Chicago is characterized by stunning architecture and magnificent water views. It is the third most populated city in the United States, serving as a hub for technology, culture, commerce, and transportation.
Chicago is best known for skyscrapers and Lake Michigan. The vibrant city pulls in millions of travelers who want to experience the various museums, art galleries, and live music venues in town.
Beyond waterfront skyscrapers, Chicago is known for its Major League Baseball teams and deep dish pizza. This midwest region has plenty of exciting activities for visiting families to enjoy. There are endless experiences for people of all ages to explore in just a few short days.
The average cost of a four-night trip to Chicago for one person is $915. Couples can expect to pay at least $1,317. This excludes airfare. The average price for Chicago’s peak season from July to August is around $1,659. Alternatively, traveling during the low season of November through March will cost a tourist about $714.
The Abbey Resort is our top pick for the best all-inclusive family resort in the Chicago area for a reason. It has plenty to offer beyond architecture and lake views.
1. The Abbey Resort
The Abbey Resort is our top choice for an all-inclusive family resort in the Chicago area. It features exquisite services and amenities that can’t be found anywhere else.
The Abbey Resort stands out for its full-service spa on site. Guests can take advantage of unique spa packages, along with direct access to a beautiful lake and amenities such as campfires and lakeside dining. There are plenty of area activities to participate in during the day, from hiking and swimming to zip lining through the trees.
Restaurants at The Abbey Resort include a premier steakhouse. There are also several options scattered across the lakefront for beautiful scenic views while dining.
Accommodations at The Abbey Resort include plush King beds with giant windows, walk out balconies, and unobstructed views of the lake. Guests have access to high speed wifi and on-demand movies.m inside the room.
The starting cost for a four-night stay at The Abbey Resort is approximately $897.
Address: 269 Fontana Blvd, Fontana, WI 53125-9604
Phone: (800) 709-1323
Website: The Abbey
Booking.com Rating: 7.8
2. Indian Lakes Hotel
Indian Lakes Hotel is set apart by its mouthwatering dining options and access to area activities. Families traveling near Chicago will have a blast at this resort.
Indian Lakes Hotel is located less than an hour away from the airport and Downtown Chicago. Those visiting the area can maximize their stay at Indian Lakes, all while taking advantage of the on-site pool, spa, and continental breakfast.
In addition to the city of Chicago, the hotel is close to many area attractions including Bloomers Stadium and Dave & Busters.
Restaurants at Indian Lakes Hotel include a wide selection of dining options in the area. All guests of the resort are given complimentary breakfast every morning made by the hotel kitchen, including pancakes, fruit, and other American breakfast classics.
Accommodations at Indian Lakes Hotel include standard hotel room amenities with flat screen TV’s, cable channels, a hair drier, and coffee maker. Suites are available on the property with one to two connecting bedrooms inside.
The starting cost for a four-night stay at Indian Lakes Hotel is approximately $539.
Address: 250 W Schick Rd, Bloomingdale, IL 60108-1228
Phone: (855) 605-0316
Website: Indian Lakes Hotel
Booking.com Rating: 7.5
3. Eaglewood Resort and Spa
Eaglewood Resort and Spa is renowned for its excellent hospitality. Staff will treat you like family and make you feel at home.
Eaglewood Resort and Spa has a wide range of amenities for guests to enjoy, from a heated indoor pool to golf course and six-lane bowling alley.
There are endless things to do on the property, including hosting a private event. The full-service spa features a menu of relaxing massages and body treatments for the adults.
Restaurants at Eaglewood Resort and Spa include the Prairie River Restaurant, offering guests a taste of authentic Midwest cuisine. There is also a full service bar on site.
Accommodations at Eaglewood Resort and Spa include cozy guest rooms with dedicated workstations and a lounge chair with an ottoman. From the plush King bed, a flat screen TV with cable channels is viewable.
The starting cost for a four-night stay at the Eaglewood Resort and Spa is approximately $1,035.
Address: 1401 Nordic Rd, Itasca, IL 60143-2499
Phone: (877) 285-6735
Website: Eaglewood Resort and Spa
Booking.com Rating: 8.1
4. Palmer House, a Hilton Hotel
Palmer House certainly lives up to the Hilton name. The worldwide hotel brand remains consistent in its offerings at other properties.
