West Side Vacation Packages

Book a Stay + Flight or Car to save on your trip

Top West Side vacation package deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
4.0-star property

The Emily Hotel

Downtown Chicago
9.2/10 Wonderful! (1,264 reviews)

Mar 22 - Mar 27

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $848, price is now $474 per person
$474
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

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
3.15 mi from city center
$95 nightly
The price is $111 total per night
$111 total
Feb 1 - Feb 2
Total with taxes and fees
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 concierge services, securing valuables, 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

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Free Cancellation
3.51 mi from city center
$118 nightly
The price is $139 total per night
$139 total
Jan 19 - Jan 20
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.
Pool
Free WiFi
The Hoxton Chicago

The Hoxton Chicago

4 out of 5
200 N Green Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
3.1 mi from city center
$169 nightly
The price is $198 total per night
$198 total
Feb 1 - Feb 2
Total with taxes and fees
Guests of The Hoxton Chicago enjoy free WiFi in public areas, a seasonal outdoor pool, and free use of bicycles. Valet parking is available for USD 75 per night. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include free newspapers and a banquet hall.
Pool
Pet friendly
Don't see what you're looking for?
See all available properties in West Side
View all properties
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.
All Inclusive Vacations
All Inclusive Vacations
Family Vacation Packages
Family Vacation Packages
Adventure Vacation Packages
Adventure Vacation Packages

Explore More Ways to Travel with Travelocity