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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.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
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, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
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, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
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, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff 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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Inn on Sheridan

The Inn on Sheridan

3.5 out of 5
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Save 100% on your flight
per person
Aug 14 - Aug 17
found 12 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

5-7 Night Vacations in South Side

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Aug 26 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day 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, 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 ...
Baymont by Wyndham South Haven
Postcard Cabins Barber Creek

Postcard Cabins Barber Creek

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 ...
Postcard Cabins Barber Creek
Country Inn & Suites by Radisson, South Haven, MI

Country Inn & Suites by Radisson, South Haven, MI

2.5 out of 5
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 ...
Country Inn & Suites by Radisson, South Haven, MI
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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 ...
AmericInn by Wyndham Douglas/Saugatuck
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 ...
Lake 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. ...
Starlite Resort
Sun N Sand Resort

Sun N Sand Resort

2.5 out of 5
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 ...
Sun N Sand Resort
Holiday Inn Express South Haven by IHG

Holiday Inn Express South Haven by IHG

2.5 out of 5
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 ...
Holiday Inn Express South Haven by IHG
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.

Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 1 hour ago
$120
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $120 found 1 hour ago
American Airlines
Sat, Sep 20 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 4 days ago
$192
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 20 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $192 found 4 days ago
Frontier Airlines
Mon, Aug 11 - Tue, Aug 12
LAX
Los Angeles Intl.
MDW
Midway Intl.
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Aug 11 from Los Angeles Intl. to Midway Intl., returning Tue, Aug 12, priced at $250 found 1 day ago
TAP Portugal
Fri, Aug 22 - Sat, Sep 6
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$525 Roundtrip, found 14 hours ago
$525
Roundtrip
found 14 hours ago
Select TAP Portugal flight, departing Fri, Aug 22 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $525 found 14 hours ago