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South Side Vacation Packages

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South Side Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Save 100% on your flight
Price was $575, price is now $348 per person
$348
per person
Jan 26 - Feb 2
found 3 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 free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,198, price is now $661 per person
$661
per person
Feb 14 - Feb 22
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,347, price is now $744 per person
$744
per person
Feb 14 - Feb 22
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, 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.
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
Save 100% on your flight
Price was $585, price is now $377 per person
$377
per person
Feb 14 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Arrowhead Golf Club are located nearby.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $755, price is now $494 per person
$494
per person
Jan 26 - Feb 2
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $551, price is now $361 per person
$361
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop 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.
SpringHill Suites by Marriott Chicago Naperville/Warrenville

SpringHill Suites by Marriott Chicago Naperville/Warrenville

3 out of 5
Save 100% on your flight
Price was $611, price is now $401 per person
$401
per person
Jan 26 - Feb 2
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Warrenville. Enjoy free breakfast, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cinemark Cantera Warrenville and Nike Sports Complex are located nearby.
Hotel Indigo Naperville Riverwalk by IHG

Hotel Indigo Naperville Riverwalk by IHG

3.5 out of 5
Save 100% on your flight
Price was $664, price is now $438 per person
$438
per person
Jan 26 - Feb 2
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dandelion Fountain and Riverwalk are located nearby.

3-4 Night Vacations in South Side

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $494, price is now $338 per person
$338
per person
Jan 25 - Jan 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $640, price is now $405 per person
$405
per person
Feb 20 - Feb 23
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $551, price is now $361 per person
$361
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $643, price is now $438 per person
$438
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in South Side

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $717, price is now $417 per person
$417
per person
Jan 26 - Feb 2
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $1,220, price is now $638 per person
$638
per person
Jan 26 - Feb 2
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $892, price is now $502 per person
$502
per person
Jan 26 - Feb 2
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $836, price is now $484 per person
$484
per person
Jan 26 - Feb 2
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Cheap Hotel Deals in South Side

Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
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 ...
Opens in a new windowBaymont by Wyndham South Haven
Old Harbor Inn

Old Harbor Inn

3 out of 5
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 ...
Opens in a new windowOld Harbor Inn
Captain's Quarters Motel

Captain's Quarters Motel

2 out of 5
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 ...
Opens in a new windowCaptain's Quarters Motel
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Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy

2 out of 5
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 ...
Opens in a new windowPostcard Cabins Barber Creek, Outdoor Collection by Marriott Bonvoy
Lake Bluff Inn and Suites

Lake Bluff Inn and Suites

2.5 out of 5
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 ...
Opens in a new windowLake Bluff Inn and Suites
Starlite Resort

Starlite Resort

2.5 out of 5
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. ...
Opens in a new windowStarlite Resort
Yelton Manor Bed & Breakfast

Yelton Manor Bed & Breakfast

3 out of 5
140 North Shore Drive South Haven MI
Stay at this B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Michigan Maritime Museum and Warner Vineyards are located ...
Opens in a new windowYelton Manor Bed & Breakfast
AmericInn by Wyndham Douglas/Saugatuck

AmericInn by Wyndham Douglas/Saugatuck

2 out of 5
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 ...
Opens in a new windowAmericInn by Wyndham Douglas/Saugatuck
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.

Frontier Airlines
Tue, Feb 10 - Wed, Feb 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 17 hours ago
$163
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Feb 10 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 18, priced at $163 found 17 hours ago
Frontier Airlines
Tue, Jan 13 - Thu, Jan 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Los Angeles Intl. to Midway Intl., returning Thu, Jan 15, priced at $192 found 1 day ago
Delta
Wed, Dec 31 - Thu, Jan 1
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$377 Roundtrip, found 2 days ago
$377
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Dec 31 from Los Angeles Intl. to Kalamazoo-Battle Creek Intl., returning Thu, Jan 1, priced at $377 found 2 days ago
American Airlines
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$439 Roundtrip, found 6 days ago
$439
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Jan 9 from Los Angeles Intl. to Greater Rockford, returning Sun, Jan 11, priced at $439 found 6 days ago