Find hotels in Southwest Side, IL from $64

  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Southwest Side hotels

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
$98 nightly
The price is $115
Mar 15 - Mar 16
Total with taxes and fees
Carlton Inn Midway

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)
"Clean room, friendly staff, good conditioning "
United States
Khanh
$121 nightly
The price is $140
Apr 5 - Apr 6
Total with taxes and fees
Holiday Inn Chicago – Midway Airport S by IHG

Skylark Motel

Skylark Motel
2.0 star property
Garfield Ridge
4.8 out of 10, (121 reviews)
"Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal."
United States
Stephen
$82 nightly
The price is $97
Mar 19 - Mar 20
Total with taxes and fees
Skylark Motel

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,001 reviews)
"Great location and not far from places!!"
United States
Savanna
$97 nightly
The price is $114
Apr 5 - Apr 6
Total with taxes and fees
Le Méridien Essex Chicago

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, (2,390 reviews)
"Great location, friendly staff. "
United States
Brian
$174 nightly
The price is $205
Mar 24 - Mar 25
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (491 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
$84 nightly
The price is $99
Apr 6 - Apr 7
Total with taxes and fees
FOUND Hotel Chicago River North

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,127 reviews)
"Clean rooms friendly staff, great location "
United States
Roxana
$108 nightly
The price is $127
Mar 22 - Mar 23
Total with taxes and fees
Aloft Chicago Mag Mile

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,212 reviews)
"Helpful staff, great location with views, restaurant and bar on-site"
United States
Natalie
$152 nightly
The price is $178
Mar 29 - Mar 30
Total with taxes and fees
Swissotel - Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2,802 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
$80 nightly
The price is $94
Mar 25 - Mar 26
Total with taxes and fees
Freehand Chicago

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (9,917 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
$101 nightly
The price is $118
Apr 1 - Apr 2
Total with taxes and fees
Congress Plaza Hotel

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (2,687 reviews)
"Perfect location "
United States
Kelly
$95 nightly
The price is $112
Mar 24 - Mar 25
Total with taxes and fees
Best Western Grant Park Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,033 reviews)
"Great location and nice hotel! "
United States
James
$99 nightly
The price is $116
Mar 25 - Mar 26
Total with taxes and fees
River Hotel

La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,698 reviews)
"Everything was fantastic, room, staff, breakfast "
United States
Nathan
$109 nightly
The price is $127
Mar 22 - Mar 23
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Chicago Downtown

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,901 reviews)
"Great hotel great location. "
United States
Michael
$104 nightly
The price is $122
Mar 22 - Mar 23
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites

Hilton Garden Inn Chicago Downtown Riverwalk

Hilton Garden Inn Chicago Downtown Riverwalk
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,876 reviews)
"Pleasant stay "
United States
Kathya
$114 nightly
The price is $134
Mar 30 - Mar 31
Total with taxes and fees
Hilton Garden Inn Chicago Downtown Riverwalk

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1,713 reviews)
"Location and staff"
United States
Mary Catherine
$129 nightly
The price is $151
Mar 31 - Apr 1
Total with taxes and fees
The Wade

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,344 reviews)
"Loved this hotel!"
United States
Ellen
$106 nightly
The price is $124
Mar 22 - Mar 23
Total with taxes and fees
DoubleTree by Hilton Chicago - Magnificent Mile

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,388 reviews)
"Staff very friendly and we had a great time."
United States
Juan
$127 nightly
The price is $149
Mar 19 - Mar 20
Total with taxes and fees
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,980 reviews)
"Excellent location for shops,restaurants and casino."
United States
Deborah
$91 nightly
The price is $107
Mar 15 - Mar 16
Total with taxes and fees
ACME Hotel Chicago, Outset Collection by Hilton

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,031 reviews)
"Great stay"
United States
Jessica
$114 nightly
The price is $134
Mar 18 - Mar 19
Total with taxes and fees
Warwick Allerton - 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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Great Lakes attractions

Learn more about Southwest Side

Explore attractions like Balzekas Museum of Lithuanian Culture and Ephraim Bajar Cultural Center as you discover things to see and do in Southwest Side.

Chicago, IL which includes landscape views and an airport
Photo by by Midway Intl Airport
Open Photo by by Midway Intl Airport

Top Southwest Side Hotel Reviews

More cheap stays in Southwest Side

Hotels in Southwest Side with star-rating

Explore a world of travel with Expedia