Near South Side Vacations from $156
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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.
Illinois Beach Hotel
Save 100% on your flight
Price was $261, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (384 reviews)
I like the place, it is very quiet and safe, but the room requires better cleaning, the balcony was not clean and blinds need to be washed, anyhow i liked it.
Reviewed on Aug 21, 2025
The Emily Hotel
Downtown Chicago
Price was $1,322, price is now $641 per person
$641
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug 22, 2025
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $621 per person
$621
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location
Reviewed on Aug 22, 2025
The Stella Hotel & Ballroom
Downtown Kenosha
Save 100% on your flight
Price was $316, price is now $191 per person
$191
per person
Oct 30 - Nov 2
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (CHI)
9.4/10 Exceptional! (1,005 reviews)
Nice hotel, wish it had it's own parking lot.
Reviewed on Aug 23, 2025
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
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,211 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."
Reviewed on Aug 20, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Aug 25 to Aug 26
$168 total
Aug 25 - Aug 26
Total with taxes and fees
7.8/10 Good! (8,996 reviews)
Great view! Safe location for food music and park
"Got a very good rate during an event that had filled up many nearby hotels. Lovely sparkling-clean room, rather small, a firm king bed, dresser, & table. It felt cozy, not crowded, enough drawers and closet space, nice-size bathroom with shower-tub. Room has nice ornate details. 10th-floor sunrise ..."
Reviewed on Aug 24, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Sep 3 to Sep 4
$179 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,765 reviews)
"Everyone was very helpful and polite. The room was clean and spacious. My kids loved the breakfast and snacks at night."
Reviewed on Aug 23, 2025
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.
Discover the most popular places to visit in Near South Side
Lakefront Trail
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.
Burnham Park
After visiting Burnham Park, make a plan to see the other sights and activities in Chicago. Stroll along the area's lakeside, or simply savor its top-notch restaurants.
Things to do
Chicago's Ultimate City Bike Tour
$60
per adult
100% of travellers recommend
Big Bus Chicago Essential Ticket + 360 Chicago
$84
per adult
Big Bus Chicago Essential & Shoreline Architecture Cruise
$99
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.