Near South Side Vacations from AED1,163

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The Latest Near South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
Aug 26 - Aug 28
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,269 reviews)
Safe and convenient location The staff was friendly and helpful!

Reviewed on 4 June 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Aug 26 - Aug 28
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,598 reviews)
The property was in a great location and is beautiful. It was clean and well maintained. We had a few issues with a breakfast buffet. I highly recommend ordering from the menu instead. Also, with amenities in the room. The staff were quick to fix the issues and to make things right.

Reviewed on 4 June 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
Aug 26 - Aug 28
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
10/10 Exceptional! (1 review)
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
Aug 26 - Aug 28
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
nice hotel clean nice restaurants the room needed a coat of paint on the baseboards

Reviewed on 5 June 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 26 - Aug 28
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Beautiful hotel and wonderful staff!

Reviewed on 21 May 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 showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Near South Side Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 526 per night from Jul 3 to Jul 4
AED 526
AED 617 total
3 Jul - 4 Jul
includes taxes & fees
7.8/10 Good! (8,826 reviews)
"The facility has a great location in walking distance to many attractions. The family suite had a small bathroom with limited space."

Reviewed on 3 June 2025

Congress Plaza Hotel
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AED 450 per night from Jul 1 to Jul 2
AED 450
AED 528 total
1 Jul - 2 Jul
includes taxes & fees
9.2/10 Wonderful! (3,134 reviews)
"Nice clean hotel. Close to it all downtown"

Reviewed on 2 June 2025

citizenM Chicago Downtown
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
The price is AED 559 per night from Jun 29 to Jun 30
AED 559
AED 656 total
29 Jun - 30 Jun
includes taxes & fees
8.8/10 Excellent! (2,274 reviews)
"We stayed one night however all of the employees we had an interaction with were all very pleasant. The room was nice and comfortable. Desk staff were all very kind and helpful. The staff working outside by the door were very kind and helpful with questions we had about directions and ..."

Reviewed on 30 May 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,446 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.

Discover the most popular places to visit in Near South Side

McCormick Place showing a high rise building and a city

McCormick Place

4.5/5(1,805 reviews)

During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.

McCormick Place
Soldier Field featuring a skyscraper, modern architecture and a city

Soldier Field

4.5/5(1,256 reviews)

Soldier Field is one of the more well-known attractions to visit during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Soldier Field
Field Museum of Natural History showing a city

Field Museum of Natural History

4.5/5(1,399 reviews)

You can spend time studying the exhibits at Field Museum of Natural History during your trip to Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.

Field Museum of Natural History