House holiday rentals in Grant Park, Chicago

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Popular amenities for Grant Park, Chicago house rentals

House rentals with a pool

Top Guest favourite
Home in Schererville
4.95 out of 5 average rating, 56 reviews

Cozy house in Schererville

AnyaRating, 5 stars3 weeks ago
Very well thought through place for every detail, with a mix of 70s wood style and some higher tech upgrades like the main bathroom mirror with light and anti fog, or sensor lights. Kate was very responsive and accommodating for the 1 baby & 1 toddler we asked for. The place was stocked with all necessary items especially in the kitchen with appliances and cutlery, coffee, tea. There were 2 hairdryers, nice shampoo and conditioner, shower gel.
Guest favourite
Home in Munster
5 out of 5 average rating, 11 reviews

Munster hide away

ChristopherRating, 5 stars5 months ago
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.
Superhost
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month ago
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!
Guest favourite
Home in Bloomingdale
4.92 out of 5 average rating, 52 reviews

Now Open: Heated Pool with Entire House

AmyRating, 5 starstoday
Really great place to stay, super responsive host! The pool was pretty great and so was the hot tub! Great location too, lots of stores, restaurants around, and parks like the Busse Woods (it’s huge and lots of walking paths)!
Superhost
Home in Miller
4.83 out of 5 average rating, 36 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars6 months ago
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars1 week ago
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!
Superhost
Home in Lincoln Park
4.88 out of 5 average rating, 56 reviews

Luxury Loft with Private Pool and Movie Theater

RyanRating, 5 stars1 week ago
Damani was a great host, really responsive and easy to communicate with! The house was exactly as advertised and really nice! The pool was great!
Top Guest favourite
Home in Crown Point
5 out of 5 average rating, 54 reviews

Little Pink House Downtown

ErikaRating, 5 stars8 months ago
The Little Pink House greatly exceeded our expectations. Suzanna was a wonderful host who went above and beyond to make sure our stay went smoothly. We were in town for a wedding and had an infant with us and the provided amenities made it feel like home. We would absolutely love to stay again if we get the chance.

Weekly house rentals

Top Guest favourite
Home in Garfield Ridge
4.95 out of 5 average rating, 61 reviews

Chicago Home (1st floor) by Midway near Downtown

DelaneyRating, 5 stars5 days ago
My friends and I had a great time staying at Joanna’s place! It was super clean, the neighborhood was nice, and there were lots of stores and restaurants around the area too! We would definitely stay again :)
Guest favourite
Home in Chicago
4.93 out of 5 average rating, 44 reviews

Floresitas Oasis, your home in Chicago

Kawina RochelleRating, 5 stars2 days ago
Lizbeth was an amazing host. She’s responsive and attentive. The place was exceptional clean and had an amazing smell. I was there to celebrate my birthday and was pleasantly surprised upon entry when I was greeted with a personalized birthday message, fresh flowers and a bottle of wine. Anytime I reached out to Lizbeth, she responded expeditiously. Again, very attentive. My husband and I will definitely stay at her beautiful Oasis again. We felt comfortable and completely safe. Everything we wanted to do was a quick drive from the location. If you’re considering staying at her home, you will not regret it. If I could give more than 5 stars, I would. Thanks Lizbeth for being an incredible host Until the next time…
Guest favourite
Home in Chinatown
4.93 out of 5 average rating, 27 reviews

3 bd/ 2ba with Free Parking Spot by McCormick

AadhyaRating, 5 stars1 week ago
Had an amazing experience!! Host was very quick with responding on text if there were any issues too.
Top Guest favourite
Home in Miller
5 out of 5 average rating, 28 reviews

5 min walk to the beach

MariahRating, 5 stars1 day ago
Derek is professional and friendly. He was flexible with us in a way that helped our travels a great deal. I appreciate his tech savvy home and will likely revisit the location. It’s about an 8 min walk to a clean beach where everyone is kind.
Guest favourite
Home in Chicago
4.95 out of 5 average rating, 22 reviews

Big house in the BEST Location!

