South Side Vacations from $602
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
The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $925, price is now $602 per person
$602
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.
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
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,002, price is now $626 per person
$626
per person
Sep 24 - Sep 27
found 2 days 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
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
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 would absolutely stay here again and highly recommend the Omni to anyone visiting Chicago.
Reviewed on Jul 14, 2026
Where to stay in South Side
Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
Hyde Park
3 out of top 10 points of interest in this area
Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan.
Stay near popular South Side attractions
What to do in South Side
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
South Side Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $143 total per night from Jul 20 to Jul 21
$143 total
Jul 20 - Jul 21
Total with taxes and fees
8.2/10 Very Good! (1,041 reviews)
"The room was clean and nice and the breakfast was good but expensive. The main thing that really bothered me was that the Wi-Fi didn’t work at all. It kept dropping the connection and it was really hard to figure out the next day of our trip when I couldn’t use the Internet.The employees were nice ..."
Reviewed on Jul 14, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$154 nightly
The price is $183 total per night from Aug 10 to Aug 11
$183 total
Aug 10 - Aug 11
Total with taxes and fees
9/10 Wonderful! (1,257 reviews)
"Overall, stay was great. We had a bad smell in the room when we arrived and upon entry each time. I suspect it may have been humidity related. Otherwise, all was great. Thanks for having us."
Reviewed on Jul 14, 2026
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $116 total per night from Jul 21 to Jul 22
$116 total
Jul 21 - Jul 22
Total with taxes and fees
7.4/10 Good! (399 reviews)
"I Didn't like the room I had at my Stay on July 12th through July 23 at 11am at motel 6. They need some repairs on some of they rooms.But they do have some rooms that are Okay ."
Reviewed on Jul 13, 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.
Find the Best South Side Vacation Packages
South Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
More vacations you might like
Explore a world of travel with Expedia
- Cna Center
- House of Blues Chicago
- Chicago Place Mall
- Elijah Muhammad House
- Hyde Park Vacations
- Robie House
- Muddy Waters’ House
- Ohio Street Beach
- Ping Tom Memorial Park
- Harold Washington Library Center
- Lakefront Trail
- University of Chicago
- Crown Fountain
- Bridgeport Art Center
- Unity Temple
- Navy Pier
- Chicago Children's Museum
- Goodman Theater
- Maggie Daley Park
- Buckingham Fountain
- Richard J. Daley Center
- South Commons Vacations
- Daley Plaza
- Grace Abbott Homes Vacations
- United Center
- Griffin Museum of Science and Industry
- Depaul University-Loop Campus
- Pontiac Building
- Shops at North Bridge
- Willis Tower
- Jane Addams' Hull-House Museum
- 333 West Wacker Drive
- Robert W Roloson Houses
- Chinatown Vacations
- Driehaus Museum
- Chase Tower
- Civic Opera House
- Lincoln Park Conservatory
- Millennium Park
- Oak Street Beach
- Burnham Park
- 900 North Michigan Shops
- Maxwell Street Market
- Chicago Architecture Foundation
- Tribune Tower
- Wrigley Building
- Chicago Cultural Center
- Symphony Center
- 311 S Wacker Dr
- Magnificent Mile Vacations
- Chicago City Hall
- Art Institute of Chicago
- Skydeck Ledge
- Michigan Avenue
- The Loop Vacations
- Ida B Wells House
- Chicago Riverwalk
- Water Tower Place
- Chicago Loop Synagogue
- Picasso Statue
- South Loop Vacations
- Marina City
- Chicago Vacations
- Chicago Board of Trade Building
- Chicago Museum Campus Vacations
- Michigan Avenue Bridge
- Downtown Chicago Vacations
- Chicago Symphony Orchestra
- University of Illinois Chicago
- Rookery
- Grant Park
- Sr Crown Hall
- Wrigley Field
- Cadillac Palace Theatre
- Roosevelt University
- American Police Center & Museum
- Canalport Riverwalk Park
- Obama's House
- Santa Fe Building
- Montrose Beach
- Merchandise Mart
- Marshall Field Building
- Old Colony Building
- The Salt Shed
- Carbide and Carbon Building
- Lincoln Park Zoo
- Monadnock Building
- Mccormick Tribune Center
- Marquette Building
- North Avenue Beach
- Cibc Theatre
- Zhou B Art Center
- Holy Name Cathedral
- Film Row Cinema
- Fisher Building
- Columbia College Chicago
- Illinois Institute of Technology
- Auditorium Building and Theatre
- Gen. John Logan Memorial
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