The Palmer House is situated in a historic location in downtown Chicago. Visiting families can take advantage of the proximity to area attractions, including the Theater District and Millennium Park. Without having to leave the hotel, guests can take advantage of the lobby bar, pool, fitness center, and spa.
Restaurants at Palmer House include Lockwood Restaurant and Lockwood Lobby Bar. The restaurant offers a variety of cuisine, with their most popular menu item benign their brownie. Be sure to try a piece of this famous treat before you go!
Accommodations at Palmer House include elegantly decorated guest rooms. Furnishings are classy and minimal, and include all of the basic hotel amenities you can expect.
The starting cost for a four-night stay at Palmer House, a Hilton Hotel is approximately $1,098.
Address: 17 East Monroe Street, Chicago, IL 60603
Phone: (855) 695-0216
Website: Palmer House, a Hilton Hotel
Booking.com Rating: 7.9
5. Worldmark Galena
Worldmark Galena is the epitome of class in the Pocono Mountains. Visitors of this resort will soon learn why the city generates so much tourist traffic every year.
Worldmark Galena is nestled in the trees away from the noise of the city. The town is the second most visited place in the state of Illinois for a reason. The resort is managed by Wyndham, ensuring a consistent level of quality. Some of the amenities guests can enjoy on the property include a spa, pool, and several restaurants.
Restaurants at Worldmark Galena include Highlands Restaurant and Paisanos Restaurant. There is a string of restaurants available in the area as well that are easily accessible for meals away from the resort.
Accommodations at Worldmark Galena consist of a selection of beautifully decorated guest rooms. Each well-appointed suite comes with the basis, from shampoo and a hair dryer to iron and ironing board.
The starting cost for a four-night stay at Worldmark Galena is approximately $996.
Address: 5129 W Longhollow Rd, Galena, IL 61036-9383
Phone: (866) 723-9878
Website: Worldmark Galena
Booking.com Rating: 8.6
6. Embassy Suites Chicago Downtown
Embassy Suites Chicago Downtown is another reliable accommodation option for families visiting Chicago. Stay in the heart of the city to experience everything it has to offer during your trip.
Embassy Suites Chicago Downtown, managed by a trusted national hotel provider, fits the bill of an affordable and stylish accommodation.
It is located steps away from Lake Michigan, providing direct access to the best attractions. Inside the hotel, guests can take advantage of an indoor pool, business center, and complimentary evening reception.
Restaurants at Embassy Suites Chicago Downtown include free continental breakfast for all guests every morning. The hotel serves breakfast classics such as sausages, eggs, pancakes, and oatmeal, in addition to fruit and dry cereal. The downtown area is optimal for exploring nearby restaurants after eating a free made-to-order breakfast.
Accommodations at Embassy Suites Chicago Downtown come in a variety of space options. Families can opt for several singular suites or book connecting rooms. Larger rooms are available to rent for large families.
The starting cost for a four-night stay at Embassy Suites Chicago Downtown is approximately $789.
Address: 600 North State Street, Chicago, IL 60654
Phone: (855) 695-0419
Website: Embassy Suites Chicago Downtown
Booking.com Rating: 8.1
7. Osthoff Resort
Family travelers seeking an unforgettable hotel experience near Chicago should stay at the Osthoff Resort. The AAA Diamond Resort is a suitable place to make memories while visiting in the area.
Osthoff Resort is a highly rated accommodation in the Chicago area. There are many things to do on and off the resort at an hourly rate, including mountain biking and tandem biking. There is a spa on the property, along with many things to do in the area from gold to paddleboarding.
Restaurants at Osthoff Resort include regional cuisine served at Concourse Restaurant & Lounge and Otto’s Restaurant. Room service is also available, along with the Elk Room to rent out private events if needed.
Accommodations at Osthoff Resort include cozy guest suite cabins with views of the lake. Guests can enjoy living areas in front of large windows overlooking nature.
The starting cost for a four-night stay at Osthoff Resort is approximately $1,216.
Address: 101 Osthoff Ave, Elkhart Lake, WI 53020-1976
Phone: (877) 734-0381
Website: Osthoff Resort
Booking.com Rating: 7.5
8. Chestnut Mountain Resort
Chestnut Mountain Resort provides all-inclusive resort amenities at a reasonable price. It is known for its high quality amenities and unique outdoor activities.
