Search Southwest Side hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Southwest Side

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2826)
"Excellent hotel in a great location."
The price is NZ$464
includes taxes & fees
1 Sept - 2 Sept
L7 Chicago by LOTTE

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1185)
"Friendly staff, rooms very clean, food was excellent "
The price is NZ$1,032
includes taxes & fees
29 Aug - 30 Aug
The Emily Hotel

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1309)
"He a great time, clean hotel"
The price is NZ$369
includes taxes & fees
19 Aug - 20 Aug
Claridge House

Carlton Inn Midway

2.0 star property
6.4 out of 10, (1007)
"Staff are very friendly:) "
The price is NZ$208
includes taxes & fees
19 Aug - 20 Aug
Carlton Inn Midway

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
19 Aug - 20 Aug
Rainbow Motel

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$207
includes taxes & fees
31 Aug - 1 Sept
Skylark Motel

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very good, (1087)
"Beautiful hotel, we were able to walk everywhere we needed to get to! tons of shopping and food close by. "
The price is NZ$303
includes taxes & fees
19 Aug - 20 Aug
The Chicago Hotel Collection Ambassador Gold Coast

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2047)
"Very good place "
The price is NZ$369
includes taxes & fees
21 Aug - 22 Aug
Hyatt Centric The Loop Chicago

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2613)
"Great experience with staff, room and overall stay! "
The price is NZ$364
includes taxes & fees
1 Sept - 2 Sept
Swissotel - Chicago

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1056)
"Wonderful Stay."
The price is NZ$535
includes taxes & fees
31 Aug - 1 Sept
Pendry Chicago

Thompson Chicago, by Hyatt

4.5 star property
9.2 out of 10, Wonderful, (1199)
"Perfect location, great staff and comfortable bed"
The price is NZ$381
includes taxes & fees
2 Sept - 3 Sept
Thompson Chicago, by Hyatt

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1021)
"Best place we have stayed in Chicago in a long time. "
The price is NZ$365
includes taxes & fees
24 Aug - 25 Aug
Hyatt Centric Chicago Magnificent Mile

Chicago Athletic Association, a Hyatt Hotel

4.5 star property
9.0 out of 10, Wonderful, (1005)
"Fantastic place to stay….close to the lake, shopping and dining."
The price is NZ$505
includes taxes & fees
21 Aug - 22 Aug
Chicago Athletic Association, a Hyatt Hotel

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very good, (1010)
"Great stay"
The price is NZ$285
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Chicago - Magnificent Mile by IHG

Viceroy Chicago

4.5 star property
9.4 out of 10, Exceptional, (1071)
"We had a great stay!"
The price is NZ$563
includes taxes & fees
1 Sept - 2 Sept
Viceroy Chicago

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1996)
"Pool area and deck were great for the family, beds were comfortable, location is great."
The price is NZ$300
includes taxes & fees
24 Aug - 25 Aug
DoubleTree by Hilton Chicago - Magnificent Mile

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2215)
"Great stay "
The price is NZ$226
includes taxes & fees
26 Aug - 27 Aug
Freehand Chicago

Sofitel Chicago Magnificent Mile

4.5 star property
9.4 out of 10, Exceptional, (2106)
"Staff were helpful and location was great "
The price is NZ$458
includes taxes & fees
1 Sept - 2 Sept
Sofitel Chicago Magnificent Mile

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2081)
"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

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1945)
"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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and S.S. Peter and Paul Church as you discover things to see and do in Southwest Side.

Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews