South Side Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by RVOutlawz
South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Wood Dale
Save 100% on your flight
Price was $381, price is now $253 per person
$253
per person
Nov 19 - Nov 23
found 1 hour ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Woodfield Mall are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $713, price is now $441 per person
$441
per person
Nov 25 - Nov 29
found 13 hours 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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $718, price is now $460 per person
$460
per person
Nov 25 - Nov 29
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $598, price is now $415 per person
$415
per person
Nov 25 - Nov 29
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $632, price is now $444 per person
$444
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $737, price is now $521 per person
$521
per person
Nov 25 - Nov 29
found 13 hours 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.
Mon, Nov 3 - Sat, Nov 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Tue, Nov 4 - Fri, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 6 days ago
$110
Roundtrip
found 6 days ago
Tue, Nov 4 - Fri, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Fri, Nov 7 - Mon, Nov 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 3 days ago
$179
Roundtrip
found 3 days ago
Fri, Nov 7 - Mon, Nov 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago