Book Hotels in Southwest Side, IL

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Nov 13 - Nov 15
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Top Southwest Side hotels

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
71 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $173 total per night from Dec 14 to Dec 15
$173 total
Dec 14 - Dec 15
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, conference space, and valet ...
"Great hotel, amazing experience"

Reviewed on Nov 12, 2026

Opens in a new windowThe Royal Sonesta Chicago Downtown
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $141 total per night from Nov 23 to Nov 24
$141 total
Nov 23 - Nov 24
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 ...
"Great stay"

Reviewed on Nov 13, 2026

Opens in a new windowThe Wade
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 23 to Nov 24
$127 total
Nov 23 - Nov 24
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 ...
"Congress Plaza Hotel was an ideal hotel for its location to many Chicago sites. It is in walking distance to Soldier's Field which allowed us to get to the football game without dealing with traffic issues. Parking was easy to access and the lot was conveniently located behind the hotel."

Reviewed on Nov 13, 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
$116 nightly
The price is $138 total per night from Dec 1 to Dec 2
$138 total
Dec 1 - Dec 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, ...
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
$98 nightly
The price is $117 total per night from Dec 10 to Dec 11
$117 total
Dec 10 - Dec 11
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 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
$116 nightly
The price is $138 total per night from Nov 22 to Nov 23
$138 total
Nov 22 - Nov 23
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
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Nov 27 to Nov 28
$190 total
Nov 27 - Nov 28
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
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $144 total per night from Dec 6 to Dec 7
$144 total
Dec 6 - Dec 7
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
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $154 total per night from Dec 13 to Dec 14
$154 total
Dec 13 - Dec 14
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
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See all available properties in Southwest Side
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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 Wade

The Wade

5 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Great stay"
A verified traveler stayed at The Wade
The Wade

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