Chestnut Mountain Resort features a snowboarding park and an alpine slide on the property. Families are in for several days of fun at this resort, with rates and packages available for daily outdoor activities.
Restaurants at Chestnut Mountain Resort include the Sunset Grille, a cozy dining area serving classics everyone will enjoy. Some of the most popular menu offerings include steaks and salads.
Accommodations at Chestnut Mountain Resort consist of guest rooms with extra soft king beds and free wifi. Basic necessities including toiletries and hair dryers are also available.
The starting cost for a four-night stay at Chestnut Mountain Resort is approximately $836.
Address: 8700 Chestnut Dr, Galena, IL 61036-8787
Phone: (815) 777-1320
Website: Chestnut Mountain Resort
Booking.com Rating: 7.8
9. Hyatt Regency Chicago
Hyatt Regency Chicago is an upscale family establishment. The resort provides a safe and convenient lodging option in the heart the city.
Hyatt Regency Chicago is located steps away from Chicago’s Riverwalk and pier. Magnificent Mile is a short walk away, but there are plenty of amenities to enjoy at the hotel. The resort features a concierge, business center, and fitness center.
Restaurants at Hyatt Regency Chicago include American Craft Kitchen & Bar and Market Chicago. There is also a bar and indoor sushi restaurant on the property.
Accommodations at Hyatt Regency Chicago include attractive guest rooms with gorgeous water views. In addition to internet access and a digital key, the hotel offers digital check in for convenience.
The starting cost for a four-night stay at Hyatt Regency Chicago is approximately $1,315.
Address: 151 East Wacker Drive, Chicago, IL 60601-3709
Phone: (888) 882-1234
Website: Hyatt Regency Chicago
Booking.com Rating: 8.2
10. Lincolnshire Marriott Resort
Lincolnshire Marriott Resort is a classy establishment with easy access to all of the best attractions. It is one of the Midwest’s finest accommodations.
Lincolnshire Marriott Resort is tucked away in a quiet Chicago suburb. The location is unmatched when it comes to privacy and proximity to attractions. The 175 acre property features a golf course and several meeting rooms for private events.
Restaurants at Lincolnshire Marriott Resort include Wrights Brew & Bistro and Three Embers Restaurant. There is a classy bar in the lobby, along with a Starbucks on the property for convenience.
Accommodations at Lincolnshire Marriott Resort include floor to ceiling sliding glass doors with walk out balconies overlooking the golf course. Guests can choose from single or double beds, or opt for a larger suite with an additional sofa bed.
The starting cost for a four-night stay at Lincolnshire Marriott Resort is approximately $798.
Address: 10 Marriott Dr, Lincolnshire, IL 60069-3700
Phone: (744) 631-0595
Website: Lincolnshire Marriott Resort
Booking.com Rating: 7.9
11. Congress Plaza Hotel
Families can enjoy a long list of amenities in this all-inclusive environment. From outdoor activities to in-house events, there is something for everyone here.
Congress Plaza Hotel is a legendary resort overlooking Lake Michigan with historical significance. Families can lodge in a place where former presidents and celebrities have traveled. The vintage icon hotel features a fully-furnished lobby with concierge and free wifi. A 24 hour fitness center is paired with an on-site fry cleaning service for convenience.
Restaurants at Congress Plaza Hotel include Gazebo, a lovely restaurant serving breakfast and pastries in a casual dining room. Guests can indulge in afternoon and evening meals at Rafael’s or visit the Congress Lounge for any-time comfort food.
Accommodations at Congress Plaza Hotel include historic rooms with modern updates and amenities. The classic decor shines the most, with varying amounts of space available, including a large family suite with separate bedrooms.
The starting cost for a four-night stay at Congress Plaza Hotel is approximately $1,678.
Address: 520 South Michigan Avenue, Chicago, IL 60605-1602
Phone: (312) 427-3800
Website: Congress Plaza Hotel
Booking.com Rating: 8.2
12. Timber Ridge Lodge & Waterpark
Timber Ridge Lodge & Park is an excellent place for families traveling near Chicago. Voted one of the best water parks in the country, this Lake Geneva property has it all for your next family vacation.
Timber Ridge Lodge & Waterpark provides a serene natural getaway with access to exciting activities and amenities. One of the best features this place has to offer is its on-site waterpark on the 1,300 acre property.
