South Side Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Saratoga Motel By Capital O Near Midway Airport Chicago IL
Price was $458, price is now $334 per person
$334
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Popular attraction SeatGeek Stadium is located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $976, price is now $475 per person
$475
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,772, price is now $1,114 per person
$1,114
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $654, price is now $452 per person
$452
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,838, price is now $1,287 per person
$1,287
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $763, price is now $543 per person
$543
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Top Hotel Deals
Old Harbor Inn
515 Williams Street, South Haven, MI
1.32 km from South Side
Stay at this 3-star hotel in South Haven. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean ...
Baymont by Wyndham South Haven
1555 Phoenix Rd, I-196 Exit 20, South Haven, MI
3.05 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 ...
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 ...
Starlite Resort
3353 Blue Star Highway, Saugatuck, MI
30.73 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. ...
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 ...
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 ...
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 ...
Historic Hotel Nichols
201 Center St, South Haven, MI
1.33 km from South Side
Stay at this hotel in South Haven. Enjoy free WiFi, a conference center, and concierge services. Popular attractions Warner Vineyards and Michigan Maritime Museum ...
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
1.92 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 ...
Comfort Inn & Suites
8258 Arnt Blvd, Watervliet, MI
23.98 km from South Side
Stay at this hotel in Watervliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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. Our guests praise the helpful staff in our reviews. Popular attractions ...
Great Lakes Inn and Suites
9814 M-140, South Haven, MI
1.8 km from South Side
Stay at this motel in South Haven. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff and the overall value in our reviews. ...
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.
Thu, Nov 13 - Sat, Nov 15
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 2 hours ago
$73
Roundtrip
found 2 hours ago
Fri, Nov 14 - Thu, Nov 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$142 Roundtrip, found 2 hours ago
$142
Roundtrip
found 2 hours ago
Tue, Dec 2 - Tue, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 3 days ago
$172
Roundtrip
found 3 days ago
Tue, Dec 2 - Tue, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Wed, Dec 31 - Sat, Jan 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 2 hours ago
$257
Roundtrip
found 2 hours ago