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 Express Chicago NW - Arlington Heights by IHG
per person
Jul 23 - Jul 28
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Woodfield Mall and Allstate Arena are located nearby.

La Banque Hotel
Save 100% on your flight
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star 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.

Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. 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 Clark Street Beach and Halim Time & Glass Museum are located nearby.

Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star 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.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

Graduate by Hilton Evanston
Downtown Evanston
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Baha'i House of Worship and Aragon Ballroom are located nearby.

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool 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 ...

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 ...

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 ...
Save an average of 15% on thousands of hotels when you're signed in

Postcard Cabins Barber Creek
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 ...

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 ...

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. ...

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 ...

Lake Bluff Inn and Suites
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 ...
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.

Wed, Jun 11 - Wed, Jun 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago

Thu, Jun 5 - Wed, Jun 11
LAX
Los Angeles Intl.
MDW
Midway Intl.
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago

Sat, Jun 7 - Tue, Jun 10
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$293 Roundtrip, found 3 days ago
$293
Roundtrip
found 3 days ago

Tue, Jun 17 - Wed, Jul 9
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$408 Roundtrip, found 7 hours ago
$408
Roundtrip
found 7 hours ago
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