Book Hotels in Southwest Side, IL

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Top Southwest Side hotels

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, ...
"The room was spacious and the bed was very comfortable. The check in was easy and they gave us a voucher for a drink in the lounge bar. We had a very nice stay. Great location, the river walk is with in walking distance."

Reviewed on Oct 4, 2026

Opens in a new windowHyatt Regency Chicago
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, ...
"There's no noise isolation in the building unfortunately"

Reviewed on Oct 4, 2026

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, ...
"I stayed here for the Chicago Half Marathon and had a great experience! The location was honestly perfect, especially if you’re visiting for a race or just want to explore Chicago. There are plenty of restaurants nearby, and it’s a great place for runners since you can easily run along the river ..."

Reviewed on Oct 4, 2026

Opens in a new windowHilton Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $140 total per night from Nov 2 to Nov 3
$140 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the business center, express ...
"Breakfast was good and staff were very friendly!"

Reviewed on Oct 4, 2026

Opens in a new windowSonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 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 ...
"May have been the place to stay 80 years ago Just awful really… Peeling wallpaper Doors painted when they were closed. Then opened Air conditioning sucked. Analog Tv"

Reviewed on Oct 4, 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, ...
"they over booked the hotel for my night that I was staying, so they did not have a room for me when I got to the hotel"

Reviewed on Oct 4, 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 ...
"Great location"

Reviewed on Oct 4, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $199 total per night from Nov 1 to Nov 2
$199 total
Nov 1 - Nov 2
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
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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"It was a beautiful property in an ideal location."
A verified traveler stayed at InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG

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