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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
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2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Top Holiday Rentals in Southwest Side

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (951)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is Rp3.505.559
Rp4.601.367 total
includes taxes & fees
19 Oct - 20 Oct
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (554)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (363)
"Great place to stay. Loved it!"
Level Chicago – Old Town
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
8.0 out of 10, Very good, (378)
"Great stay!"
The price is Rp2.100.237
Rp2.465.468 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (236)
"Great location and lovely amenities. "
The price is Rp2.241.192
Rp2.630.936 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (360)
"nice area, shops nearby"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (679)
"great room, clean good space and close to places "
The price is Rp2.523.103
Rp2.961.870 total
includes taxes & fees
22 Oct - 23 Oct
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (207)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (53)
"Place was in a great location close to good restaurants "
The price is Rp2.523.103
Rp2.961.870 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
Kasa River North Chicago
The Gem Museum Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is Rp3.402.832
Rp3.895.513 total
includes taxes & fees
28 Oct - 29 Oct
The Gem Museum Suites
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
Wrigleyville Suites
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (181)
"Great location!!!"
The price is Rp2.382.148
Rp2.796.404 total
includes taxes & fees
2 Nov - 3 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (62)
"Good "
The price is Rp1.203.716
Rp1.359.958 total
includes taxes & fees
8 Oct - 9 Oct
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.6 out of 10, Good, (141)
"Very clean and affordable "
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Stylish Apartment near Chicago Downtown
Classic Apartment | Private kitchen

Stylish Apartment near Chicago Downtown

2.0 star property
The price is Rp3.296.037
Rp5.716.334 total
includes taxes & fees
16 Oct - 17 Oct
Stylish Apartment near Chicago Downtown
Art Villa
Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is Rp4.384.116
Rp10.664.508 total
includes taxes & fees
13 Oct - 14 Oct
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is Rp3.227.881
Rp3.789.208 total
includes taxes & fees
4 Nov - 5 Nov
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Studio | Iron/ironing board, free WiFi

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.2 out of 10, Wonderful, (19)
"The stay lacked in shelf space as well as other amenities that could be useful. "
Ground Floor Studios in Chicago by 747 Lofts
At Home in Oak Park
Apartment, Private Bathroom | Terrace/patio

At Home in Oak Park

3.5 star property
9.8 out of 10, Exceptional, (6)
"Great location in Oak Park- walkable, wondering area for restaurants and strolling through the beautiful neighborhoods."
The price is Rp2.446.822
Rp4.409.586 total
includes taxes & fees
2 Nov - 3 Nov
At Home in Oak 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 Southwest Side Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Right across the street from the navy pier! Everything about the hotel is amazing as far as the lobby, weight room, pool, and room. The only thing that wasn’t good was the beds themselves. The weren’t comfortable. Other than that great place to stay."
Anthony 3-night trip
Posted 12 hours ago
The Wade

Find out more about Southwest Side

Find out more about Southwest Side

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