
Southwest Side Holidays
- Plan, book, travel with confidence
Better together
Save up to S$134 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Where to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side

Back of the Yards
2 out of top 10 points of interest in this area
While there might not be top attractions in Back of the Yards, you can explore the larger area and discover places like Bridgeport Art Center and Zhou B Art Center.
Top hotels in Southwest Side

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$267 per night from 4 Aug to 5 Aug
S$267
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,972 reviews)
"The area was pretty nice, and hotel was remodeled in some areas. Didnt like the bathroom was dirty the bucket wasnt empty when we arrived"
Reviewed on 15 Jul, 2025

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is S$395 per night from 24 Jul to 25 Jul
S$395
24 Jul - 25 Jul
includes taxes & fees
9/10 Wonderful! (2,049 reviews)
"8lmicr"
Reviewed on 16 Jul, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$217 per night from 17 Aug to 18 Aug
S$217
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,449 reviews)
"I stayed at this 9"
Reviewed on 16 Jul, 2025
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.
Popular places to visit

Wrigley Field
4.5/5(40 reviews)
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

McCormick Place
4.5/5(36 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Millennium Park
4.5/5(147 reviews)
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
What to do in Southwest Side

Wendella's 90-min Chicago River Architecture Tour
S$52
per adult
94% of travellers recommend

Chicago By Night River & Lake Cruise
S$58
per adult
94% of travellers recommend
Frequently asked questions
More trip options
Expedia's Latest Trends
Hotels
- K Hotel 1515
- Mercure Kuala Lumpur Shaw Parade
- McCormick Place hotels
- 5 Star Hotels in Bukit Bintang
- 5 Star Hotels in Kamala
- Best Western Plus Grosvenor Airport Hotel
- Gloria Outlets hotels
- Jeeva Klui Resort
- Chau Long Sapa 2 Hotel
- V Hotel
- Sunshine City Prince Hotel
- Holiday Inn Resort Alpensia Pyeongchang by IHG
- Private Holiday Homes St. John's Island
- Veriu Central
- Hôtel 34B - Astotel
- Twinstar Hotel
- Wonder Mountain Valley Resort
- Crowne Plaza Kunming City Centre by IHG
- Valero Grand Suites by Swiss-Belhotel Makati
- Lunar Cappadocia Hotel
Activities