Southwest Side Vacations from $558

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The Latest Southwest Side vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Hotel Riu Plaza Chicago
Omni Chicago Hotel
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Whitehall Hotel, BW Premier Collection
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Where to stay in Southwest Side

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What to do in Southwest Side

Southwest Side Hotel Deals

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $308 total per night from Jul 26 to Jul 27
$308 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,878 reviews)
"very good experience overall, few concerns: - didnt like the bar ambience/availability - inconvenient lobby system - especially for folks checking in later in the night"

Reviewed on Jul 8, 2026

Omni Chicago Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $183 total per night from Jul 9 to Jul 10
$183 total
Jul 9 - Jul 10
Total with taxes and fees
8.2/10 Very Good! (1,713 reviews)
"Nice place to stay"

Reviewed on Jul 8, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$201 nightly
The price is $239 total per night from Jul 9 to Jul 10
$239 total
Jul 9 - Jul 10
Total with taxes and fees
8/10 Very Good! (10,204 reviews)
"Great location. The building has so much history and yes it is old but they’ve done a nice job in trying to keep it up."

Reviewed on Jul 8, 2026

Congress Plaza 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 Southwest Side Vacation Packages

Southwest 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.