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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in Southwest Side

We don't have any properties that match your exact search

Recommended hotels in Southwest Side

Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2073)
"Great place to stay!"
The price is NZ$372
includes taxes & fees
1 Sept - 2 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, (2204)
"Great stay "
The price is NZ$229
includes taxes & fees
3 Sept - 4 Sept
Freehand Chicago
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1301)
"He a great time, clean hotel"
The price is NZ$315
includes taxes & fees
17 Aug - 18 Aug
Claridge House
Rainbow Motel
Interior detail

Rainbow Motel

2.5 star property
5.0 out of 10, (9)
"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 NZ$177
includes taxes & fees
18 Aug - 19 Aug
Rainbow Motel
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (18)
"It was great for our needs! Definitely hear EVERYTHING though as usual for most older places in the city."
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Carlton Inn Midway
Coffee and/or coffee maker

Carlton Inn Midway

2.0 star property
6.4 out of 10, (1004)
"Staff are very friendly:) "
The price is NZ$208
includes taxes & fees
24 Aug - 25 Aug
Carlton Inn Midway
Skylark Motel
Exterior

Skylark Motel

2.0 star property
4.6 out of 10, (114)
"A dump. Next time im forced to choose this place or a floor in the airport, I'll choose the floor."
The price is NZ$212
includes taxes & fees
28 Aug - 29 Aug
Skylark Motel
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (186)
"Great place "
The price is NZ$193
includes taxes & fees
3 Sept - 4 Sept
FOUND Hotel Chicago River North
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Everyone was nice and a great location "
The price is NZ$244
includes taxes & fees
17 Aug - 18 Aug
Ohio House Motel
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2587)
"Location is great"
The price is NZ$217
includes taxes & fees
25 Aug - 26 Aug
Best Western Grant Park Hotel
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8931)
"lovely hotel, room was clean with comfy bed and great facilities. would definitely stay here again "
The price is NZ$373
includes taxes & fees
14 Sept - 15 Sept
Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3692)
"Our stay was wonderful."
The price is NZ$302
includes taxes & fees
26 Aug - 27 Aug
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Exterior

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4.0 star property
9.6 out of 10, Exceptional, (1007)
"Great hotel To stay at :)"
The price is NZ$335
includes taxes & fees
4 Sept - 5 Sept
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3571)
"Great hotel"
The price is NZ$276
includes taxes & fees
2 Sept - 3 Sept
citizenM Chicago Downtown
Swissotel - Chicago
Reception

Swissotel - Chicago

4.5 star property
9.0 out of 10, Wonderful, (2600)
"Great experience with staff, room and overall stay! "
The price is NZ$400
includes taxes & fees
1 Sept - 2 Sept
Swissotel - Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (2039)
"Perfect location, i will stay again"
The price is NZ$246
includes taxes & fees
4 Sept - 5 Sept
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (267)
"Great place. Good stay for family vacation to Chicago"
Level Chicago Fulton Market
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1812)
"Enjoyed our stay"
The price is NZ$243
includes taxes & fees
24 Aug - 25 Aug
Central Loop Hotel
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2289)
"Hotel location, staff and transportation were very good "
The price is NZ$230
includes taxes & fees
3 Sept - 4 Sept
Travelodge by Wyndham Downtown Chicago
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1934)
"Great stay"
The price is NZ$291
includes taxes & fees
24 Aug - 25 Aug
Millennium Knickerbocker 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

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

10/10 Excellent
"It’s good ."
Qingshu 4-night trip
Posted 5 hours ago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical