout the day, you can enjoy bottled water, soft drinks, and snacks and a full gourmet breakfast is included in every stay. Breakfast features tea, coffee, or cocoa, juice, fruit, and a hot entrée. Rates start at $110 per night.
701 East Taylor St., Bloomington IL, 309-828-8816
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Summary: Its So Easy To Find Road Trips Near You
While living in Chicago, it was incredible that I had so many road trip destinations near me. This list doesnt even cover them all.
Other possibilities include short Illinois road trips to places like Galena, Champaign, Bloomington, Normal, and Peoria. The University of Illinois campus in Champaign is particularly noteworthy. Galena is home to statues of Ulysses Grant and his wife Julia.
If youve got at least 5 days on your hands, consider other weekend trips from Chicago to Memphis, Atlanta, Charlotte, or Virginia Beach. Make this the summer of the road trip!
And if you want to get really crazy, heres a detailed guide to driving from Chicago to Seattle
Do you have any other suggestions for great road trips from Chicago? Leave a comment and let us know!
Chicago Weekend Getaways For Families
Chicago is easily one of Americas most family-friendly and culturally diverse cities. Its home to The Willis Tower , which is the second tallest building in the U.S. Its also home to delicious deep-dish pizza and a plethora of interesting culture, attractions and family fun.
Families making their first trip to the Windy City may be a bit overwhelmed by how much there is to see and do, but dont worry were here to help! Welcome to a Chicago weekend getaway with kids.
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Midwest Destinations To Visit With Kids In 2022
These Midwest destinations offer a fun getaway for families.
Do you want to get away, but have no idea where to go? The Midwest offers so many destinations the hard part is trying to figure out where to go. We made it easier for you by picking some of the best family vacations that you can also double as a road trip.
For each destination, we provided a mini kid-friendly itinerary on what to do, places to eat and where to stay. Here are a few ideas to help you plan your next family vacation in 2022.
Note: Were updating our website as quickly as we can, but changes may occur due to COVID-19. Please double check before heading out for the most updated information on safety precautions, travel advisories and any last-minute closings. Stay safe!
Starved Rock State Park Illinois
Wander through towering trees to find waterfalls and wildlife at Starved Rock State Park. This park, located on the Illinois River, is situated about an hour and a half from Chicago, making it the perfect choice when you want to trade skyscrapers for the great outdoors for the weekend. In the spring, the waterfalls are especially active, thanks to heavy rains, and in the fall, the leaves turn beautiful shades of orange, red, and yellow. Stay within the state park at the Starved Rock Lodge, or opt to spend the night in nearby Ottawa, a charming little town with restaurants, shops, and more.
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How To Get Around Chicago
Chicago is a walkable city meaning that when staying downtown, the majority of the popular restaurants, sites, and attractions are all within walking distance to one another.
If staying downtown you simply do not need a car to get around once there.
For longer stretches, Uber vehicles are highly prevalent and can typically be found within 2 3 minutes of any given address.
In addition, Chicago is well-known for its convenient street system and its fantastic public transit system.
Toronto & Niagara Falls
Chicagoans rarely consider Toronto, Canada as a road trip option, but its only 8 hours away if traffic and border crossings cooperate. Add another 90 minutes to reach Niagara Falls, one of the great natural wonders of North America.
Chicago and Toronto are incredibly similar. They have nearly identical-sized populations . Both have great museums, outdoor adventures, cultural experiences, culinary delights, and vibrant nightlife.
A few things Toronto has that Chicago doesnt: The Hockey Hall of Fame, the CN Tower, and a chance to paddle in the Harbor Islands. For a silly tourist attraction, check out the Bata Shoe Museum.
On the way to Toronto, youll pass through the town of London, Ontario, Canada. This city has lots of interesting attractions and fun things to do, so check it out!
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Weekend Getaways From Chicago: The Abbey Resort
The Abbey Resort is a full service getaway on 90 scenic acres near the Fontana harbor, offering 334 deluxe guestrooms, 13 spacious suites and 13 villas. The 35,000-square-foot Avani Spa offers massages, facials, wraps, aromatherapy and saunas on your weekend trip.
Resort facilities include a fitness center, aerobic studio, indoor and outdoor swimming pools, a disk golf course, and a games arcade for kids. Dining options range from casual cafes to gourmet restaurants, including 240 West, Café Latte, the Waterfront Restaurant Bar & Grill, Bar West and Porto. Weekend activities include watersports, bike rides, golf, walking and jogging around the lake. If you are looking for affordable resorts near Chicago, rooms start at $89 per night.
269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125
D Rock National Lakeshore Michigan

Distance from Chicago: 380 miles northeast, 6 hour driveThe upper peninsula of Michigan is a truly spectacular piece of the Midwest that is often overlooked by Chicagoans, as it does require more road time. But dont let the distance discourage you. Pictured Rocks National Lakeshore includes 42 miles of glorious views along the southern dip of Lake Superior, and really packs a punch, with gushing waterfalls, pristine lakes, endless rugged forest, and multi-colored rocky ridges with some as high as 200 feet. You wont want to miss the Miners Castle and Chapel Rock, both impressive craggy cliffs which stand apart from the rest because of their peculiar shapes and size. Whether you want to hike through the forest, kayak along the shoreline, cruise on a boat, or bike some backroads trails, this natural paradise will keep you occupied for a long summer weekend for sure. Fun fact, this area is widely known by historians to be the burial ground of many old ships dating back to as early as 1860. Book a tour on a boat with a glass floor to see these huge relics while you float above. Munising Township is stocked with restaurants, bars, and humble accommodations if camping doesn’t sound appealing. Also, Hiawatha National Forest is 15 miles away so you get two for the price of one.
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Best Summer Day Trips From Chicago
After a year at home, it’s time to hit the open road! While getting out of town for a week can sometimes be impossible, just a day away can refresh and recharge. Weve gathered up 20 summer day trips from Chicago that have kids in the car for a couple of hours and still offer up a change of scene and plenty of fun. From beaches to hikes to slides, we’ve rounded up some fun-filled day trips away from the city for the whole family to enjoy.
For more local trip ideas check out our Midwest Travel Guide or our list of the Best Lakeside Resorts for Families.
Where To Stay In Indianapolis With Kids
Book your stay at theCourtyard Indianapolis Downtown or, book theResidence Inn Indianapolis Downtown on the Canalwith Travelocity today!
When location matters, stay at Indianapolis Courtyard Indianapolis Downtown and you will be within walking distance of restaurants, have access to the sky bridge to the Indiana Convention Center. Plus, its less than two miles from the Indianapolis Zoo. Another hotel with a pretty location along the downtown canal is the Residence Inn Indianapolis Downtown on the Canal.
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