Chicago Vacation Rentals with pool

Robert Blomfield
1 year ago

Are you in a hurry?

Here is a quick list of hotels in Chicago, selected based on their rating

Name of hotel Accommodation Rating Price, $
3Br Premium Executive Penthouse W/ Pool & Parking Apartment

7.4 / 10

(9 Reviews)

From 836$
Relaxed Hp 1Br With Fast Transit To Uchicago & Dt By Zencity

6.5 / 10

(2 Reviews)

From 218$
Envitae 3Br Spacious Lux Skyview Of Navy Pier Apartment

7.6 / 10

(5 Reviews)

From 647$
3Br Stunning Spacious Sky Loft Indoor Pool, Parking & Incredible Views

8.4 / 10

(10 Reviews)

From 874$
Uptown Gem Apartment

9.2 / 10

(9 Reviews)

From 362$

To enjoy a swimming pool on site, rent Global Luxury Suites In Downtown or 3Br Premium Executive Penthouse W/ Pool & Parking. Find other popular properties featuring a pool here.

Table of contents

3Br Premium Executive Penthouse W/ Pool & Parking Apartment Relaxed Hp 1Br With Fast Transit To Uchicago & Dt By Zencity Envitae 3Br Spacious Lux Skyview Of Navy Pier Apartment 3Br Stunning Spacious Sky Loft Indoor Pool, Parking & Incredible Views Uptown Gem Apartment Envitae 2Br Vibrant High-Rise Penthouse Apartment Envitae 3Br Luxury Corner Loft With Navy Pier Views Apartment 2B,2Ba Luxury Apartment Balcony,Wi-Fi, Paid In&Out Parking In Bldg Captivating Apartment With Pier Views, Pool And Gym 3Br Sophisticated Sky Suite With Incredible Views

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7.4
Good
9 Reviews

3Br Premium Executive Penthouse W/ Pool & Parking Apartment

📍 North Harbor Tower, 175 North Harbor Drive

From 836$

The premier natural-history Field Museum is located 1.8 km from the venue. The apartment is a 10-minute walk from the beach. Seven Bar and Restaurant as a dining option is approximately 200 metres away. Take a few minutes' cab ride to see Shedd Aquarium.

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6.5
Good
2 Reviews

Relaxed Hp 1Br With Fast Transit To Uchicago & Dt By Zencity

From 218$

The apartment offers access to Promontory Point Park, situated nearby. The beaches of Chicago are about 400 metres away. Whole Foods Market and McDonald's are 5 minutes’ walk away. The Sprawling hands-on Museum of Science and Industry is also a short ride away.

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Popular Hotels with pool destinations

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7.6
Very good
5 Reviews

Envitae 3Br Spacious Lux Skyview Of Navy Pier Apartment

📍 West Huron Street

From 647$

Skydeck Chicago can be reached by car in a couple of minutes, while Arts Club of Chicago is right by the property. The city centre of Chicago is a 30-minute walk away. American food is served in Current within 150 metres from the apartment. The half-mile-long Navy Pier is set nearby.

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8.4
Very good
10 Reviews

3Br Stunning Spacious Sky Loft Indoor Pool, Parking & Incredible Views

📍 111111 West Wacker Drive

From 874$

The venue is nestled in Chicago Loop district of Chicago, which is 15 minutes' walk to the city centre. The skyscraper 360 Chicago Observation Deck is at a distance of 20 minutes' walk and State/Lake metro station is around 300 metres away. Guests can enjoy American meals in Ace Bounce, which is about 50 metres away. Landmarks not too far from the apartment include Chicago Riverwalk and The Rookery Building.

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9.2
Excellent
9 Reviews

Uptown Gem Apartment

📍 1020 West Lawrence Avenue #522

From 362$

The newly developed Gallagher Way Plaza can be reached by car in a couple of minutes, while Saint Thomas of Canterbury Roman Catholic Church is right by the accommodation. 3 Squares Diner, Dib Sushi Bar and Thai Cuisine serving delectable dishes are approximately 100 metres away.

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Hotels in Chicago

Airport nearby ✈️ Midway International, Chicago O'Hare International
Average Price 💰 312$
Hotels in Chicago 🏨 1065
Hotel Reviews ⭐ 29055
Landmarks nearby 📍 Chicago Children's Museum, Money Museum at the Federal Reserve Bank, United Center, Andersonville, The Magnificent Mile
Top Hotel for couples 💑 3Br Premium Executive Penthouse W/ Pool & Parking Apartment
Top Service Hotel 🛁 Relaxed Hp 1Br With Fast Transit To Uchicago & Dt By Zencity
Family Hotel 👪 Envitae 3Br Spacious Lux Skyview Of Navy Pier Apartment

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7.2
Good
4 Reviews

Envitae 2Br Vibrant High-Rise Penthouse Apartment

📍 420 East Ohio Street

From 909$

This accommodation lies within 30 minutes' walk of the centre of Chicago. The public Cloud Gate Sculpture, a tourist attraction, is a 20-minute walk from the apartment. Guests will enjoy American cuisine of Yolk - Streeterville, which is about 150 metres away. Take a few minutes' cab ride to see Skydeck Chicago.

