South Chicago Vacation Packages
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Top Holiday Package Deals in South Chicago
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Aug. 11 - Aug. 15
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8/10 Very Good! (2,380 reviews)
We stayed here for a weekend and had a mixed experience. It was nice that they had a breakfast, and the options were good. However, the area was extremely crowded, and the eggs were not great (powdered and runny) and there just was not adequate seating. We were put on the 11th floor which is the top floor, which meant always waiting a really long time for an elevator. It also meant our room was extremely HOT and the sofa bed area did not get any AC at all so our son was pretty uncomfortable. The area in Chicago is mixed, some good restaurants but also very loud, very crowded and not somewhere you would want to walk at night alone. Would not stay here again.
Reviewed on Jun. 17, 2024
W Chicago - Lakeshore
Downtown Chicago
Save 100% on your flight
per person
Aug. 24 - Aug. 31
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very Good! (1,006 reviews)
Good stay at the W, staff was very nice and organized.
Would stay there again for sure.
Reviewed on Jun. 17, 2024
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 22 - Aug. 25
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,230 reviews)
Location is amazing, super friendly staff. Will definitely be back soon
Reviewed on Jun. 17, 2024
Where to stay in South Chicago
Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
Downtown Chicago
4 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 Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
South Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Jul. 1 to Jul. 2
CA $187
CA $219 total
includes taxes & fees
Jul 1 - Jul 2
7.6/10 Good! (7,017 reviews)
"Lovely stay right in the middle of it all."
Reviewed on Jun. 17, 2024
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $250 per night from Jul. 1 to Jul. 2
CA $250
CA $293 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,388 reviews)
"Hector the bellman was very kind and accommodating."
Reviewed on Jun. 15, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Jul. 2 to Jul. 3
CA $199
CA $234 total
includes taxes & fees
Jul 2 - Jul 3
8.6/10 Excellent! (2,952 reviews)
"This was such a conveniently located hotel. We were able to walk to so many places. The guy that checked us in was super friendly and set the tone for a really nice stay. I also really appreciated to cold filtered water stations all over to refill our water bottles. I would definitely stay here ..."
Reviewed on Jun. 16, 2024
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.
Explore other types of vacation packages
Frequently asked questions
Discover the most popular places to visit in South Chicago
Wrigley Field
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Six Flags Great America
4.5/5(5 reviews)
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
Navy Pier
4.5/5(459 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
CA $255
Per adult
76% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
CA $64
Per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.