Southwest Side Vacations
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Where to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
Garfield Ridge
3/5(9 area reviews)
Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area.
Find the Best Southwest Side Vacation Packages
Southwest Side Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩241,493 per night from Sep 22 to Sep 23
₩241,493
₩283,489 total
Sep 22 - Sep 23
includes taxes & fees
8.4/10 Very Good! (4,927 reviews)
First time exploring
"To start this hotel is extraordinary, the location is key if you want to explore Chicago. There is a Starbucks conveniently located outside and the grocery store across the street as well as multiple restaurants down the block. I would definitely rebook and consider this hotel as my first pick any ..."
Reviewed on Sep 15, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩203,481 per night from Sep 22 to Sep 23
₩203,481
₩238,867 total
Sep 22 - Sep 23
includes taxes & fees
7.8/10 Good! (9,216 reviews)
"Could use more front desk staff. Quite a line formed behind me"
Reviewed on Sep 18, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is ₩252,312 per night from Sep 22 to Sep 23
₩252,312
₩296,188 total
Sep 22 - Sep 23
includes taxes & fees
8.4/10 Very Good! (3,911 reviews)
"Loved the location. Close proximity to all high end Shopping. The hotel was decent with good amenities."
Reviewed on Sep 18, 2025
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.
Discover the most popular places to visit in Southwest Side
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
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Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
