Southmoor Vacations from $421
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $3,177, price is now $1,774 per person
$1,774
per person
Sep 13 - Sep 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Could not ask for a better location--walking distance to so many attractions. Hotel was beautiful, and the staff was very nice. Buffet breakfast was excellent, and there is a lovely rooftop bar, but no restaurant or room service (but you can order certain foods and pick them up--we did not partake, so can't comment). We enjoyed our stay immensely, and would not hesitate to stay there again.
Reviewed on Aug 3, 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
$144 nightly
The price is $171 total per night from Aug 30 to Aug 31
$171 total
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
$211 nightly
The price is $251 total per night from Sep 1 to Sep 2
$251 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,233 reviews)
"Great Stay. I will be staying there every time I visit Chicago."
Reviewed on Aug 3, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
$194 nightly
The price is $231 total per night from Aug 30 to Aug 31
$231 total
Aug 30 - Aug 31
Total with taxes and fees
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
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.