Southmoor Vacations from $666
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,012, price is now $666 per person
$666
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!
Reviewed on Jun 18, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,611, price is now $927 per person
$927
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,135, price is now $694 per person
$694
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.
Reviewed on Jun 19, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,078, price is now $676 per person
$676
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
We had a great stay. The breakfast was amazing. Our room was super clean and comfortable. The staff super helpful and cheerful.
Reviewed on Jun 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,275, price is now $836 per person
$836
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Staff was excellent. Everyone was always friendly and took time to make sure you were having a good experience.
Reviewed on Jun 19, 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
5 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
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,140 reviews)
"Complicated"
Reviewed on Jun 19, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $143 total per night from Jul 5 to Jul 6
$143 total
Jul 5 - Jul 6
Total with taxes and fees
7.6/10 Good! (2,617 reviews)
"For travelers looking for a cheaper option near the Loop, it's difficult to beat. A half block off Michigan Avenue and the adjacent Grant Park, the hotel is older and no-frills (it even has window air-conditioners) but it is clean, quiet and comfortable, and the front desk is helpful. If all you're ..."
Reviewed on Jun 19, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
$228 nightly
The price is $271 total per night from Jul 8 to Jul 9
$271 total
Jul 8 - Jul 9
Total with taxes and fees
9.2/10 Wonderful! (1,129 reviews)
"Loved the hotel overall, the breakfast was really good and the rooms were super clean and comfortable. For a place that charges a resort fee, we were underwhelmed. The only perk was a $15 a day bar credit. There was no pool or hot tub or anything that made it feel like a resort fee was warranted. ..."
Reviewed on Jun 19, 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.
Discover the most popular places to visit in Southmoor
Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(4,925 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$154
per adult
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.