West Side Vacations from $574

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The Latest West Side vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Lodge Geneva National
Four Seasons Hotel Chicago
Hampton Inn & Suites Chicago Medical District UIC
Sable at Navy Pier Chicago, Curio Collection by Hilton
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West Side Hotel Deals

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
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $202 total per night from Jul 5 to Jul 6
$202 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (2,320 reviews)
"King size bed was the entire room and hangers in closet were hanging half way out."

Reviewed on Jul 2, 2026

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $199 total per night from Jul 6 to Jul 7
$199 total
Jul 6 - Jul 7
Total with taxes and fees
8.6/10 Excellent! (1,046 reviews)
"Love the pool located roof top"

Reviewed on Jul 2, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
$320 nightly
The price is $380 total per night from Jul 26 to Jul 27
$380 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,321 reviews)
"Very close to shopping, eating, and interstate. Great location. We walked to most of what we wanted to do."

Reviewed on Jul 2, 2026

The Emily Hotel
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.

Find the Best West Side Vacation Packages

West Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.