Book 5 Star Hotels in Southwest Side

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Oct 21 - Oct 22
Tonight
Check prices in Southwest Side for tonight, Oct 21 - Oct 22
Oct 22 - Oct 23
Tomorrow night
Check prices in Southwest Side for tomorrow night, Oct 22 - Oct 23

Featured Southwest Side 5 Stars Hotels

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.28 mi from city center
$176 nightly
The price is $207 total per night
$207 total
Nov 20 - Nov 21
Total with taxes and fees
Guests of The Allegro Royal Sonesta Hotel Chicago Loop enjoy a 24-hour gym, WiFi in public areas, and conference space. Valet parking is offered for USD 77 per night. The 24-hour front desk has multilingual staff ready to assist with concierge services and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a fireplace in the lobby, a reception hall, and an ATM.
Pet friendly
Air conditioning
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
6.99 mi from city center
$129 nightly
The price is $152 total per night
$152 total
Nov 9 - Nov 10
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.65 mi from city center
$131 nightly
The price is $154 total per night
$154 total
Nov 9 - Nov 10
Total with taxes and fees
At citizenM Chicago Downtown, guests have access to a gym, free WiFi in public areas, and a 24-hour business center. The 24-hour front desk has staff standing by to help with securing valuables and luggage storage. Additional amenities include coffee/tea in a common area, a computer station, and express check-in.
Free WiFi
Restaurant
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.86 mi from city center
$122 nightly
The price is $144 total per night
$144 total
Nov 9 - Nov 10
Total with taxes and fees
Guests staying at Hilton Garden Inn Chicago Downtown/Magnificent Mile enjoy an indoor pool, a gym, and free WiFi in public areas. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. Additional amenities include meeting rooms, express check-out, and a banquet hall.
Pool
Pet friendly
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
7.92 mi from city center
$144 nightly
The price is $169 total per night
$169 total
Nov 9 - Nov 10
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
7.92 mi from city center
$95 nightly
The price is $112 total per night
$112 total
Nov 10 - Nov 11
Total with taxes and fees
Guests of Freehand Chicago enjoy features like a 24-hour gym, free WiFi in public areas, and express check-in. Self parking is offered for USD 49 per night. Multilingual staff at the 24-hour front desk can assist with tours or tickets, dry cleaning/laundry, and luggage storage. Additional amenities include express check-out, laundry facilities, and a fireplace in the lobby.
Pet friendly
Free WiFi
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
8.14 mi from city center
$117 nightly
The price is $137 total per night
$137 total
Nov 12 - Nov 13
Total with taxes and fees
At Warwick Allerton - Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 72 per day. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, securing valuables, and dry cleaning/laundry. Other amenities at this family-friendly hotel include a conference center, a 24-hour business center, and a computer station.
Free WiFi
Air conditioning
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
8.35 mi from city center
$97 nightly
The price is $114 total per night
$114 total
Nov 18 - Nov 19
Total with taxes and fees
The Whitehall Hotel, BW Premier Collection features a gym, free WiFi in public areas, and a business center. Self parking is offered for USD 56 per night. The 24-hour front desk has staff standing by to help with securing valuables, concierge services, and luggage storage. Other amenities at this boutique hotel include a meeting room, a computer station, and free newspapers.
Breakfast included
Pet friendly
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
8.49 mi from city center
$117 nightly
The price is $137 total per night
$137 total
Nov 16 - Nov 17
Total with taxes and fees
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a business center, express check-out, and a porter/bellhop.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Southwest Side
View all properties
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.

Best 5 star hotels in Southwest Side

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Southwest Side. After all, treating yourself to the finer things is what vacations are about. 

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Southwest Side hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Southwest Side 5 star hotels and resorts typically offer luxury amenities such as:

  • Gourmet restaurant
  • Full-service fitness center with pool
  • Luxury spa 
  • Welcome gifts upon arrival
  • Top-of-the-line beds and linens 
  • Designer personal care products
  • Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Southwest Side with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place: 

  • Search hotels by price, ranging from $112 to $207
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 4,926 5 star hotels in Southwest Side!

Southwest Side hotels essential information

Accommodation
4,926 hotels
Lowest Price
$112
Highest Price
$207
Popular hotels
Congress Plaza Hotel, Freehand Chicago, Hilton Chicago/Magnificent Mile Suites, citizenM Chicago Downtown, Embassy Suites by Hilton Chicago Downtown River North, The Allegro Royal Sonesta Hotel Chicago Loop, Hilton Garden Inn Chicago Downtown/Magnificent Mile, Warwick Allerton - Chicago, The Whitehall Hotel, BW Premier Collection

Recent Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

5/5 Excellent
"Parking was terrible and expensive. Recommend valet parking. Staff, very hard to talk to and i arrived at 3:30 scheduled to check in at 4 pm. Room wasn't available until 4;30. Staff wasn't to concerned."
A verified traveler stayed at Embassy Suites by Hilton Chicago Downtown River North
Posted 22 hours ago
Embassy Suites by Hilton Chicago Downtown River North

More to Explore