West Side Vacation Packages
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Top West Side vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,182 reviews)
Nov 6 - Nov 9
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $919, price is now $665 per person
$665
per person
found 1 day ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.
Reviewed on Jul 26, 2025
Top rated hotels for your West Side vacation package
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Free Cancellation
3.15 mi from city center
The price is $210 total per night
$210 total
per night
Sep 1 - Sep 2
Guests of Crowne Plaza Chicago West Loop by IHG enjoy a gym, free WiFi in public areas, and conference space. Self parking is offered for USD 54.00 per day. Multilingual staff at the 24-hour front desk can assist with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a 24-hour business center, express check-in, and express check-out.
Pet friendly
Free WiFi
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street, Chicago, IL
Free Cancellation
3.51 mi from city center
The price is $189 total per night
$189 total
per night
Sep 2 - Sep 3
At Holiday Inn & Suites Chicago - Downtown by IHG, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 65 per day. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, a seasonal outdoor pool, and a microwave in a common area.
Pool
Free WiFi
Hyatt Place Chicago Medical/University District
1835 W Harrison Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.84 mi from city center
The price is $160 total per night
$160 total
per night
Sep 1 - Sep 2
Guests of Hyatt Place Chicago Medical/University District enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 30 per day. The 24-hour front desk has staff always at the ready. Additional amenities include a 24-hour business center, laundry facilities, and a banquet hall.
Breakfast included
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.
