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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.
Holiday Inn Express Chicago NW - Arlington Heights by IHG

Holiday Inn Express Chicago NW - Arlington Heights by IHG

2.5 out of 5
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

La Banque Hotel

4 out of 5
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

Hilton Orrington / Evanston

4 out of 5
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

Level Chicago - River North

4 out of 5
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

Trump International Hotel & Tower Chicago

5 out of 5
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

Graduate by Hilton Evanston

4 out of 5
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

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
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

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
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.
Hilton Garden Inn Naperville/Warrenville

Hilton Garden Inn Naperville/Warrenville

3 out of 5
per person
Jul 3 - Jul 6
found 9 hours ago
Roundtrip flight included
Orlando (MCO) 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
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 24 - Jul 28
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

5-7 Night Vacations in South Side

Price found within the past 48 hours. Click for updated prices.
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
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
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)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jul 3 - Jul 9
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
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)

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
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
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
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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
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
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
Comfort Suites South Haven near I-96

Comfort Suites South Haven near I-96

2.5 out of 5
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 ...
Comfort Suites South Haven near I-96
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
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
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
Select Spirit Airlines flight, departing Wed, Jun 11 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 11, priced at $112 found 1 day ago
Frontier Airlines
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
Select Frontier Airlines flight, departing Thu, Jun 5 from Los Angeles Intl. to Midway Intl., returning Wed, Jun 11, priced at $251 found 3 days ago
Bargain Flight
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
Select Bargain Flight flight, departing Sat, Jun 7 from Los Angeles Intl. to South Bend Intl., returning Tue, Jun 10, priced at $293 found 3 days ago
American Airlines
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
Select American Airlines flight, departing Tue, Jun 17 from Los Angeles Intl. to Kalamazoo-Battle Creek Intl., returning Wed, Jul 9, priced at $408 found 7 hours ago