8 best Airbnbs with pools near Chicago well worth a dip

Even in the summer, you can’t bank on the weather is great all the time – so sometimes you need an indoor pool too. This swanky lodge in Green Bay has a heated indoor pool that comes with a volleyball net. If you’re not the sporty type, the rental also has a poker table, massage chairs, a videogame corner, and plenty of flat-screen TVs.

Rooms? Six bedrooms. Sleeps 14 guests.

The mood? Contemporary glam.

Location perks? Perched on a hillside, this vacation home not only has gorgeous views, but a backyard, movie theatre, and best of all, the pool stays warm all year round.

Budget range? Top dollar quality time with the fam. 

Big enough for an enormous group of friends or family (up to 15 guests, in fact), this luxury home Airbnb is perfect for your trip away from Chicago. With a huge backyard pool and BBQ area, you can soak up the rays in this Airbnb and you'll never want to leave. Luxurious, modern, and comfortable. 

Rooms? Six bedrooms. Sleeps 15 guests.

The mood? Mini paradise.

Location perks? Set on two private acres of lush greenery–that's more than enough room for hide and seek or a cute picnic.

Budget range? Hefty, but decent when you split the cost.

Fancy a stay in a country estate? Now's your chance. This Chicago Airbnb complete with a stunning outdoor pool has all of your luxury needs covered. From a fully equipped open-plan kitchen and dining area to the well-positioned bedrooms with epic views, it's an ideal getaway for the whole family. The property can sleep up to eight guests comfortably while the manicured garden offers peace and tranquillity – especially if you've brought the kids along.

Rooms? Three bedrooms. Sleeps eight guests.
 
The mood? Dreamy and antique. 

Location perks? Manicured landscapes, walking trails and biking paths. Bellisimo. 

Budget range? Not too shabby for a friend's trip or a family vacay.

On the edge of a forest and about a mile from the scenic beach town of Saugatuck, this ridiculously pretty hideaway boasts not just a magnificent, chaise longue-lined pool and an outdoor shower but its own private basketball court. The pool isn’t open year-round (it closes in October), but the hot tub certainly is.

Rooms? Three bedrooms. Sleeps 10 guests.

The mood? Cozy lodge house vibes. 

Location perks? A peaceful oasis with the coziest well-appointed rooms and private beach access on Silver Lake. 

Budget range? A luxury getaway. 

If you want gorgeous panoramic views all year round, stay at this modern studio situated in River North. Along with river and city views, the property dazzles with an outdoor pool area on the rooftop that looks out over the city. Inside you'll find a very comfy abode with bright interiors and a boho-inspired deco theme. Looking for a long-haul stay? No problem, you'll have access to the on-site fitness suite, common room, steam room, and sauna when you're in want of a little pampering. Being so close to the action, means there are a handful of bars and restaurants at your disposal along with Magnificent Mile. But if it's too windy out you can also retreat to the indoor pool.

Rooms? One bedroom. Sleeps 2 guests.
 
The mood? A slice of Malibu.

Location perks? All-star amenities including two pools, a gym, a lounge, and more.

Budget range? On the dearer end, but then again, those views.  

What better way to spend a peaceful weekend than in a private villa off the coast of Lake Michigan. This brand new custom built home is your answer to escaping the city for a staycation and swim. The beautiful heated salt water swimming pool is available from May 1st to September 30th, but there's a year-round 8-man hot tub if you're planning a winter trip. The outdoor space is complete with a firepit and BBQ area, along with alfresco seating. Everything inside is shiny and modern, from the materials to the furniture. Easy to keep clean, cozy and spacious – what more could you ask for? They haven't held back on the fixtures or amenities, with a full chef's kitchen, spa-like bath and custom designed bunk beds. Take advantage of the location by exploring the woodland trails, 5-acre lake, apple orchard and picture-perfect ravine. 

Rooms? Four bedrooms. Sleeps 10 guests. 

The mood? Luxury retreat. 

Location perks? You're 15 minutes away from the coastal town of St. Joseph and South Haven. You're also 5 minutes from the beach and in the heart of the wine country. 

Budget range? A price you can't argue with. 

Get the gang together for a group holiday to this 12-man property in Ottawa that's pretty much an adult funhouse. Let's start with the huge indoor pool: splash around like a big kid, play games and swim laps before soaking in the hot tub. Board games and an Xbox One are available if you don't want the fun to stop once you get out the water. Whether you want to make use of the air fryer, high-end six-burner stove or the BBQ out back, enjoy whatever you've made on the extendable dining table where there's room for everyone. All of the bedrooms and bathrooms are full-size – you'll be spoilt with the amount of space in this house. 

Rooms? Four bedrooms. Sleeps 12 guests. 

The mood? A palace of entertainment. 

Location perks? 10-minute walk from downtown where there's many restaurants, bars, parks and shopping options. 

Budget range? Reasonable!

Benefiting from both a secluded and close-to-the-city location, this family cabin offers peace and quiet while still being nearby entertainment districts. Settle into your own private oasis, as this sits atop acres of land, surrounded by nature and lush forest scenery. Expect ample space to relax, entertain and even get competitive on the pool table. Characterful and cozy, this is the ultimate staycation for adventurous families who also enjoy some quality time indoors. Games, puzzles, yoga mats, pool toys and a BBQ – you name it, this place probably has it. And in the height of summer, the A/C and ceiling fans are lifesavers.

Rooms? Four bedrooms. Sleeps eight guests. 

The mood? Rustic retreat. 

Location perks? 20 minutes away from two ski resorts, a winery and distillery, restaurants and spas. Minutes away from Lake Wisconsin. 

Budget range? Pretty standard.