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10
Excellent
3 Reviews

Envitae 3Br Luxury Corner Loft With Navy Pier Views Apartment

📍 West Lake Street

From 652$

The accommodation is 25 minutes’ walk from the - art Shedd Indoor Aquarium. The city centre is 20 minutes' walk from the apartment. Serving Italian meals, Giordano's lies 50 metres from the property. You can get to the skyscraper 360 Chicago Observation Deck in a couple of minutes by car.

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6.8
Good
5 Reviews

2B,2Ba Luxury Apartment Balcony,Wi-Fi, Paid In&Out Parking In Bldg

📍 220 West Illinois Street

From 457$

Due to its location in the centre of Chicago is the super - tall skyscraper "Willis Tower" within a short car ride, while The Richard H. Driehaus Decorative Arts Museum is easily reachable nearby. A 20-minute walk will take you to the city centre. The nearest seafood restaurant is 200 metres from the apartment. Chicago-style pizza is not far from the property.

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9
Excellent
3 Reviews

Captivating Apartment With Pier Views, Pool And Gym

📍 420 East Ohio Street

From 674$

The venue is located in Chicago, a 25-minute walk from its centre. The nearest beach is 900 metres away. Guests can dine in Drunken Bean Cafe within 100 metres of the apartment. The tall skyscraper "Willis Tower" is also a short ride away.

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3Br Sophisticated Sky Suite With Incredible Views

📍 North Harbor Tower, 175 North Harbor Drive

From 1299$

This accommodation is located in the centre of Chicago. Guests can find the Oak Magnificent Mile Street in the area. Drunken Bean Cafe is within 200 metres. The tall skyscraper "Willis Tower" is a short taxi ride away.

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3
Good
3 Reviews

Relaxed Hp 1Br With Fast Transit To Uchicago & Dt By Zencity

From 208$

The venue is located in Hyde Park district of Chicago, about 350 metres from a beach. The property is set within a 10-minute ride from Guaranteed Rate Field. The brew pub Jolly Pumpkin Pizzeria and Brewery is around 5 minutes’ walk away. The apartment enjoys proximity to Promontory Point Park.

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6
Good
1 Reviews

2B 2Ba Executive Glass Apartment With Balcony & Wi-Fi

📍 West Illinois Street 220

From 458$

Due to its location in the heart of Chicago is The Chicago Theatre within a short car ride, while Chicago Vietnam Veterans Memorial is easily reachable nearby. The accommodation lies in Downtown Chicago district. Guests may find the bar Ironside Bar & Galley within 200 metres from the apartment. Chicago-style pizza is also nearby.

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8.7
Excellent
4 Reviews

3Br Exquisite Lake View Loft W/ Parking In Building

📍 North Harbor Tower, 175 North Harbor Drive

From 783$

Skydeck Chicago and CIBC Theatre are respectively within 2.1 km and 1.3 km of the venue. The property is a 10-minute walk from the beach. For drinks and meals there are Seven Bar and Restaurant, and Ming Hin Cuisine nearby, about 250 metres away. The apartment is nestled within a short taxi ride from 360 Chicago Observation Deck.

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9.8
Excellent
5 Reviews

Ultimate 3Br Luxury Suite Near Navy Pier With Gym & Pool By Envitae

📍 North Saint Clair Street

From 461$

The apartment is located in Chicago, a 30-minute walk from its centre. The beach is 350 metres away. Offering American meals, Yolk - Streeterville is around 150 metres away. You can get to Museums in the Park in a couple of minutes by car.

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8
Very good
14 Reviews

3B/3B Skyloft With Navy Pier View Gym & Pool By Envitae Apartment

📍 420 East Ohio Street

From 1450$

The accommodation is placed within a 10-minute drive from the premier natural-history Field Museum. A beach is 400 metres away. L'Aventino Forno Romano as a dining choice is 150 metres away. Take a few minutes' cab ride to see Millennium Public Park.

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2Br Navy Pier Loft With Pool, Gym & Views By Envitae Apartment

📍 420 East Ohio Street

From 275$

The accommodation is 10 minutes’ walk from the half - mile - long Navy Pier. The venue can be found in Magnificent Mile district, within 30 minutes' walk from the city centre. L'Aventino Forno Romano and Cafe Descartes can be reached within a 5-minute walk from the property. Millennium Public Park is a short taxi ride away.

