Book 2 Star Hotels in Southwest Side
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
Featured Southwest Side 2 Stars Hotels

Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
6.82 mi from city center
$139 nightly
The price is $163 total per night
$163 total
Dec 30 - Dec 31
Total with taxes and fees
Guests staying at Hilton Chicago enjoy an indoor pool, a gym, and a sauna. Valet parking is offered for USD 88.00 per day. The 24-hour front desk has multilingual staff ready to assist with luggage storage, dry cleaning/laundry, and securing valuables. Other amenities at this historic hotel include free WiFi in public areas, a hot tub, and a conference center.
Pool
Hot Tub

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.23 mi from city center
$156 nightly
The price is $179 total per night
$179 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and access to locker space. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Pool
Spa

Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.31 mi from city center
$127 nightly
The price is $149 total per night
$149 total
Dec 30 - Dec 31
Total with taxes and fees
Guests of Silversmith Hotel Chicago Downtown enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 79 per night. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. Additional amenities include conference space, a 24-hour business center, and a computer station.
Free WiFi
Air conditioning

Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.68 mi from city center
$89 nightly
The price is $104 total per night
$104 total
Dec 25 - Dec 26
Total with taxes and fees
At Club Quarters Hotel Wacker at Michigan, Chicago, guests have access to a gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 76 per day. The 24-hour front desk has staff standing by to help with luggage storage, dry cleaning/laundry, and concierge services. 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 business center, coffee/tea in a common area, and a computer station.
Pet friendly
Free WiFi

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
7.92 mi from city center
$94 nightly
The price is $111 total per night
$111 total
Jan 4 - Jan 5, 2026
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 luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included

Eurostars Magnificent Mile
660 North State Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
8 mi from city center
$94 nightly
The price is $110 total per night
$110 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
Guests staying at Eurostars Magnificent Mile enjoy access to a full-service spa, a gym, and a sauna. Valet parking is offered for USD 68 per night. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and tours or tickets. Other amenities at this spa hotel include free WiFi in public areas, meeting rooms, and conference space.
Spa
Free WiFi

Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
8.14 mi from city center
$91 nightly
The price is $107 total per night
$107 total
Jan 14 - Jan 15, 2026
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 concierge services, 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
105 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
8.35 mi from city center
$83 nightly
The price is $97 total per night
$97 total
Jan 5 - Jan 6, 2026
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 58 per night. The 24-hour front desk has staff standing by to help with concierge services, securing valuables, 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
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
8.49 mi from city center
$89 nightly
The price is $105 total per night
$105 total
Jan 5 - Jan 6, 2026
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, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, express check-out, and a porter/bellhop.
Pet friendly
Free WiFi
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.
Southwest Side hotels essential information
Accommodation | 5,125 hotels |
|---|---|
Lowest Price | $97 |
Highest Price | $179 |
Popular hotels | Hilton Chicago/Magnificent Mile Suites, Palmer House a Hilton Hotel, Silversmith Hotel Chicago Downtown, Club Quarters Hotel Wacker at Michigan, Chicago, Hilton Chicago, Eurostars Magnificent Mile, Warwick Allerton - Chicago, The Whitehall Hotel, BW Premier Collection, Embassy Suites by Hilton Chicago Downtown River North |
Recent Reviews

Hilton Chicago/Magnificent Mile Suites
5/5 Excellent
"Staff was incredibly welcoming upon arrival and was fantastic throughout the stay! Perfect location for walking as well as catching the train, can’t recommend enough"
A verified traveler stayed at Hilton Chicago/Magnificent Mile Suites
Posted 22 hours ago
More to Explore
- Hotels near Midway Intl.
- Englewood Hotels
- 4 Star Hotels in Canaryville
- 4 Star Hotels in Cicero
- 5 Star Hotels in Cicero
- 5 Star Hotels in North Lawndale
- 5 Star Hotels in Corwith
- 5 Star Hotels in Douglas Park
- 5 Star Hotels in Burbank
- 4 Star Hotels in Brighton Park
- Boutique Hotels in Brighton Park
- Brighton Park Hotels
- 5 Star Hotels in South Englewood
- Hotels near United Center
- 5 Star Hotels in Grand Boulevard
- 5 Star Hotels in Oakland
- 4 Star Hotels in West Elsdon
- 5 Star Hotels in West Elsdon
- West Elsdon Hotels
- 5 Star Hotels in Hometown
- 4 Star Hotels in Woodlawn
- Pet Friendly Hotels in Glendale
- 5 Star Hotels in Bridgeport
- 4 Star Hotels in Kenwood
- New City Hotels
- Motels in Pulaski Station
- 4 Star Hotels in Gage Park
- Gage Park Hotels
- Hotels near Marquette Park
- 5 Star Hotels in Ducktown
- 5 Star Hotels in Hyde Park
- 3 Star Hotels in Evergreen Park
- 4 Star Hotels in South Loop
- 5 Star Hotels in South Loop
- 5 Star Hotels in Pilsen
- Apartments in 35th-Archer Station
- Condo Rentals in 35th-Archer Station
- Resorts in 35th-Archer Station
- 4 Star Hotels in Essex
- 5 Star Hotels in Ashburn
- Cottages in Halsted Station
- Inns in Halsted Station
- Motels in Halsted Station
- 4 Star Hotels in Chatham Fields
- 3 Star Hotels in Archer Heights
- Cheap Hotels in Chicago
- Hotels with Hot Tubs in Chicago
- Romantic Getaways & Hotels in Chicago
- Chicago Hotels
- Apartments in Ashland-63rd Station
- Hotels near Ashland-63rd Station
- Inns in Ashland-63rd Station
- 2 Star Hotels in Grace Abbott Homes
- 3 Star Hotels in Grace Abbott Homes
- Hotels with Free Parking in Downtown Chicago
- Downtown Chicago Hotels
- Flights from Midway Intl.
- Flights from Tampa (TPA) to Chicago (MDW)
- Flights to Chicago
- Flights from Atlanta to Chicago
- Flights from Austin to Chicago
- Flights from Boston to Chicago
- Flights from Charlotte to Chicago
- Flights from Chicago
- Flights from Cincinnati to Chicago
- Flights from Cleveland to Chicago
- Flights from Columbus to Chicago
- Flights from Dallas to Chicago
- Flights from Denver to Chicago
- Flights from Detroit to Chicago
- Flights from Houston to Chicago
- Flights from Kansas City to Chicago
- Flights from Las Vegas to Chicago
- Flights from Los Angeles to Chicago
- Flights from Memphis to Chicago
- Flights from Miami to Chicago
- Flights from Minneapolis - St. Paul to Chicago
- Flights from Nashville to Chicago
- Flights from New Orleans to Chicago
- Flights from New York to Chicago
- Flights from Orlando to Chicago
- Flights from Philadelphia to Chicago
- Flights from Phoenix to Chicago
- Flights from Portland to Chicago
- Flights from Raleigh to Chicago
- Flights from Salt Lake City to Chicago
- Flights from San Antonio to Chicago
- Flights from San Francisco to Chicago
- Flights from Seattle to Chicago
- Flights from St. Louis to Chicago
- Flights from Toronto to Chicago
- Flights from Washington to Chicago
- Flights from Omaha to Chicago
- Flights from Pittsburgh to Chicago
- Flights from Fort Lauderdale to Chicago
- Flights from Newark to Chicago
- Flights from Tampa to Chicago
- Flights from Jacksonville to Chicago


