Southwest Side Vacation Packages
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Top Southwest Side vacation package deals
Price found within the past 48 hours. Click for updated prices.
Top rated hotels for your Southwest Side vacation package
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
$81 nightly
The price is $95 total per night
$95 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
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
Jan 4 - Jan 5, 2026
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
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
$134 nightly
The price is $153 total per night
$153 total
Dec 30 - Dec 31
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
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.
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- United Center
- Oak Lawn Vacations
- Kam Isaiah Israel Congregation
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- Magnificent Mile Vacations
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- 4944 S Woodlawn Ave
