South Addison Vacations from $345
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The Latest South Addison Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $773, price is now $403 per person
$403
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $674, price is now $389 per person
$389
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue.
However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).
Reviewed on Oct 22, 2025
Where to stay in South Addison
Find the best South Addison areas and neighborhoods for the activities you enjoy most. Learn more about South Addison
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.
South Addison Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Nov 24 to Nov 25
$136 total
Nov 24 - Nov 25
Total with taxes and fees
7.8/10 Good! (9,567 reviews)
LOVED the room and the view was spectacular! The location could not have been any more convenient. Lobby was beautiful. Our room had a separate living room with bay windows looking out over Lake Michigan and the city. The bedroom was fantastic with a comfortable bed and pillows. We slept so well. ...
Reviewed on Oct 24, 2025
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
$120 nightly
The price is $141 total per night from Nov 24 to Nov 25
$141 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (1,958 reviews)
The room was very nice and clean. The bed was really comfortable. Staff was very helpful and the restaurant was excellent. Definitely would stay here again.
Reviewed on Oct 20, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Nov 16 to Nov 17
$129 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,145 reviews)
Hotel was everything i needed for a work trip
Reviewed on Oct 25, 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 South Addison
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.