Best & Cheap Family Friendly Vacations in Chicago, IL

Compare family friendly vacation accommodation, From $36/night

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Best & Cheap Family Friendly Vacations in Chicago, IL: Top Deals

Chicago Marriott at Medical District/UIC
Hotel
Chicago Marriott at Medical District/UIC
4.0 (670 reviews)
This Chicago Marriott at Medical District/UIC is a pet-friendly hotel located near the University of Illinois at Chicago. Popular restaurants and activities in the area include The Winchester, a craft beer bar and restaurant offering American cuisine; the National Museum of Mexican Art; and the West Side Park Trail, a scenic trail ideal for running or biking.
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$224.1 /night
Royal Sonesta Chicago Downtown
Hotel
Royal Sonesta Chicago Downtown
This Hotel, Royal Sonesta Chicago Downtown, is located in the heart of downtown Chicago and allows pets. It offers easy access to popular nearby attractions such as The Bean at Millennium Park, Chicago Riverwalk, Navy Pier, Shedd Aquarium, Adler Planetarium, and Field Museum of Natural History. Popular restaurants within walking distance include Lou Malnati's Pizzeria, Giordano's Pizza, Portillo's Hot Dogs, and The Gage Gastropub. There are also plenty of trails and outdoor activities nearby, including Lakefront Trail, Grant Park, Lincoln Park Zoo, and Buckingham Fountain.
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$249 /night
Courtyard Chicago Downtown/River North
Hotel
Courtyard Chicago Downtown/River North
This Hotel, Courtyard Chicago Downtown/River North, is located in the heart of downtown Chicago and allows pets. It's nearby popular attractions include the Navy Pier, Magnificent Mile Shopping District, Millennium Park, and The Art Institute of Chicago. There are also many restaurants and cafes nearby such as Giordano's Pizza, Lou Malnati's Pizzeria, and Heaven on Seven. For those looking for outdoor activities, there are several trails within walking distance, including The Lakefront Trail and The 606 Bloomingdale Trail.
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$174 /night
3B/2.5BA Skyline Glass Penthouse | Breathtaking Views, Indoor Pool, & Gym by ENV
Apartment · 8 Guests · 2 Bedrooms
3B/2.5BA Skyline Glass Penthouse | Breathtaking Views, Indoor Pool, & Gym by ENV
4.7 (27 reviews)
This Apartment is located in Chicago, IL and offers breathtaking views from a 3 bedroom/2.5 bathroom glass penthouse. The building also features an indoor pool and gym for guests to enjoy. Popular nearby restaurants include Public House, Mac's Wood Grilled, and Yuzu Sushi & Robata. For outdoor activities, visitors can explore the Lakefront Trail along Lake Michigan or take a stroll through Millennium Park. Guests can bring their furry friends too as pets are allowed.
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$564 /night*
Waldorf Astoria Chicago Hotel
Hotel
Waldorf Astoria Chicago Hotel
4.4 (294 reviews)
This luxurious 5-star hotel, the Waldorf Astoria Chicago Hotel, is located in the heart of downtown Chicago. It's within walking distance to some of the city's top attractions such as Millennium Park and the Magnificent Mile. Nearby popular restaurants include Gibson's Bar & Steakhouse, Girl & The Goat, and Nico Osteria. Other nearby activities include shopping at Water Tower Place, exploring the Lakefront Trail along Lake Michigan, and visiting the Shedd Aquarium. Pets are allowed.
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$461 /night
Millennium Knickerbocker Chicago
Hotel
Millennium Knickerbocker Chicago
4.0 (3439 reviews)
This luxurious Hotel is located in the heart of downtown Chicago, close to some popular attractions such as Navy Pier, Millennium Park, and The Magnificent Mile. Nearby restaurants include Gibsons Bar & Steakhouse, Lou Malnati's Pizzeria, and Wildfire. There are also plenty of activities nearby like attending a show at the Theater on the Lake, exploring the city by bike with Bike and Roll Chicago, or taking a relaxing walk along the nearby Riverwalk.
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$112 /night
Wonderful Lincoln Park Rowhouse - perfect for groups, reunions and kids.
Guest Suite · 2 Guests · 6 Bedrooms
Wonderful Lincoln Park Rowhouse - perfect for groups, reunions and kids.
5.0 (65 reviews)
This Guest Suite is located in the beloved Lincoln Park neighborhood of Chicago, providing guests with easy access to a variety of popular restaurants, activities, and trails. Nearby eateries include The Little Goat Diner, The Mindy's Hot Chocolate, and Au Cheval. Guests can also explore the nearby nature trails at North Avenue Beach or visit the iconic Lincoln Park Zoo. With its perfect location for groups, reunions, and kids, this Guest Suite is an ideal destination for all types of travelers.
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$1055 /night*
2B/2BA Executive Glass Apt | Balcony, Rooftop Pool & Gym by ENVITAE | PAID IN/OU
Guest Suite · 2 Guests · 3 Bedrooms
2B/2BA Executive Glass Apt | Balcony, Rooftop Pool & Gym by ENVITAE | PAID IN/OU
3.9 (8 reviews)
This Guest Suite is a 2 bedroom and 2 bathroom executive glass apartment located in the heart of downtown Chicago. It offers a balcony, rooftop pool, and gym access provided by ENVITAE. The suite is situated close to popular restaurants like Wildberry Pancakes & Cafe, Girl & The Goat, and Lou Malnati's Pizzeria; exciting activities like the Navy Pier, Millennium Park, and Shedd Aquarium; as well as scenic trails like the Lakefront Trail and Riverwalk.
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$317 /night*
East Village Flat (COVERED ATTACHED GARAGE)
Guest Suite · 2 Guests · 5 Bedrooms
East Village Flat (COVERED ATTACHED GARAGE)
This Guest Suite is located in the East Village Flat of Chicago, and offers an attached garage for parking. Nearby popular restaurants include The Emporium, Lao Sze Chuan, and El Nuevo Mexicano. Popular activities nearby include visiting Navy Pier, exploring Millennium Park, and shopping at The Shops at North Bridge. For outdoor fun, visitors can explore the Lakefront Trail or Riverwalk. With its convenient location and pet-friendly policy, this Guest Suite is perfect for a couple looking to explore the Windy City.
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$1336 /night*
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Which Price Range Is Considered As A Good Deal in Chicago, IL Area?
Vacation Apartment & House Rental Price Information in Chicago, IL
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The graph shows the percentages of vacation homes in each price bucket. Chicago has the largest percentage (27.59%) of homes in $100 - $150 price range.
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How Many Accommodations Are Pets Allowed in Chicago, IL?
Pets Allowed vs Not Allowed in Chicago, IL
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17.57% of vacation homes in Chicago are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
What are some family-friendly restaurants near Chicago, IL?
Family-Friendly Restaurants in Chicago, IL
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Chicago, IL offers a variety of family-friendly restaurants. From classic American fare to Mexican and Mediterranean cuisines, there's something for everyone. Here are three great places to check out in the area.

