Southmoor Vacations from $262
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Your Southmoor Vacation
Prepare to experience Southmoor on your own terms with a custom Southmoor vacation package! Uncovering the best parts of this lively city is made easier with a base in a neighborhood such as Flossmoor, which is good for golfing, among other things. You'll want to do a little exploring during your trip to Southmoor. Don't miss leading attractions such as Orland Park Sportsplex, Orland Square and Centennial Park. A couple of quick clicks is all it takes to put together a tailored Southmoor vacation on Expedia.
The Latest Southmoor Vacation Packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $387, price is now $262 per person
$262
per person
Dec 12 - Dec 15
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)
Rooms are very small. You will need to call down for them to bring up a refrigerator. Other than that, everything was okay.
Reviewed on Oct 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $519, price is now $301 per person
$301
per person
Dec 12 - Dec 15
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
We stayed for one night and everything from the staff to the room was absolutely perfect. We definitely would stay here again.
Reviewed on Oct 29, 2026
Where to stay in Southmoor
Find the best Southmoor areas and neighborhoods for the activities you enjoy most. Learn more about Southmoor
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Southmoor Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $129 total per night from Nov 10 to Nov 11
$129 total
Nov 10 - Nov 11
Total with taxes and fees
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $158 total per night from Nov 27 to Nov 28
$158 total
Nov 27 - Nov 28
Total with taxes and fees
8.6/10 Excellent! (3,494 reviews)
"Staff are on strike due to not being paid living wages and being forced to work mandatory overtime. Rooms are not being serviced and there are noisy protests. But Hilton is still happy to collect the “resort” fee from you! Find a hotel that doesn’t put corporate greed above the well-being of their ..."
Reviewed on Oct 29, 2026
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $141 total per night from Nov 22 to Nov 23
$141 total
Nov 22 - Nov 23
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Rooms are very small. You will need to call down for them to bring up a refrigerator. Other than that, everything was okay."
Reviewed on Oct 29, 2026
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.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.