Book Hotels in Southwest Side, IL

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Top Southwest Side hotels

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $191 total per night from Oct 25 to Oct 26
$191 total
Oct 25 - Oct 26
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. ...
"Elevators slow and small and housekeeping is always in them. Housekeeping rude. No lobby store. Rooms small and outdated."

Reviewed on Oct 5, 2026

Opens in a new windowRiver Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 2 to Nov 3
$127 total
Nov 2 - Nov 3
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 ...
"The staff are SPECIAL and EXCEPTIONAL! They made the stay good when I would have rated it poor. Steve and Johnny were AMAZING. The bartender was SUPERB! The room was smaller than I expected. Updates are strongly needed: Add charging stations Elevators are slow Having one Central heating and cooling ..."

Reviewed on Oct 5, 2026

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 Nov 1 to Nov 2
$170 total
Nov 1 - Nov 2
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, ...
"The property was in a prime location for access around the city, the staff was friendly and attentive, two things though the housekeeping service didn’t clean my room not once during my stay I stayed for four days, and the bathroom needs ventilation aka a fan. The overall experience was 3.5/5 if ..."

Reviewed on Oct 5, 2026

Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $179 total per night from Nov 1 to Nov 2
$179 total
Nov 1 - Nov 2
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi ...
Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $171 total per night from Nov 1 to Nov 2
$171 total
Nov 1 - Nov 2
Total with taxes and fees
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, ...
Opens in a new windowEurostars Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $226 total per night from Oct 30 to Oct 31
$226 total
Oct 30 - Oct 31
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, ...
Opens in a new windowHilton Chicago
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$277 nightly
The price is $329 total per night from Oct 31 to Nov 1
$329 total
Oct 31 - Nov 1
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, ...
Opens in a new windowHyatt Regency Chicago
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $169 total per night from Nov 1 to Nov 2
$169 total
Nov 1 - Nov 2
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
Opens in a new windowThe Wade
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $211 total per night from Nov 3 to Nov 4
$211 total
Nov 3 - Nov 4
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also ...
Opens in a new windowFreehand Chicago
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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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Great location, good sized rooms, comfortable beds"
A verified traveler stayed at The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

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