Near South Side Vacations from $611
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 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.
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $939, price is now $611 per person
$611
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
We came up to the hotel because my daughter was having surgery at a nearby hospital. Javier & Richard we're amazing at the valet in front of the hotel. Javier took care of all of our needs even brought the luggage up to our room upon check in. Stephen took Amazing care of our family during our stay. We had to extend from one night to two, and even being sold out, they still found a way to accommodate our needs. Keith went through an itemized bill upon checkout. I cannot wait to visit this property in the future. A bonus, it's right over the harry potter store and has endless choices for shopping and food.
Reviewed on Jul 14, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,163, price is now $704 per person
$704
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The location was perfect close to a lot of activities the included breakfast buffet was really great.
Reviewed on Jul 14, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,513, price is now $927 per person
$927
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
We stayed for our first time in Chicago. Loved the area. The hotel is clean and well maintained. The staff is amazing. Thank you, Marena for welcoming us.
Reviewed on Jul 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,141, price is now $734 per person
$734
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Very clean nice workers and amazing views
Reviewed on Jul 14, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $964, price is now $622 per person
$622
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super.
Reviewed on Jul 12, 2026
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
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.
Near South Side Hotel Deals
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
$237 nightly
The price is $281 total per night from Aug 9 to Aug 10
$281 total
Aug 9 - Aug 10
Total with taxes and fees
9.2/10 Wonderful! (1,205 reviews)
"Property was laid out nicely and in a great location. Checking in was very quick and the people at the front desk were very courteous and helpful. Room was cleaned up daily and I had a great stay."
Reviewed on Jul 13, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from Aug 3 to Aug 4
$193 total
Aug 3 - Aug 4
Total with taxes and fees
8.8/10 Excellent! (2,846 reviews)
"This is the third time we’ve stayed, and every time we’ve enjoyed, property is well kept, nice rooms, great staff, wonderful breakfast, would definitely recommend!"
Reviewed on Jul 14, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $193 total per night from Jul 27 to Jul 28
$193 total
Jul 27 - Jul 28
Total with taxes and fees
8.2/10 Very Good! (1,753 reviews)
"Nice property and location. Was charged 3 times for parking."
Reviewed on Jul 14, 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
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
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.