Search Deals onSouth Side Vacation Packages
South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont
Save 100% on your flight
Price was $732, price is now $482 per person
$482
per person
Aug 26 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Fashion Outlets of Chicago are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,425, price is now $871 per person
$871
per person
Aug 27 - Aug 31
found 1 day 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.
DoubleTree by Hilton Chicago - Alsip
Save 100% on your flight
Price was $846, price is now $545 per person
$545
per person
Aug 26 - Sep 1
found 1 day ago
Roundtrip flight included
Houston (IAH) 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 Gaelic Park and Lake Katherine Nature Center are located nearby.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,231, price is now $793 per person
$793
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,326, price is now $869 per person
$869
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,571, price is now $1,035 per person
$1,035
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,587, price is now $1,060 per person
$1,060
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 4 restaurants, and a rooftop terrace. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Villa Christina
Greater Grand Crossing
Save 100% on your flight
Price was $1,324, price is now $917 per person
$917
per person
Aug 26 - Sep 1
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Griffin Museum of Science and Industry and Rate Field are located nearby.
3-4 Night Vacations in South Side
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in South Side
Baymont by Wyndham South Haven
1555 Phoenix Rd South Haven MI
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
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 Inn & Suites
8258 Arnt Blvd Watervliet MI
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Starlite Resort
3353 Blue Star Highway Saugatuck MI
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
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
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
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 ...
DayDreamer Domes
397 Blue Star Hwy South Haven MI
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 ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Aug 17 - Wed, Sep 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Thu, Aug 27 - Sat, Aug 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$258 Roundtrip, found 1 hour ago
$258
Roundtrip
found 1 hour ago
Mon, Oct 12 - Sat, Oct 17
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$338 Roundtrip, found 9 hours ago
$338
Roundtrip
found 9 hours ago
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$453 Roundtrip, just found
$453
Roundtrip
just found