Home Family Vacation Ideas 8 Airbnb Rentals for Chicago Families with Epic Pools by Maria ChambersJuly 11, 2022 Airbnb Search more like this bike trailsbocce courtsfarm lifegame roomgolf coursehome cookedmovie nightpinball machinesping pongquality timeroad tripsvacation rentalsairbnbsand beaches Advertisement Trending Now Viral & Trending School’s Cell Phone Policy Goes Viral after Mom Refuses to Comply: ‘Nope’ News California Becomes 1st State to Provide Free Meals to Public School Kids News CDC’s New COVID Guidelines: Kids Can Stay in Class If Exposed News Nanny Job Listing Goes Viral Because It’s Bonkers News The ‘Sweet Magnolias’ Cast Is Posting Sneak Peeks of Season 3 on Instagram Advertisement No need to book family vacations to far-away destinations this summer, because this is the time of year we live for as Chicagoans. The temps are perfection, the activities are aplenty and the landscape is gorgeous. If you’d like an escape from your own four walls, turn to Airbnb. From high-rises in Chicago to mini road trips to farmhouses with chickens, you can snag an Airbnb rental that features a pool and fun family-focused amenities. Airbnb 137-Year-Old Farmhouse | Lake Forest This updated 5-bedroom farm home in Lake Forest is a great option for extended families looking to spend quality time together. It’s a stone’s throw from a public golf course, downtown Lake Forest is just a mile down the road and a romp in the sand at the beach is just two miles away. Sleeps: 9Cost: $700/nightOnline: airbnb.com Airbnb Farmesque with a Splash of Modern | New Buffalo This 5-bedroom stunner built in 2019 will have you feeling like you rolled back time with trough sinks, a claw foot tub, distressed floors and cedar beams, but has modern touches and amenities throughout. Galien River Marsh is across the street and there are several bikes on property to take a cruise. This is great because the downtown area is just 3 blocks away and you’re 6 blocks from the beach. The cottages have a pool within the community for renters to take a plunge and there’s a fully-stocked firepit in the backyard. Sleeps: 14Cost: $632/nightOnline: airbnb.com Airbnb 1 Pond Place | Union Pier Cozy in with the family in this 2-bedroom cottage located on a quiet cul-de-sac next to a charming pond. Stargaze pond-side with fire blazing or head to the clubhouse for ping pong, foosball and a heated pool. Sleeps: 6Cost: $335/nightOnline: airbnb.com Airbnb A Fisherman’s Dream Retreat | Milwaukee Step right outside your back door and fish the day away, chill on the sand beach at the fishing pond or hop on a paddleboard. If you prefer pool to pond, there’s also an in-ground pool and hot tub. End the night as a family relaxing in the game room.Sleeps: 16Cost: $550/nightOnline: airbnb.com Airbnb Pool with a View | River North Plan a staycation in River North at this 2 bedroom condo with breathtaking views and amenities. The pool features a hot tub, cabanas, chaise lounges and access to grill stations and fire pits. Bond with the family on the bocce court or show the kids your skills in the arcade that includes pinball machines and skeeball.Sleeps: 4Cost: $814/nightOnline: airbnb.com Airbnb Modern Spanish Abode | Plainfield Warning: You’ll never want to leave this modern, luxurious escape. Swan dive into the backyard pool, chill on the rooftop balcony equipped with heat lamps and take advantage of the chef’s kitchen to whip up a home-cooked meal. Retire to the theater room for a memorable family movie night!Sleeps: 8Cost: $570/nightOnline: airbnb.com Airbnb Stately Manor | Wayne This one is a bit of a splurge, but with 7 bedrooms, there’s enough space to bring along multiple families! This modern farmhouse sits on an acre of land and the pool ranges in depth from 3′ to 12′ and includes a slide and diving board. Also. . . there are chickens, which will absolutely delight the kids who like a bit of the farm life.Sleeps: 16Cost: $1,999/nightOnline: airbnb.com Airbnb Sweet Ranch | Glenview This 4-bedroom ranch in Glen Oak Acres puts you within minutes of Wagner Farm, bike trails, walking paths and downtown Northfield, Glenview and The Glen. The outdoor living space includes an in-ground heated pool, grill, pergola and firepit.Sleeps: 7Cost: $371/nightOnline: airbnb.com RELATED STORIESThe Current 411 on Your Favorite Summer Street FestsCool Airbnb Rentals for Chicago FamiliesHave a Sleepover with Mother Nature: Best Glamping Spots Close-Ish to Chicago Click to share on Facebook (Opens in new window)Click to share on Twitter (Opens in new window)Click to share on Pinterest (Opens in new window)Click to email a link to a friend (Opens in new window)Click to share on Copy (Opens in new window) Search more like this bike trailsbocce courtsfarm lifegame roomgolf coursehome cookedmovie nightpinball machinesping pongquality timeroad tripsvacation rentalsairbnbsand beaches Welcome to our Tinybeans family! Be sure to check your email for new activities, recipes and parenting hacks – and to see if you’ve won! Do you have a dog or cat? 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