Search Deals onSouth Side Vacation Packages
South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
Price was $495, price is now $348 per person
$348
per person
May 14 - May 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 AMC Streets Of Woodfield 20 are located nearby.
The Wade
Downtown Chicago
Price was $1,448, price is now $1,039 per person
$1,039
per person
Jun 3 - Jun 8
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,194, price is now $857 per person
$857
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,553, price is now $955 per person
$955
per person
Jun 4 - Jun 8
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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $2,357, price is now $1,471 per person
$1,471
per person
May 14 - May 19
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 parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,646, price is now $1,078 per person
$1,078
per person
Jun 1 - Jun 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,686, price is now $1,126 per person
$1,126
per person
May 14 - May 19
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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,371, price is now $926 per person
$926
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
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
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. ...
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 ...
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 ...
Save an average of 15% on thousands of hotels when you're signed in
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 ...
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 ...
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 ...
The Inn of Saugatuck
447 Butler St Saugatuck MI
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.
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.
Sat, Apr 25 - Sat, May 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 6 days ago
$101
Roundtrip
found 6 days ago
Wed, May 20 - Wed, May 27
LAX
Los Angeles Intl.
MDW
Midway Intl.
$241 Roundtrip, found 7 hours ago
$241
Roundtrip
found 7 hours ago
Mon, May 25 - Tue, May 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$316 Roundtrip, found 12 hours ago
$316
Roundtrip
found 12 hours ago
Sun, Jul 12 - Tue, Jul 21
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$893 Roundtrip, found 9 hours ago
$893
Roundtrip
found 9 hours ago
Discover Other Travel Deals
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- Van Buren State Park Vacations
- Fenn Valley Vineyards Vacations
- Kal Haven Trail Vacations