There is plenty to explore every day at Timber Ridge, from outdoor recreational activities to nearby sights and excursions in Chicago and Milwaukee.
Restaurants at Timber Ridge Lodge & Waterpark include Smokey’s BBQ House and Hungry Moose. Additional dining options from steakhouses to American cuisine are available in the area, catering to every palate with picky eaters in mind.
Accommodations at Timber Ridge Lodge & Waterpark include over 200 suites with spacious floor plans and full kitchens. Every room comes with a fireplace and complimentary daily housekeeping services.
The starting cost for a four-night stay at Timber Ridge Lodge is approximately $720.
Address: 7020 Grand Geneva Way, Lake Geneva, WI 53147-5105
Phone: (262) 249-3400
Website: Timber Ridge Lodge
Booking.com Rating: 8.1
13. The Glen Club
The Glen Club is a premier family vacation destination in Glenview. It is the perfect setting to create memories for years to come.
At The Glen Club, parents and children can enjoy several acres of open space for relaxation and recreation. The golf course property features a full range of activities, from hole-by-hole games to golf lessons and special golf outings. It is the perfect venue for sports-lovers and active families.
Restaurants at The Glen Club include The Glen Club Grill, a convenient source of American cuisine and casual dining. Guests can take advantage of a full menu featuring many choices for kids without having to leave the resort property.
Accommodations at The Glen Club include upscale boutique room options. Each suite is tastefully decorated and comes with clubhouse access and golf course views.
The starting cost for a four-night stay at The Glen Club is approximately $752.
Address: 2901 W Lake Ave, Glenview, IL 60026-1264
Phone: (847) 724-7272
Website: The Glen Club
Booking.com Rating: 7.6
14. Illinois Beach Hotel
The only resort located on Lake Michigan, this hotel provides an experience you can’t get anywhere else. World-class service combined with its unique location make this resort a top choice in the Chicago area.
Illinois Beach Hotel features over 6 miles of beautiful sand on the shores of Lake Michigan. Guests can take advantage of direct access to the private beach, along with a network of walking trails and the best fishing spots in the area. Things to do around the hotel include Six Flags, Genesee Theatre, and Edge of Escape rooms for family fun.
Restaurants at Illinois Beach Hotel include an on-site restaurant and bar for lunch and dinner. It is open to guests on weekdays only. In between these times, guests can visit Nolan’s on site for daily burger and prime rib specials.
Accommodations at Illinois Beach Hotel include modern and spacious rooms with water or park views from the window. Larger suites feature panoramic windows and walk out balconies, with all of the basic comforts from a TV to a coffee maker.
The starting cost for a four-night stay at Illinois Beach Hotel is approximately $752.
Address: 1 Lake Front Drive, Illinois Beach Resort and Conference Center, Zion, IL
Phone: (866) 452-3224
Website: Illinois Beach Hotel
Booking.com Rating: 8.6
15. Hyatt House Chicago/Evanston
Hyatt House Chicago/Evanston is as close as you can get to all the action. Families love the convenient location and welcoming staff at this all-inclusive resort.
Hyatt House Chicago/Evanston has plenty to offer its family guests, from fitness and business centers to digital room check in. The property features several restaurants and bars, located just a short drive away from nearby attractions. Points of interest in the general area include Sherman Plaza and the purple line.
Restaurants at Hyatt House Chicago/Evanston include a bar, market, and complimentary morning breakfast buffet. Guests can elect to cook their own meals, taking advantage of the grocery delivery service offered.
Accommodations at Hyatt House Chicago/Evanston feature the modern conveniences of mobile room keys and check in. Spacious suites contain one or more separate bedrooms for family travelers to take advantage of. The largest options contain kitchens and furnished living areas.
The starting cost for a four-night stay at Hyatt House Chicago/Evanston is approximately $844.
Address: 1515 Chicago Ave, Evanston, IL 60201-4405
Phone: (847) 864-2300
Website: Hyatt House Chicago/Evanston
Booking.com Rating: 7.6
16. Graduate Evanston
Graduate Evanston provides a nostalgic and comfortable stay for families in Illinois. From delicious food to friendly staff, there are many attractive perks that will make your stay a breeze.
Graduate Evanston is part of a nationally recognized hotel chain, renowned for its excellent service and consistent offerings between locations across the country. When staying at a Graduate hotel, guests can expect organized activities such as picnic lunches and football themed events.