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6.7
Good
3 Reviews

2B 2Ba Sophisticated Luxury Apartment With Balcony, Wi-Fi, Paid Parking On Premises

📍 West Illinois Street 220

From 457$

Due to its location in the very heart of Chicago is the super-tall skyscraper "Willis Tower" within a short car ride, while Blue Chicago Orchestra is easily reachable nearby. By car, it is a 10-minute journey to the half-mile-long Navy Pier. The seafood restaurant GT Fish & Oyster is around 200 metres away.

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9.3
Excellent
22 Reviews

2Br Elegant Premium Suite With Balcony & Sweeping City Views

📍 West Illinois Street 220

From 458$

Due to its location in the centre of Chicago is the public Cloud Gate Sculpture within a short car ride, while Chicago Vietnam Veterans Memorial is easily reachable nearby. A 20-minute walk will take you to the city centre. Gene & Georgetti and Yu Choy can be found within 150 metres of 2Br Elegant Premium Suite With Gym & Pool By Envitae apartment. The venue is set a few steps from Chicago-style pizza.

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10
Excellent
1 Reviews

1Br Spacious Luxury Suite With Balcony, Wi-Fi & Paid In And Out Parking

📍 West Illinois Street 220

From 221$

Guests can visit the skyscraper 360 Chicago Observation Deck, 1.7 km away or the free Lincoln Park Zoo, 3.2 km from the accommodation. The apartment can be found in Downtown Chicago district, within 20 minutes' walk from the city centre. Gene & Georgetti and Yu Choy are situated a 5-minute walk away. The downtown Museum Of Contemporary Art Chicago can be reached in a few minutes by car.

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7
Good
3 Reviews

1Br Luxury Apartment With Private Office, Terrace, & Wi-Fi

📍 West Illinois Street 220

From 424$

The accommodation is located in Downtown Chicago district, about 5 minutes' drive from the public art Cloud Gate Sculpture. Guests can walk to the super-tall skyscraper "Willis Tower" in 19 minutes. The restaurant Veggie Grill can be reached after a 5-minute walk. 1Br Luxury Apartment With Private Office, Terrace, Gym & Pool is within a short distance of Chicago-style pizza.

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9
Excellent
4 Reviews

2Br Executive Suite With Fast Wi-Fi

📍 West Illinois Street 220

From 458$

Due to the location Downtown Chicago district, landmarks including Chicago Vietnam Veterans Memorial are easy to reach. The premier natural-history Field Museum is 2.6 km away from the accommodation. GT Fish & Oyster, which is not far from 2Br Executive Suite With Pool, Gym & Fast Wi-Fi By Envitae apartment, serves American and international cuisine. Take a few minutes' cab ride to see the downtown Museum Of Contemporary Art Chicago.

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Streeterville Furnished Apartments

📍 514 North Peshtigo Court

From 111$

Major Chicago sights, such as the half-mile-long Navy Pier and the Oak Magnificent Mile Street are located not far away. The city centre is just 3 km away and Midway International airport is 20 km from the venue. Guests can dine at café, which is about 50 metres away. The Art Institute of Chicago is also a short ride away.

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Chicago Vacation Rentals with pool FAQ
What are the top-rated holiday rentals in Magnificent Mile district?
Our guests usually stay in high-rated holiday houses in such districts as — Lakeview, West Town and Hyde Park.
What are the finest Chicago holiday rentals to stay with pets?
Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok is the best pet-friendly weekend home in Chicago, in which prices start from 399US$.
What budget holiday rentals in Chicago would you recommend?
According to guest ranking above 8.4/10, the best budget holiday accommodation is Homan Square.
How much does a 3-bedroom holiday house cost for a week?
For a 3-bedroom holiday rental in Chicago you might spend about 1008US$. Check this popular option — The Avondale Guesthouse.
What are the most popular Chicago holiday rentals near a beach?
If you are searching for a beach villa, Old Town-Gold Coast Amazing 3 Bedroom Home/ Free Parking/ Breakfast/ Backyard/ Walk Everywhere/ Pets Ok is a great option to consider.
What are the top holiday rentals with pools in Chicago?
To enjoy an onsite pool, rent Global Luxury Suites In Downtown or 3Br Premium Executive Penthouse W/ Pool & Parking. Check more popular holiday accommodations here.
What are the best holiday rentals with free wifi in Chicago?
Pittsfield Apartments And Suites and 5430 Happy Home are the best holiday accommodations providing free wifi.

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