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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Featured Cottages in Southwest Side and around

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Recommended hotels in Southwest Side

Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2122)
"Great place to stay!"
The price is €231
includes taxes & fees
22 Sept - 23 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2295)
"Nice place to stay!"
The price is €136
includes taxes & fees
23 Sept - 24 Sept
Freehand Chicago
Best Western Grant Park Hotel
Exterior

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2622)
"Great place to stay for a concert or long weekend."
The price is €131
includes taxes & fees
22 Sept - 23 Sept
Best Western Grant Park Hotel
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Exterior

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

9.6 out of 10, Exceptional, (4)
"It was great it had the basic amenities for a family to enjoy the stay"
The price is €228
includes taxes & fees
29 Sept - 30 Sept
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Exterior

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

8.6 out of 10, Excellent, (20)
"It was great for our needs! Definitely hear EVERYTHING though as usual for most older places in the city."
The price is €186
includes taxes & fees
29 Sept - 30 Sept
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Rainbow Motel
Exterior

Rainbow Motel

2.5 star property
5.0 out of 10, (10)
"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 "
The price is €89
includes taxes & fees
10 Sept - 11 Sept
Rainbow Motel
Carlton Inn Midway
Exterior

Carlton Inn Midway

2.0 star property
6.4 out of 10, (1006)
"Nice place"
The price is €105
includes taxes & fees
11 Sept - 12 Sept
Carlton Inn Midway
Skylark Motel
Front of property

Skylark Motel

2.0 star property
4.6 out of 10, (117)
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
The price is €109
includes taxes & fees
10 Sept - 11 Sept
Skylark Motel
Claridge House
Exterior

Claridge House

4.0 star property
9.0 out of 10, Wonderful, (1357)
"We had a great stay"
The price is €240
includes taxes & fees
11 Sept - 12 Sept
Claridge House
Ohio House Motel
View from property

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Awesome place to stay. "
The price is €120
includes taxes & fees
21 Sept - 22 Sept
Ohio House Motel
Travelodge by Wyndham Downtown Chicago
Exterior

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2335)
"Helpful staff and convenient walking distances to many downtown Chicago attractions "
The price is €133
includes taxes & fees
22 Sept - 23 Sept
Travelodge by Wyndham Downtown Chicago
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (230)
"Great place "
The price is €127
includes taxes & fees
23 Sept - 24 Sept
FOUND Hotel Chicago River North
Hotel Felix River North/Magnificent Mile
City view from property

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2151)
"Great spot, good location, nice rooms. "
Hotel Felix River North/Magnificent Mile
Congress Plaza Hotel
Exterior detail

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9151)
"Very nice place to stay and friendly staff! "
The price is €197
includes taxes & fees
13 Sept - 14 Sept
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very good, (1109)
"Staff was great and loved the breakfast and location!"
The price is €144
includes taxes & fees
22 Sept - 23 Sept
The Chicago Hotel Collection Ambassador Gold Coast
Warwick Allerton - Chicago
City view

Warwick Allerton - Chicago

4.0 star property
8.4 out of 10, Very good, (2916)
"Great location....so close to everything."
The price is €129
includes taxes & fees
23 Sept - 24 Sept
Warwick Allerton - Chicago
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1691)
"Had a great stay! The area is very walkable and convenient!!"
Hotel Saint Clair- Magnificent Mile
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3762)
"Great place to stay "
The price is €173
includes taxes & fees
22 Sept - 23 Sept
citizenM Chicago Downtown
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1022)
"It was a great stay"
The price is €143
includes taxes & fees
2 Oct - 3 Oct
Best Western River North Hotel
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1007)
"Place was very cute, clean and safe "
The price is €169
includes taxes & fees
23 Sept - 24 Sept
Ivy Boutique Hotel
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

Find out more about Southwest Side

Find out more about Southwest Side

Southwest Side Cottages information

Number of reviews
Accommodation
11 Cottages
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