Search Deals onSouth Side Vacation Packages
South Side Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $736, price is now $508 per person
$508
per person
Nov 7 - Nov 11
found 20 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 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,748, price is now $1,013 per person
$1,013
per person
Nov 7 - Nov 11
found 20 hours 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 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 Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,000, price is now $634 per person
$634
per person
Nov 12 - Nov 16
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 a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,739, price is now $1,131 per person
$1,131
per person
Oct 28 - Nov 3
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.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
Price was $1,402, price is now $913 per person
$913
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,209, price is now $807 per person
$807
per person
Nov 7 - Nov 11
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,121, price is now $750 per person
$750
per person
Nov 12 - Nov 16
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 a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Wrigleyville Inn
Lakeview
Save 100% on your flight
Price was $1,358, price is now $941 per person
$941
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Wrigley Field 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 Upper Scott Lake are located ...
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 ...
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. ...
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 ...
Comfort Suites South Haven near I-96
1755 Phoenix Street South Haven MI
Book a stay at this business-friendly hotel in South Haven. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff 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 ...
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.
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Sun, Nov 8 - Thu, Nov 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200 Roundtrip, found 7 hours ago
$200
Roundtrip
found 7 hours ago
Tue, Sep 29 - Sat, Oct 10
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$484 Roundtrip, found 1 day ago
$484
Roundtrip
found 1 day ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,074 Roundtrip, found 1 day ago
$1,074
Roundtrip
found 1 day ago