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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.
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
Save 100% on your flight
per person
Jun 18 - Jun 22
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex are located nearby.
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
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this eco-certified 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.
Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star business-friendly 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 Millennium Park and Art Institute of Chicago 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
Jun 29 - Jul 4
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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa 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 Millennium Park and Chicago Riverwalk are located nearby.

3-4 Night Vacations in South Side

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream

Hampton Inn Chicago-Carol Stream

2.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 23
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
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
Jun 30 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 23
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 30 - Jul 4
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.
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
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 29 - Jul 4
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
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
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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
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
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
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
Old Harbor Inn

Old Harbor Inn

3 out of 5
515 Williams Street, South Haven, MI
Stay at this 3-star hotel in South Haven. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean ...
Old Harbor Inn
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.

Frontier Airlines
Wed, May 28 - Sat, May 31
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 31, priced at $91 found 1 day ago
Frontier Airlines
Wed, May 28 - Tue, Jun 3
LAX
Los Angeles Intl.
MDW
Midway Intl.
$214 Roundtrip, found 11 hours ago
$214
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, May 28 from Los Angeles Intl. to Midway Intl., returning Tue, Jun 3, priced at $214 found 11 hours ago
Bargain Flight
Thu, Jun 26 - Sun, Jun 29
LAX
Los Angeles Intl.
SBN
South Bend Intl.
$367 Roundtrip, found 16 hours ago
$367
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Thu, Jun 26 from Los Angeles Intl. to South Bend Intl., returning Sun, Jun 29, priced at $367 found 16 hours ago
American Airlines
Wed, Jun 18 - Wed, Jul 9
LAX
Los Angeles Intl.
AZO
Kalamazoo-Battle Creek Intl.
$375 Roundtrip, found 6 days ago
$375
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jun 18 from Los Angeles Intl. to Kalamazoo-Battle Creek Intl., returning Wed, Jul 9, priced at $375 found 6 days ago