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.
Hyatt Regency Lisle near Naperville
Price was $387, price is now $289 per person
$289
per person
Feb 13 - Feb 18
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Lisle. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Four Columns at Morton Arboretum and Belmont Prairie Nature Preserve are located nearby.
Bluestar Motel
Price was $633, price is now $444 per person
$444
per person
Feb 14 - Feb 22
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this motel in Chicago Ridge. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Chicago Ridge Shopping Mall and PGN Jump N' Fun Entertainment are located nearby.
Hotel Lincoln
Lincoln Park
Price was $615, price is now $447 per person
$447
per person
Feb 10 - Feb 17
found 2 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 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.
Dorothy's
Lakeview
Price was $475, price is now $347 per person
$347
per person
Feb 14 - Feb 22
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Crowne Plaza Lombard Downers Grove by IHG
Price was $503, price is now $371 per person
$371
per person
Feb 13 - Feb 18
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Glen Ellyn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Yorktown Shopping Center and Morton Arboretum are located nearby.
La Banque Hotel
Price was $812, price is now $606 per person
$606
per person
Feb 11 - Feb 15
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Springhill Suites by Marriott Chicago Downtown/ River North
Downtown Chicago
Save 100% on your flight
Price was $557, price is now $381 per person
$381
per person
Mar 4 - Mar 8
found 9 hours 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 a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,377, price is now $946 per person
$946
per person
Feb 18 - Feb 22
found 12 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Chicago (ORD)
Book a stay at this 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.
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 ...
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 ...
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
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. ...
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 ...
Comfort Inn & Suites
8258 Arnt Blvd Watervliet MI
Stay at this hotel in Watervliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Glenn Meadow Bed and Breakfast
6846 114th Ave South Haven MI
Stay at this B&B in South Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Virtue Cider and Fenn Valley Vineyards are located ...
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 ...
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.
Tue, Mar 17 - Tue, Mar 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 3 days ago
$140
Roundtrip
found 3 days ago
Thu, Jan 22 - Mon, Jan 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Fri, Jan 9 - Sun, Jan 11
LAX
Los Angeles Intl.
RFD
Greater Rockford
$571 Roundtrip, found 4 days ago
$571
Roundtrip
found 4 days ago
Wed, Mar 4 - Mon, Mar 16
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,144 Roundtrip, found 1 day ago
$1,144
Roundtrip
found 1 day ago