  • Gibsons Bar & Steakhouse: This upscale steakhouse serves USDA prime steaks and seafood with an extensive wine list. The restaurant also features an outdoor patio where you can enjoy your meal al fresco.
  • Big Star: This popular spot serves up tacos, margaritas, and live music in a laidback atmosphere. Big Star is perfect for a fun night out with the family.
  • Yolk: This lively breakfast joint has something for everyone. Enjoy classic omelettes, pancakes, French toast, and more in a bright and cheery atmosphere.
What are some family-friendly activities near Chicago, IL?
Family-Friendly Activities in Chicago, IL
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Chicago, IL is home to plenty of fun activities for families. Whether you're looking for indoor or outdoor activities, there's something for everyone. Here are three great ideas to get you started.

  • Navy Pier: This iconic pier features rides, shows, and attractions for all ages. From the Ferris wheel to the Chicago Shakespeare Theater, Navy Pier is the perfect destination for a memorable day out.
  • The Magnificent Mile: Explore this stretch of Michigan Avenue to find unique shops and restaurants. Take a stroll along the riverfront, visit the nearby parks, or catch a show at one of the local theaters.
  • Museum of Science and Industry: This museum is the largest of its kind in the Western Hemisphere. It features interactive exhibits, tours, and programs that will keep the whole family entertained.
Which Airports Should I Choose To Get To Chicago, IL?
Suggested Airports in Chicago, IL
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