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.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $459, price is now $309 per person
$309
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Ritz-Carlton, Chicago
Downtown Chicago
Price was $1,641, price is now $1,044 per person
$1,044
per person
Dec 22 - Dec 28
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,448, price is now $519 per person
$519
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,337, price is now $1,291 per person
$1,291
per person
Dec 13 - Dec 20
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 $902, price is now $534 per person
$534
per person
Dec 23 - Dec 28
found 19 hours 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $614, price is now $378 per person
$378
per person
Dec 18 - Dec 22
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.
DoubleTree by Hilton Chicago - Alsip
Price was $586, price is now $394 per person
$394
per person
Dec 22 - Dec 27
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (MDW)
Stay at this 4-star 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 Hollywood Park and Gaelic Park are located nearby.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was $510, price is now $347 per person
$347
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
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, I-196 Exit 20, 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 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 ...
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
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 ...
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 ...
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 ...
Yelton Manor Bed & Breakfast
140 North Shore Drive, South Haven, MI
Stay at this 3-star B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Warner Vineyards ...
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, Nov 27 - Tue, Dec 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 3 days ago
$102
Roundtrip
found 3 days ago
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$280 Roundtrip, found 3 days ago
$280
Roundtrip
found 3 days ago
Tue, Jan 6 - Mon, Jan 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$364 Roundtrip, found 3 days ago
$364
Roundtrip
found 3 days ago
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$389 Roundtrip, found 3 days ago
$389
Roundtrip
found 3 days ago
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- Saugatuck Center For the Arts Vacations
- Kal Haven Trail Vacations
- 12 Corners Vineyards Vacations