South Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in South Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,417, price is now CA $1,050 per person
CA $1,050
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Incredible!!
Reviewed on Oct 31, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $3,076, price is now CA $2,269 per person
CA $2,269
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
My only suggestions. The batteries in the rechargeable TV remotes die too quickly and the room service ordering software on the tablet was lacking pictures. Options for an omelet were red and unavailable to select. So unless they were out of eggs, that was an issue. And the bedside tablet nightlight is nice, but too bright. These were a struggle to come up with because the service was impeccable.
Reviewed on Oct 30, 2026
Where to stay in South Side
Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like North Beach and Michigan Maritime Museum.
South Side Hotel Deals
Overlook South Haven Harbor steps from South Beach and Downtown
South Haven MI
10/10 Exceptional! (207 reviews)
"We just returned from a girls' (sisters/daughters) weekend in South Haven-what a wonderful time! The house was lovely-a short walk to town or to the beach. The view of the Black River was a bonus. Our hosts met is when we arrived and friendly ad reassuring that if there was anything we needed, to ..."
Reviewed on Oct 25, 2026
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from Nov 10 to Nov 11
CA $89
CA $99 total
Nov 10 - Nov 11
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Was good but the elevator don’t work very well !"
Reviewed on Oct 29, 2026
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
117 55th St Grand Junction MI
The price is CA $165 per night from Nov 30 to Dec 1
CA $165
CA $293 total
Nov 30 - Dec 1
includes taxes & fees
9.4/10 Exceptional! (109 reviews)
"Rates and fees were very confusing. Night to night the rental price fluctuated wildly. Then there were additional fees that added a significant amoubt to a four night stay. When they say tiny cabin they mean it. So just be aware that if you are into "glamping" it might not be for you. Musty/mildew ..."
Reviewed on Oct 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.