9 best Airbnbs with pools near Chicago well worth a dip

A sandy backyard area thronged by tall beach grass means you’ll have no trouble envisioning you’re waterside at this stately Michigan home, which also features a putting green and a hot tub on its premises. Bonus: the house is only two blocks from Lake Michigan’s shore if you feel like switching up your swimming routine.

Rooms? Five bedrooms. Sleeps 14 guests. 

The mood? An old charmer. 

Location perks? The heated in-ground pool is accompanied by a hot tub, gas grill and a large outdoor dining area. 

Budget range? A moderately-priced group trip. 

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.

Okay, we know it's giving Flintstones, but this rustic Airbnb has – in our opinion – the coolest swimming pool/pond combination within easy distance from Chicago. What's more, this is the ideal home for a large family looking for adventure. This epic home has seven bedrooms with a total of 15 beds – yes, 15 – and 2.5 bathrooms. Aside from the uber-cool rock-pool-style pond, there's a full basketball court, volleyball, pickleball, a trampoline, an outdoor kitchen, and a grill – oh, and there's a hot tub if that's more your vibe. Dive in.

Rooms? Seven bedrooms. Sleeps 16 or more.

The mood? A nostalgic family adventure.

Location perks? Looking for a homely vibe? This one is situated at the end of a cul de sac so it feels safe and secluded.

Budget range? Surprisingly affordable when you spread 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.

This beautiful lakeside house can sleep up to 20 guests. So assemble your nearest and dearest, and head off for a long weekend or summer vacation to remember. Along with the heated private pool, visitors can while away the hours on the fishing pier or try out a range of watersports on the lake. It’s also a pretty sweet spot to simply kick back and relax in.

Rooms? Seven bedrooms. Sleeps 16 guests or more. 
The mood? Country chic. 
Location perks? Walking distance to Twin Lakes – kayaks, canoes and paddle boards are available for rental. 
Budget range? An exceptional location at affordable rates. 

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. 

It’s not often you can apply the word "tropical" to something in southern Michigan, but this place fits the bill: A saltwater pool, sandy backyard, hammocks, colorful blooming flowers, and even a tiki bar (complete with multi-flavored vodkas and IPA on tap) work to create an almost island-like feel.

Rooms? Four bedrooms. Sleeps eight guests. 

The mood? A slice of Malibu.

Location perks? A stone's throw from downtown and Lake Michigan where you can enjoy bike tours, hiking, and of course, getting out on the water.

Budget range? Moderately priced for four nights. 

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.
 
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.