Restaurants at Graduate Evanston include The Homestead Room, serving American-style comfort food with cocktails from the bar. The cozy, home-like eatery is also open in the mornings for delicious coffee and snacks.
Accommodations at Graduate Evanston include studio suites and larger King rooms for additional space. Families can rent out the Graduate Corner King to take advantage of a living area, desk space, and wood burning fireplace in the room.
The starting cost for a four-night stay at Graduate Evanston is approximately $890.
Address: 1625 Hinman Ave, Evanston, IL 60201-6021
Phone: (847) 475-3300
Website: Graduate Evanston
Booking.com Rating: 8.0
17. Victorian Bay Resort
The Victorian Bay Resort is a lovely backdrop for a family vacation near Chicago. Bordering the picturesque Indiana Beach Boardwalk, there are endless things to do from sunrise to sunset.
The Victorian Bay Resort is located in Monticello, Indiana, a beautiful beach town near Chicago with a popular boardwalk and many other attractions to offer family travelers.
A stay in Monticello can include spending time on the beach and exploring nearby shops and restaurants. Popular water activities in the area include paddle boarding and surfing.
Restaurants at Victorian Bay Resort consist of pubs with delicious dishes and beverages to match. Some of the most popular offerings are Beaver’s Pub and Whiskey and Wine Saloon.
Accommodations at Victorian Bay Resort include comfortable rooms in a laid back environment. Families can choose from suites with different amounts of space, including air conditioning, a refrigerator, and microwave. Cozy living spaces make it convenient to socialize and cook meals if desired.
The starting cost for a four-night stay at Victorian Bay Resort is approximately $715.
Address: 5116 E Indiana Beach Rd, Monticello, IN 47960-1264
Phone: (888) 882-2267
Website: Victorian Bay Resort
Booking.com Rating: 7.2
18. Lakeshore Camp Resort
Lakeshore Camp Resort provides a unique lodging experience in Portage, Indiana. Families who enjoy outdoor adventures will find exactly what they seek on this beautiful property.
Lakeshore Camp Resort is a campsite rental park with over 100 individual spots near Chicago in neighboring Indiana. This location stands out against other family lodging options in the area.
It does not fit the description of the average hotel room or vacation rental. Families who stay here have access to area attractions and 22 acres of lakes, pools, golfing, beaches, fishing, and more.
Restaurants at Lakeshore Camp Resort consist of local eateries with cuisine options ranging from hot dogs to classic American comfort food.
The resort is conveniently located near local restaurants such as Tate’s Place and Depot Hot Dogs. Guests also have the option to travel 45 miles to Chicago for additional dining options.
Accommodations at Lakeshore Camp Resort are primarily full hookup campsites. There are 12 cabins on the property that are available to rent for convenience and additional space. Alternatively, an RV can be parked and hooked up for an extended family outdoor adventure!
The starting cost for a four-night stay at Lakeshore Camp Resort is approximately $897.
Address: 5300 Old Porter Rd, Portage, IN 46368-1142
Phone: (219) 762-7757
Website: Lakeshore Camp Resort
Booking.com Rating: 8.3
19. Oakwood Resort
The Oakwood Resort is an honorable mention when discussing all-inclusive family resorts in the Chicago area. Nestled in Syracuse, Indiana, this place provides a secluded retreat for those seeking a private getaway with optional access to the nearby city.
The Oakwood Resort is a hidden gem in Northern Indiana. Tucked away just 2 hours from Chicago, this lesser-known area has plenty to offer traveling families.
The resort property features a game room, fitness center, and gift shop, along with a list of outdoor activity options without having to leave the hotel grounds. Some popular activities include kayaking, paddleboarding, and bicycling with equipment provided by the resort.
Restaurants at the Oakwood Resort include The Pier & Back Porch restaurant, serving gourmet local cuisine in an outdoor dining area. There is also a coffee shop and creamery on-site, as well as a unique igloo dining experience.
Accommodations at the Oakwood Resort include several types of guests rooms. They range in size from standard to premium rooms and suites. Lake homes are also available to rent on the property for families seeking additional space.
The starting cost for a four-night stay at Oakwood Resort is approximately $1,234.
Address: 702 E Lake View Rd, Syracuse, IN 46567-8414
Phone: (574) 457-7100
Website: Oakwood Resort
Booking.com Rating: 8.5