South Side Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Sleep Inn Midway Airport Bedford Park
Bedford Park
Price was $765, price is now $643 per person
$643
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SeatGeek Stadium and Wintrust Sports Complex are located nearby.
The room was disgusting. There were stains on the walls. The toilet had burn marks. I slept with my clothes on and a hoodie over my head. I clearly misread the stars earned.
Reviewed on Jul 27, 2026
Chicago Marriott Midway
Bedford Park
Price was $1,016, price is now $831 per person
$831
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions SeatGeek Stadium and Wintrust Sports Complex are located nearby.
DoubleTree by Hilton Chicago - Alsip
Price was $922, price is now $782 per person
$782
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Alsip. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hollywood Park and Gaelic Park are located nearby.
Fairfield Inn and Suites by Marriott Chicago Midway Airport
Bedford Park
Price was $934, price is now $796 per person
$796
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Wintrust Sports Complex are located nearby.
Hilton Rosemont Chicago O'Hare
Price was $1,174, price is now $1,008 per person
$1,008
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Rosemont Theatre and Fashion Outlets of Chicago are located nearby.
Embassy Suites by Hilton Chicago O'Hare Rosemont
Price was $1,043, price is now $896 per person
$896
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
San Antonio (SAT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, a free airport shuttle, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rosemont Theatre and Fashion Outlets of Chicago are located nearby.
Top Hotel Deals
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
3.04 km from South Side
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn & Suites
8258 Arnt Blvd Watervliet MI
23.98 km from South Side
Book a stay at this family-friendly hotel in Watervliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Starlite Resort
3353 Blue Star Highway Saugatuck MI
30.74 km from South Side
Stay at this motel in Saugatuck. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
117 55th St Grand Junction MI
17.04 km from South Side
Stay at this cabin in Grand Junction. Enjoy free parking, patios, and climate control. Popular attractions Saddle Lake and Upper Scott Lake are located ...
Country Inn & Suites by Radisson, South Haven, MI
1741 Phoenix St South Haven MI
3.38 km from South Side
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
AmericInn by Wyndham Douglas/Saugatuck
2905 Blue Star Hwy Douglas MI
26.84 km from South Side
Book a stay at this business-friendly hotel in Douglas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Suites South Haven near I-96
1755 Phoenix Street South Haven MI
3.44 km from South Side
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in ...
Sun N Sand Resort
176 N. Blue Star Highway South Haven MI
4.79 km from South Side
Stay at this resort in South Haven. Enjoy free parking, daily housekeeping, and a picnic area. Popular attractions Kal Haven Trail and Michigan Maritime Museum ...
The Fields of Michigan
154 68th St South Haven MI
7.17 km from South Side
Book a stay at this spa hotel in South Haven. Enjoy free breakfast, free parking, and an outdoor pool. Popular attractions The Fun Park and Michigan Flywheelers ...
Holiday Inn Express South Haven by IHG
72095 CR 388 South Haven MI
3.16 km from South Side
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DayDreamer Domes
397 Blue Star Hwy South Haven MI
6.57 km from South Side
Book a stay at this spa hotel in South Haven. Enjoy free breakfast, free parking, and room service. Popular attractions Kal Haven Trail and Michigan Maritime ...
Captain's Quarters Motel
3242 Blue Star Highway Saugatuck MI
29.79 km from South Side
Stay at this motel in Saugatuck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Lake Bluff Inn and Suites
76648 11th Avenue South Haven MI
1.81 km from South Side
Book a stay at this family-friendly hotel in South Haven. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Deerlick Creek Beach Park and ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Sep 5 - Tue, Sep 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 3 days ago
$203
Roundtrip
found 3 days ago
Thu, Sep 17 - Mon, Sep 21
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Tue, Sep 15 - Tue, Sep 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 4 days ago
$247
Roundtrip
found 4 days ago
Sat, Sep 5 - Tue, Sep 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Wed, Sep 2 - Sat, Sep 5
LAX
Los Angeles Intl.
MDW
Midway Intl.
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago