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Our top choices for Southwest Side hotels

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.4 out of 10, Very good, (1,000 reviews)
"Friendly staff and clean room"
United States
Alisa
The price is NZ$235
includes taxes & fees
13 Jan - 14 Jan
Holiday Inn Chicago – Midway Airport S by IHG

Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
6.4 out of 10, (1,001 reviews)
"It is a good place to stay."
United States
Paul Adrian
The price is NZ$201
includes taxes & fees
18 Jan - 19 Jan
Carlton Inn Midway

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.6 out of 10, (119 reviews)
"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
13 Jan - 14 Jan
Skylark Motel

Rainbow Motel

Rainbow Motel
2.0 star property
Garfield Ridge
5.8 out of 10, (18 reviews)
"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$216
includes taxes & fees
1 Feb - 2 Feb
Rainbow Motel

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,231 reviews)
"Fantastic stay! Looking forward to staying here again!!"
United States
Amber
The price is NZ$175
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Chicago - Magnificent Mile

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,972 reviews)
"The room was nice, the area was perfect for walking distance for food and activities. "
United States
Alexis
The price is NZ$203
includes taxes & fees
10 Feb - 11 Feb
The Godfrey Hotel Chicago

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,725 reviews)
"Great place to stay"
United States
Kohei
The price is NZ$367
includes taxes & fees
21 Jan - 22 Jan
InterContinental Chicago Magnificent Mile by IHG

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,432 reviews)
"The Hotel was amazing great location "
United States
Donnisha
The price is NZ$365
includes taxes & fees
24 Jan - 25 Jan
Hyatt Regency Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,032 reviews)
"All around a nice stay for the holiday "
United States
Alec
The price is NZ$156
includes taxes & fees
18 Jan - 19 Jan
Aloft Chicago Mag Mile

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,055 reviews)
"Great stay"
United States
Kramer
The price is NZ$167
includes taxes & fees
25 Jan - 26 Jan
Club Quarters Hotel Wacker at Michigan, Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,933 reviews)
"Clean and comfy room, friendly staff, great location. "
United States
Agata
The price is NZ$275
includes taxes & fees
4 Feb - 5 Feb
Arlo Chicago

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North
3.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,188 reviews)
"Great stay!"
United States
Tea
The price is NZ$218
includes taxes & fees
25 Jan - 26 Jan
Aloft Chicago Downtown River North

AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,004 reviews)
"Very nice cozy hotel "
United States
CARLA
The price is NZ$206
includes taxes & fees
12 Feb - 13 Feb
AC Hotels by Marriott Chicago Downtown

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,695 reviews)
"Great stay!!!"
United States
Lorenzo Martrel
The price is NZ$183
includes taxes & fees
18 Jan - 19 Jan
Hilton Chicago/Magnificent Mile Suites

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,067 reviews)
"Amazing location, excellent service and great pool and hot tub. "
United States
Tim
The price is NZ$252
includes taxes & fees
18 Jan - 19 Jan
Hyatt Centric Chicago Magnificent Mile

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,182 reviews)
"Stay was great and in a great location!! "
United States
Ashley
The price is NZ$211
includes taxes & fees
29 Jan - 30 Jan
citizenM Chicago Downtown

Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,489 reviews)
"Beautiful hotel. Great location!"
United States
Pamila
The price is NZ$182
includes taxes & fees
25 Jan - 26 Jan
Cambria Hotel Chicago Loop - Theatre District

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,363 reviews)
"Perfect with a pub next door!"
United States
Chad
The price is NZ$167
includes taxes & fees
24 Jan - 25 Jan
Club Quarters Hotel, Central Loop, Chicago

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,589 reviews)
"Great location and breakfast.. can be a bit pricey but worth it. "
Canada
Shaurya
The price is NZ$256
includes taxes & fees
18 Jan - 19 Jan
voco Chicago Downtown - Riverwalk by IHG

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4,903 reviews)
"Would stay there again"
United States
Zach
The price is NZ$167
includes taxes & fees
25 Jan - 26 Jan
River Hotel
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