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! (1,338 reviews)
Oct 21 - Oct 24
3 night stay
Boston (BOS) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,333, price is now $918 per person
$918
per person
found 1 day ago
Comfortable room with a great view and luxuriously soft bed!
Reviewed on Sep 13, 2026
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
$164 nightly
The price is $195 total per night
$195 total
Sep 20 - Sep 21
Total with taxes and fees
Guests of Crowne Plaza Chicago West Loop by IHG enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 57.00 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include conference space, a 24-hour business center, and express check-in.
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Free Cancellation
3.51 mi from city center
$179 nightly
The price is $213 total per night
$213 total
Sep 20 - Sep 21
Total with taxes and fees
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 24-hour business center, and a seasonal outdoor pool.
LIVN - West Loop Chicago
555 West Jackson Boulevard Chicago IL
3.41 mi from city center
$180 nightly
The price is $211 total per night
$211 total
Sep 21 - Sep 22
Total with taxes and fees
Guests of LIVN - West Loop Chicago enjoy features like a 24-hour gym, free WiFi in public areas, and laundry facilities. A multilingual staff is on hand to assist with luggage storage and access to locker space.
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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