West Side Holiday Rentals

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Holiday Rentals in West Side

Our top choices for West Side holiday rentals

Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (352)
"Great stay!"
The price is HK$1,318
HK$1,547 total
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (194)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (209)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is HK$1,518
HK$1,782 total
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is HK$5,848
HK$9,672 total
includes taxes & fees
8 Sept - 9 Sept
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Living room

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is HK$1,650
HK$1,937 total
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy Greektown Apartments
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is HK$811
HK$1,688 total
includes taxes & fees
3 Sept - 4 Sept
Stylish 1BR in West Loop
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Terrace/patio

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
9.0 out of 10, Wonderful, (9)
"We got all the help and instructions needed to easily find this clean, well-supplied apartment with lovely outdoor space attached. And with the Pink Line just a few minutes walk and The Loop just 6 stops away, it was the perfect home base for getting to all that Chicago has to offer!"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Iron/ironing board, WiFi, bed sheets

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago
Spacious 3-bedroom apartment near downtown, FREE PARKING
Private kitchen

Spacious 3-bedroom apartment near downtown, FREE PARKING

9.4 out of 10, Exceptional, (3)
"Extremely clean space that was perfect for our group. We didn't spend a lot of time in the home during our stay, but when we did it was fantastic. Only minor gripe would be the upstairs neighbors, they were occasionally quite loud and woke us up a few times in the middle of the night. Would absolutely stay here again, if/when we come back to the area."
The price is HK$569
HK$2,771 total
includes taxes & fees
3 Sept - 4 Sept
Spacious 3-bedroom apartment near downtown, FREE PARKING
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Property grounds

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (52)
"The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (17)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is HK$856
HK$1,572 total
includes taxes & fees
15 Sept - 16 Sept
Ground Floor Studios in Chicago by 747 Lofts
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Outdoor dining

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

10.0 out of 10, Exceptional, (251)
"Well stocked, spacious and beautifully decorated, excellent location, attentive host. We had a great stay!"
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Your Perfect 2BR Home w/ Parking
Fridge, microwave, oven, stovetop

Your Perfect 2BR Home w/ Parking

8.4 out of 10, Very good, (6)
"Our stay was great, the apartment was close to the bus line and the train. The beds were very comfortable and it was a good size for our family. It was nice to have the off street parking in the back although the rear entrance was a bit disheveled. The building was secure but not entirely sound proof, but that is expected in a basement appartment. I would stay here again on a trip to Chicago. "
The price is HK$850
HK$1,889 total
includes taxes & fees
1 Oct - 2 Oct
Your Perfect 2BR Home w/ Parking
1F Chicago's Little italy Graystone nearDowntown
Exterior

1F Chicago's Little italy Graystone nearDowntown

10.0 out of 10, Exceptional, (152)
"This is an awesome place to stay in Chicago."
1F Chicago's Little italy Graystone nearDowntown
4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!
Fridge, microwave, oven, stovetop

4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!

10.0 out of 10, Exceptional, (5)
4 br/3ba, Great for Large Groups, Garage Parking. Spacious and updated!
Urban Farm Fun with Goats 10 Minutes To Downtown!
Interior

Urban Farm Fun with Goats 10 Minutes To Downtown!

8.0 out of 10, Very good, (2)
"So overall the stay was amazing the goats and chickens were a perfect addition to the stay BUT the neighbors upstairs literally didn’t sleep at al they were banging around moving things at all hours of the night one night it was 2am and they were still going strong so that’s why my rating was low but the host was amazing and sweet. "
Urban Farm Fun with Goats 10 Minutes To Downtown!
3BR Complete and Spacious Apt
TV

3BR Complete and Spacious Apt

9.6 out of 10, Exceptional, (4)
"Spacious and well appointed. Great location with plenty of eating/drinking options within walking distance. "
The price is HK$764
HK$1,944 total
includes taxes & fees
3 Sept - 4 Sept
3BR Complete and Spacious Apt
Bright & Roomy 4BR in Pilsen
Dining

Bright & Roomy 4BR in Pilsen

8.0 out of 10, Very good, (8)
The price is HK$1,154
HK$2,566 total
includes taxes & fees
22 Sept - 23 Sept
Bright & Roomy 4BR in Pilsen
Elizabeth by Coast to Cactus | Chic Artists Loft
Interior

Elizabeth by Coast to Cactus | Chic Artists Loft

9.2 out of 10, Wonderful, (21)
"Great place, excellent location and close to the trains!!!!"
Elizabeth by Coast to Cactus | Chic Artists Loft
Spacious 4BR Near Wicker Park
Fridge, microwave, oven, stovetop

Spacious 4BR Near Wicker Park

10.0 out of 10, Exceptional, (2)
"Had an amazing stay at this Vrbo. Very cozy and comfortable for everyone!"
The price is HK$1,481
HK$3,775 total
includes taxes & fees
1 Oct - 2 Oct
Spacious 4BR Near Wicker Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top West Side Hotel Reviews

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Find out more about West Side

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