South Deering Vacations from $250

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Your South Deering Vacation

Golfing, nature, adventure, fun — you'll find it all in South Deering. Discover the best of this neighborhood with a customized South Deering vacation package. When it's time to get out and explore, you'll find lots of awesome attractions nearby including Abbott Park, Harborside International Golf Center and Calumet Park. Tick off one or all during your trip to South Deering. Expedia is here to help put your plans into action. Book your ultimate South Deering vacation now.

The Latest South Deering Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
Save 100% on your flight
Price was $383, price is now $250 per person
$250
per person
Nov 13 - Nov 16
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.4/10 Very Good! (1,014 reviews)
Reservation and check out was easy

Reviewed on Oct 2, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,418, price is now $831 per person
$831
per person
Nov 25 - Dec 2
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
The building and the apartment was excellent

Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $606, price is now $357 per person
$357
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Everything was amazing. From the room itself, the breakfast and the staff

Reviewed on Oct 2, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $833, price is now $542 per person
$542
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Clean room. Great staff

Reviewed on Oct 2, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $508, price is now $344 per person
$344
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
We stayed at The Sable last weekend and we have a serious complaint: our own home now feels deeply, deeply inadequate. The views of the city were so stunning, they ruined my ability to enjoy the view of my neighbor's fence. And the service was so fantastic, I'm now struggling to readjust to the real world. To make matters worse, the bars and restaurants downstairs were way too convenient and fun—it’s a real problem when the best spot in the city is right in your lobby. It's a dangerous place that sets unrealistic expectations for daily life. 10/10, would have my reality ruined again.

Reviewed on Oct 2, 2025

Where to stay in South Deering

Find the best South Deering areas and neighborhoods for the activities you enjoy most. Learn more about South Deering
Downtown Chicago showing a city

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.

Find hotels in Downtown Chicago

South Deering Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,258 reviews)
"Love this place"

Reviewed on Oct 2, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $159 total per night from Oct 22 to Oct 23
$159 total
Oct 22 - Oct 23
Total with taxes and fees
7.8/10 Good! (2,422 reviews)
"I stayed in a shared quad with females, The room wasn’t bad for the price they do however need to install more lighting in the rooms because there was only one light working in the room plus the one in the bathroom so the room was very dark. The staff are great!!! They were super helpful answered ..."

Reviewed on Oct 2, 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $221 total per night from Nov 3 to Nov 4
$221 total
Nov 3 - Nov 4
Total with taxes and fees
8.4/10 Very Good! (5,023 reviews)
"Clean , a great location and the amenities are awesome"

Reviewed on Oct 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,236 properties in South Deering
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in South Deering

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.