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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Featured Cabin Rentals in Southwest Side

No exact matches found, but these alternatives could be just right

Recommended hotels in Southwest Side

Exterior
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10

Brighton Park
10.0 out of 10, Exceptional, (1)
"Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment [if available]. "
United States
Fabian H.
The price is NZ$404
includes taxes & fees
9 Dec - 10 Dec
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Exterior
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

Brighton Park
9.2 out of 10, Wonderful, (7)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is NZ$579
includes taxes & fees
1 Jan - 2 Jan 2026
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Exterior
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Brighton Park
8.6 out of 10, Excellent, (20)
"Clean and nice. My son loved the arcade game. Would stay again "
United States
Nichole S.
The price is NZ$351
includes taxes & fees
22 Dec - 23 Dec
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Exterior
Carlton Inn Midway

Carlton Inn Midway

2.0 star property
Archer Heights
6.4 out of 10, (1004)
"The room was clean and satisfied our needs. Was handy using their shuttle to Midway Airport."
United States
Charles
The price is NZ$201
includes taxes & fees
1 Jan - 2 Jan 2026
Carlton Inn Midway
Exterior
Skylark Motel

Skylark Motel

2.0 star property
Garfield Ridge
4.6 out of 10, (119)
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
United States
Stephen
The price is NZ$177
includes taxes & fees
9 Dec - 10 Dec
Skylark Motel
Exterior
Rainbow Motel

Rainbow Motel

2.0 star property
Garfield Ridge
5.8 out of 10, (18)
"It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people "
United States
Conner
The price is NZ$214
includes taxes & fees
16 Dec - 17 Dec
Rainbow Motel
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2122)
"Loved and enjoyed our stay"
United States
Luis
The price is NZ$252
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Exterior
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2260)
"Smooth check in and beautiful hotel"
United States
Monique
The price is NZ$253
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2955)
"Great location and great staff!!"
United States
lynne
The price is NZ$169
includes taxes & fees
22 Dec - 23 Dec
Aloft Chicago Mag Mile
Exterior
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3001)
"Very beautiful place to stay"
United States
FaithBrenda
The price is NZ$282
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2943)
"Great rooms, love the bar and amazing breakfast!"
United States
Michelle
The price is NZ$250
includes taxes & fees
9 Dec - 10 Dec
Hotel Riu Plaza Chicago
Front of property
River Hotel

River Hotel

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4850)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is NZ$166
includes taxes & fees
21 Dec - 22 Dec
River Hotel
Exterior
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2116)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
Front of property
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (3006)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is NZ$197
includes taxes & fees
21 Dec - 22 Dec
Warwick Allerton - Chicago
Exterior
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2183)
"Nice Hotel"
United States
Alan
The price is NZ$182
includes taxes & fees
16 Dec - 17 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2747)
"Great food clean room friendly staff"
United States
MARINA
The price is NZ$220
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3449)
"Great place to stay "
United States
RaShawna
The price is NZ$213
includes taxes & fees
14 Dec - 15 Dec
Hilton Chicago/Magnificent Mile Suites
Exterior
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3431)
"Great Hotel!"
United States
Siranush
The price is NZ$265
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1048)
"Great Hotel!"
United States
Wendy
The price is NZ$250
includes taxes & fees
1 Jan - 2 Jan 2026
Hyatt Centric Chicago Magnificent Mile
Exterior
Hyatt Regency Chicago

Hyatt Regency Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3394)
"Everything was amazing, from the staff to the room, amenities simply perfect.!! "
United States
TERESA
The price is NZ$327
includes taxes & fees
22 Dec - 23 Dec
Hyatt Regency Chicago
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

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"Clean, spacious room. Friendly staff. Good, hot breakfast, with different offerings each day. Close by restaurants (and 10% discount with room key) at the adjacent Asian restaurants and French bakery."
Kim 2-night trip
Posted 18 hours ago
Homewood Suites by Hilton Chicago Downtown South Loop

Find out more about Southwest Side

Southwest Side Cabin Rentals information

Number of reviews
40,529
Accommodation
0 Cabin Rentals
Lowest Price
NZ$166
Highest Price
NZ$579

Frequently asked questions

Are there cheap cabins in Southwest Side?
Priced from NZ$166 to NZ$579 a night, escaping the everyday has never been more affordable. Rent one of our cheap cabins in Southwest Side and enjoy the great outdoors without putting a dent in your budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why should I book a cabin in Southwest Side?
For a getaway in nature at an impressive price, there's nothing better than a cabin. Imagine starting your day with the sounds of songbirds and then stepping onto your deck to be surrounded by beautiful views. Choose a cabin in Southwest Side and say "see ya" to the hectic routine of modern life. Whether they're in the mountains, by the beach or someplace else, cabins offer a relaxing, rustic experience you'll always remember.

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