Near South Side Vacations from $164

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Your Near South Side Vacation

Lock in a vacation package to Near South Side and immerse yourself in everything this lakeside neighborhood has to offer. Noted for its history, walking and culture, your next exciting adventure can be found right here. Start your trip to Near South Side by checking out nearby attractions such as Millennium Park, Willis Tower and Art Institute of Chicago. Expedia can help turn your ideal Near South Side vacation into reality, no matter your travel plans or budget.

The Latest Near South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $309, price is now $164 per person
$164
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Clean and great service.

Reviewed on Nov 21, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,110, price is now $456 per person
$456
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
17.6/10 Exceptional! (1,075 reviews)
Just slept there overnight.

Reviewed on Nov 23, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $476, price is now $257 per person
$257
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.4/10 Exceptional! (1,264 reviews)
Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe.

Reviewed on Nov 22, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $535, price is now $308 per person
$308
per person
Jan 24 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Great stay. Excellent location.

Reviewed on Nov 23, 2025

Sand Hill On The Lake

Sand Hill On The Lake

2 out of 5
Save 100% on your flight
Price was $658, price is now $380 per person
$380
per person
Dec 31 - Jan 3
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
17.2/10 Exceptional! (83 reviews)
The view on the lake is beautiful and the fireplace made it so cozy during our fall visitl

Reviewed on Nov 10, 2025

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Where to stay in Near South Side

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

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.

Find hotels in Downtown Chicago

Near South Side Hotel Deals

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $145 total per night from Dec 23 to Dec 24
$145 total
Dec 23 - Dec 24
Total with taxes and fees
8.4/10 Very Good! (2,083 reviews)
Room great, lobby bar the best! Christmas tree gorgeous. And free brownie a nice touch!

Reviewed on Nov 22, 2025

Palmer House a Hilton Hotel
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
$87 nightly
The price is $102 total per night from Dec 21 to Dec 22
$102 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (5,275 reviews)
It’s conveniently close to several tourist attractions. Highly recommended! 💯

Reviewed on Nov 20, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $98 total per night from Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,350 reviews)
Room was clean and spacious!

Reviewed on Nov 23, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,686 properties in Near South Side
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 Near South Side

Copernicus Statue showing a statue or sculpture

Lakefront Trail

4.5/5(50 reviews)

Lakefront Trail is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Wander the lakeside and beautiful beaches in the area.

Lakefront Trail
Soldier Field featuring a skyscraper, modern architecture and a city

Burnham Park

4/5(4 reviews)

After visiting Burnham Park, make a plan to see the other sights and activities in Chicago. Stroll along the area's beautiful beaches, or simply savor its top-notch restaurants.

Burnham Park

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$45
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.