Near South Side Vacations from $375
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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.
Level Chicago Fulton Market
Downtown Chicago
Price was $857, price is now $557 per person
$557
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
Weird space w the way the bed is no access off the side and the counter was stained badly. There was a 28$ additional amenity fee that they slapped on upon check in. The pool is closed and didn’t use the weight room it was a one night stay. over priced but could be ok for a long stay w the kitchen
Reviewed on Nov 6, 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
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.
Near South Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,111 reviews)
"Great room, I hope the second elevator is fixed soon."
Reviewed on Nov 7, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 9 to Nov 10
$138 total
Nov 9 - Nov 10
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundable
$115 nightly
The price is $137 total per night from Dec 6 to Dec 7
$137 total
Dec 6 - Dec 7
Total with taxes and fees
8.8/10 Excellent! (5,590 reviews)
"Un hotel con vista espectacular. Personal súper calificado. Ubicado en la mejor zona y muy accesible para poder llegar caminando a donde quieras."
Reviewed on Nov 7, 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.
Stay near popular Near South Side attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.