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.
Holiday Inn Chicago O'Hare – Rosemont by IHG
O'Hare
Save 100% on your flight
Price was $681, price is now $391 per person
$391
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,459, price is now $634 per person
$634
per person
Oct 22 - Oct 27
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.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,419, price is now $825 per person
$825
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Save 100% on your flight
Price was $809, price is now $476 per person
$476
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,241, price is now $764 per person
$764
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,980, price is now $1,221 per person
$1,221
per person
Oct 22 - Oct 27
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.
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
Save 100% on your flight
Price was $815, price is now $516 per person
$516
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
The Godfrey Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,783, price is now $1,206 per person
$1,206
per person
Oct 12 - Oct 19
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, a rooftop terrace, 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.
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 ...
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 ...
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 ...
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 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 ...
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 ...
Sun N Sand Resort
176 N. Blue Star Highway, South Haven, MI
Stay at this resort in South Haven. Enjoy free parking, daily housekeeping, and a picnic area. Our guests praise the helpful staff in our reviews. Popular attractions ...
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. ...
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 ...
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, Sep 13 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 5 days ago
$127
Roundtrip
found 5 days ago
Thu, Sep 25 - Sun, Sep 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$179 Roundtrip, found 3 hours ago
$179
Roundtrip
found 3 hours ago
Mon, Oct 6 - Sat, Oct 11
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Wed, Nov 5 - Wed, Nov 12
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$368 Roundtrip, found 15 hours ago
$368
Roundtrip
found 15 hours ago
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- Van Buren State Park Vacations
- Saugatuck-Douglas Historical Society Vacations
- Saugatuck Center For the Arts Vacations
- Kal Haven Trail Vacations
- 12 Corners Vineyards Vacations