JodiRating, 5 stars2 days ago
The house is lovely! Better than the pictures, just as all of the reviews say. The showers are incredible. The master bathroom is a dream. We had everything we needed & more. We don’t have a single complaint. We definitely plan on booking here again.
Guest favourite
Home in Washington Park
4.95 out of 5 average rating, 57 reviews

Historic Hyde Park Gray stone (upper)

FadiRating, 5 stars2 weeks ago
Absolutely stellar stay! Kymi’s Airbnb in Chicago was everything we hoped for and more during our time at ASCO. The home was beautifully decorated, exceptionally comfortable, and stocked with everything we needed. My family felt incredibly safe and at ease the entire time. Kymi herself was a dream host—warm, responsive, and genuinely hospitable. She graciously allowed us to extend our stay and have a late checkout, all without hesitation or hassle. Her kindness and attentiveness made the experience even more special. I highly encourage anyone visiting Chicago to stay at her amazing home—you won’t regret it!
Superhost
Home in Chicago
4.9 out of 5 average rating, 29 reviews

Executive Contemporary Duplex

KaylaRating, 5 stars5 days ago
Perfect location! Not far from the best things to do in the city. The neighborhood is quiet and safe. I would highly recommend!
Superhost
Home in Gary
4.91 out of 5 average rating, 79 reviews

Laurna Dune

EusebiaRating, 5 stars2 weeks ago
We had a wonderful stay at this property, it truly felt like a home away from home. The entire place was exceptionally clean, and the kitchen and dining area were spacious and easy to move around in. Both bedrooms were spotless, and the mattresses were incredibly comfortable. If you’re looking for a quiet, private place to stay, this is the perfect choice. I would definitely stay here again! 😊

Private house rentals

Superhost
Home in West Lawn
4.92 out of 5 average rating, 48 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

EhjayRating, 5 stars2 weeks ago
Very nice space to bring friends over
Guest favourite
Home in Chicago
5 out of 5 average rating, 10 reviews

The Modern Muse of Chicago! Close to everything!

VictoriaRating, 5 stars1 week ago
Jasna was an amazing host! The house was absolutely spectacular—truly even better than the photos. Every room felt thoughtfully designed and full of warmth, making it feel just like home. We had all the amenities we needed, which made our stay super comfortable and stress-free. It was the perfect setting for a special girls’ trip with my mom and sister. The neighborhood was peaceful and beautiful, adding to the relaxing vibe. We’ll definitely be back! Thank you again for everything, Jasna!
Superhost
Home in Bronzeville
4.96 out of 5 average rating, 49 reviews

3bd/3ba Bronzeville Beauty

BrittanyRating, 5 stars2 months ago
The hosts’ of this property were great and accommodating. They catered to our altered schedule and compromised on a request of ours. We will definitely stay here again.
Top Guest favourite
Home in Northbrook
4.97 out of 5 average rating, 73 reviews

*King bed *Outdoor Living *Sought-After Area

TylerRating, 5 stars2 weeks ago
Beautiful home, clean and worked perfect for our family. Elisabeth always responded quickly and it was a seamless check in and check out process.
Superhost
Home in Chicago
4.71 out of 5 average rating, 21 reviews

Lux_Home Chicago 8 mins Downtown

StephenRating, 5 stars2 days ago
Everything was exactly as pictured, and the space was clean and comfortable. The location is quiet, which made for a peaceful stay. Evan was an excellent host—accommodating, kind, and flexible. He responded promptly to any questions and made the experience seamless. Would definitely stay again!
Superhost
Home in Roseland
4.89 out of 5 average rating, 73 reviews

Experience Chicago from Our 3-Story Retreat

SylviaRating, 5 stars1 week ago
The home is lovely we are seniors so the steps were a little bit tricky for us. I thought it was a bit closer to town but that was my mistake but the home is very relaxing and perfect for a large group or family I would highly recommend this home and our host was exceptional
Top Guest favourite
Home in Brookfield
4.97 out of 5 average rating, 29 reviews

Cozy Home in Brookfield

TomRating, 5 stars1 week ago
Juliana was a great host and we felt right at home. She was very friendly and helpful. The place was outstanding and the fenced in huge backyard was awesome. Our dogs loved it. I would highly recommend this place to anyone visiting the area.
Top Guest favourite
Home in Logan Square
5 out of 5 average rating, 26 reviews

Sunny Historic Cottage on the Park

MichelleRating, 5 stars6 months ago
We loved Megan’s place! It’s adorably decorated and very cozy. We felt at home during our stay. The beds were comfortable and the kitchen was great for cooking dinner one night. Checking in and out was really simple. You’re not immediately by the train, but it’s a quiet safe neighborhood and there’s a little park across the street and a cute coffee shop a short walk from the house. As was clearly indicated by the hosts, it’s notably warmer upstairs than it is downstairs (we stayed in November) but it wasn’t a real issue. Would happily stay here again.

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