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Top Southwest Side hotels

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
A gym, self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. A convenience store and luggage storage are also ...
"Loved the check-in and check-out process. Very easy and excellent communication through texts, emails and the Kasa desk in the lobby. The security via the fobs and designated elevators was excellent. The water pressure was good in the shower, and the towels were fluffy. The view in this corner unit ..."

Reviewed on Aug 18, 2026

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Opens in a new windowKasa Magnificent Mile Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$267 nightly
The price is $318 total per night from Sep 8 to Sep 9
$318 total
Sep 8 - Sep 9
Total with taxes and fees
This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, ...
"Great spot"

Reviewed on Aug 18, 2026

Opens in a new windowHyatt Regency Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $181 total per night from Aug 23 to Aug 24
$181 total
Aug 23 - Aug 24
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...
"We had a quick stay but it was lovely."

Reviewed on Aug 18, 2026

Opens in a new windowHyatt Regency O'Hare Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $230 total per night from Sep 7 to Sep 8
$230 total
Sep 7 - Sep 8
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
"Waited a long time to check in. Loved the games in the lobby! Pool was great! Housekeeping didn’t clean our room on the second night- we came back to a dirty room with no sheets in a bed and the do not disturb sign was on the door. I called the front desk, but no one came so then I had to go track ..."

Reviewed on Aug 18, 2026

Opens in a new windowHilton Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $130 total per night from Sep 8 to Sep 9
$130 total
Sep 8 - Sep 9
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center ...
Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $170 total per night from Aug 30 to Aug 31
$170 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, ...
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $163 total per night from Aug 23 to Aug 24
$163 total
Aug 23 - Aug 24
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. ...
Opens in a new windowRiver Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
$222 nightly
The price is $264 total per night from Aug 30 to Aug 31
$264 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. ...
Opens in a new windowThe Allegro Royal Sonesta Hotel Chicago Loop
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Fully refundableReserve now, pay when you stay
$289 nightly
The price is $344 total per night from Sep 2 to Sep 3
$344 total
Sep 2 - Sep 3
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities and in-room ...
Opens in a new windowFairmont Chicago at Millennium Park
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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.

Recent Southwest Side hotel reviews by fellow wanderers

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"We had a quick stay but it was lovely."
A verified traveler stayed at Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago

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