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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,110, price is now $615 per person
$615
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,827, price is now $934 per person
$934
per person
Jul 14 - Jul 19
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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 $1,649, price is now $1,011 per person
$1,011
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this 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.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $1,087, price is now $682 per person
$682
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,531, price is now $974 per person
$974
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this 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 $1,295, price is now $842 per person
$842
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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 ...
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 Breedsville North Park are located ...
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 ...
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 ...
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 ...
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 ...
The Inn of Saugatuck
447 Butler St Saugatuck MI
30.05 km from South Side
Stay at this B&B in Saugatuck. Enjoy free breakfast, free WiFi, and cable TV channels. Popular attractions Oval Beach and Butler Street are located nearby.
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 ...
Old Harbor Inn
515 Williams Street South Haven MI
1.32 km from South Side
Stay at this hotel in South Haven. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
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 South Haven Center ...
Waters View Inn
86 North Shore Drive South Haven MI
1.31 km from South Side
Stay at this B&B in South Haven. Enjoy free WiFi, free parking, and a garden. Popular attractions Stanley Johnson Park and Southside Municipal Marina are located ...
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.
Wed, Aug 19 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$150 Roundtrip, found 13 hours ago
$150
Roundtrip
found 13 hours ago
Wed, Aug 19 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 13 hours ago
$154
Roundtrip
found 13 hours ago
Wed, Aug 19 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 3 days ago
$163
Roundtrip
found 3 days ago
Wed, Aug 19 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 13 hours ago
$189
Roundtrip
found 13 hours ago
Tue, Aug 25 - Tue, Sep 8
LAX
Los Angeles Intl.
MDW
Midway Intl.
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago