Search Deals onSouth Side Vacation Packages
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South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
citizenM Chicago Downtown
Downtown Chicago
Save 100% on your flight
Price was $424, price is now $276 per person
$276
per person
Jan 14 - Jan 18
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
DoubleTree by Hilton Chicago Schaumburg
Save 100% on your flight
Price was $467, price is now $298 per person
$298
per person
Jan 18 - Jan 23
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free parking, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and FireZone are located nearby.
Hyatt Place Chicago/ Schaumburg
Save 100% on your flight
Price was $513, price is now $327 per person
$327
per person
Jan 18 - Jan 23
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Woodfield Mall and Jump Zone are located nearby.
DoubleTree by Hilton Chicago - North Shore Conference Center
Save 100% on your flight
Price was $509, price is now $346 per person
$346
per person
Jan 18 - Jan 23
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Skokie. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions North Shore Center for the Performing Arts and Adagio Teas are located nearby.
DoubleTree by Hilton Chicago - Oak Brook
Save 100% on your flight
Price was $442, price is now $303 per person
$303
per person
Jan 18 - Jan 23
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Oak Brook. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Oakbrook Center Mall and Drury Lane Theater are located nearby.
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $463, price is now $317 per person
$317
per person
Jan 14 - Jan 18
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Save 100% on your flight
Price was $506, price is now $350 per person
$350
per person
Jan 18 - Jan 23
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre 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 ...
Old Harbor Inn
515 Williams Street South Haven MI
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 ...
Captain's Quarters Motel
3242 Blue Star Highway Saugatuck MI
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 Breedsville North Park are located ...
Lake Bluff Inn and Suites
76648 11th Avenue South Haven MI
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 ...
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. ...
Holiday Inn Express South Haven by IHG
72095 CR 388 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 breakfast and the helpful ...
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 ...
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.
Thu, Feb 12 - Mon, Feb 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Fri, Jan 9 - Mon, Jan 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$401 Roundtrip, found 3 days ago
$401
Roundtrip
found 3 days ago
Wed, Dec 24 - Thu, Jan 1
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$463 Roundtrip, found 16 hours ago
$463
Roundtrip
found 16 hours ago