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South Suburbs Vacation Packages

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South Suburbs Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
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, 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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
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, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

3 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. 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
Save 100% on your flight
per person
Aug 3 - Aug 8
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
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.

South Suburbs Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 22 - Aug 25
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 26 - Aug 30
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

South Suburbs Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
per person
Aug 3 - Aug 8
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 25 - Jul 31
found 16 hours 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
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Jul 22 - Tue, Jul 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 1 hour ago
$140
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $140 found 1 hour ago
Delta
Mon, Jul 14 - Tue, Jul 15
LAX
Los Angeles Intl.
MDW
Midway Intl.
$256 Roundtrip, found 2 days ago
$256
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Jul 14 from Los Angeles Intl. to Midway Intl., returning Tue, Jul 15, priced at $256 found 2 days ago
Icelandair
Wed, Aug 27 - Tue, Sep 2
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$555 Roundtrip, found 3 days ago
$555
Roundtrip
found 3 days ago
Select Icelandair flight, departing Wed, Aug 27 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Sep 2, priced at $555 found 3 days ago
Delta
Thu, Jun 19 - Mon, Aug 4
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$966 Roundtrip, found 10 hours ago
$966
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Jun 19 from Hong Kong Intl. to O'Hare Intl., returning Mon, Aug 4, priced at $966 found 10 hours ago