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Highland Vacation Packages

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Highland Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Chicago - Joliet

Red Roof Inn Chicago - Joliet

2 out of 5
per person
Mar 26 - Mar 29
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (CHI)
Stay at this hotel in Joliet. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Route 66 Raceway and Billie Limacher Bicentennial Park are located nearby.
Staybridge Suites, Lincolnshire, an IHG Hotel

Staybridge Suites, Lincolnshire, an IHG Hotel

3 out of 5
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Lincolnshire. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Marriott Theatre and Edward L. Ryerson Conservation Area are located nearby.
Harrah's Joliet Casino & Hotel

Harrah's Joliet Casino & Hotel

3.5 out of 5
per person
Mar 26 - Mar 29
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (CHI)
Stay at this 3.5-star business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

4 out of 5
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Rosemont. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Parkway Bank Park Entertainment District are located nearby.
Quality Inn Ottawa near Starved Rock State Park

Quality Inn Ottawa near Starved Rock State Park

2.5 out of 5
per person
Mar 26 - Mar 29
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Dayton Ridge Golf Club and Appellate Court are located nearby.
Super 8 by Wyndham Joliet I-55 N/Chicago

Super 8 by Wyndham Joliet I-55 N/Chicago

2 out of 5
per person
Mar 26 - Mar 29
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (CHI)
Book a stay at this business-friendly motel in Joliet. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Harrah's Casino and Westfield Louis Joliet Shopping Mall are located nearby.
Aloft Bolingbrook

Aloft Bolingbrook

3 out of 5
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Bolingbrook. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Promenade Bolingbrook and Boughton Ridge Golf Course are located nearby.
Hollywood Casino Joliet

Hollywood Casino Joliet

3 out of 5
per person
Mar 26 - Mar 29
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (CHI)
Stay at this 3-star resort in Joliet. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the property condition in our reviews. Popular attractions Route 66 Raceway and Hollywood Casino Joliet are located nearby.

Top Flight Deals

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

Spirit Airlines
Thu, Mar 20 - Tue, Mar 25
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Mar 20 from Los Angeles Intl. to O'Hare Intl., returning Tue, Mar 25, priced at $77 found 1 day ago
Frontier Airlines
Thu, May 8 - Sat, May 17
LAX
Los Angeles Intl.
MDW
Midway Intl.
$120 Roundtrip, found 4 days ago
$120
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 8 from Los Angeles Intl. to Midway Intl., returning Sat, May 17, priced at $120 found 4 days ago
Icelandair
Thu, Mar 20 - Tue, Apr 1
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$597 Roundtrip, found 4 days ago
$597
Roundtrip
found 4 days ago
Select Icelandair flight, departing Thu, Mar 20 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $597 found 4 days ago
American Airlines
Fri, Feb 28 - Mon, Mar 3
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,083 Roundtrip, found 1 day ago
$1,083
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Feb 28 from Pudong Intl. to O'Hare Intl., returning Mon, Mar 3, priced at $1,083 found 1 day ago