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Hollywood Casino Vacation Packages

Hollywood Casino 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 1 day 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 23 - Jul 27
found 24 hours 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.
DayDreamer Domes

DayDreamer Domes

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in South Haven. Enjoy free parking, room service, and onsite spa services. Popular attractions Kal Haven Trail and Michigan Maritime Museum are located nearby.
Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

4 out of 5
Save 100% on your flight
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Woodfield Mall and Allstate Arena are located nearby.
Hilton Garden Inn Chicago North Shore/Evanston

Hilton Garden Inn Chicago North Shore/Evanston

3.5 out of 5
Save 100% on your flight
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Washington (IAD) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Baha'i House of Worship and Aragon Ballroom are located nearby.
The Glen Club

The Glen Club

3.5 out of 5
per person
Jul 2 - Jul 6
found 21 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3.5-star golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and Kohl Children's Museum are located nearby.
Hyatt Centric Chicago Ohare

Hyatt Centric Chicago Ohare

3.5 out of 5
Save 100% on your flight
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rivers Casino are located nearby.
Crowne Plaza Lombard Downers Grove by IHG

Crowne Plaza Lombard Downers Grove by IHG

3.5 out of 5
per person
Jul 23 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Glen Ellyn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Lilacia Park and Yorktown Shopping Center are located nearby.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Save 100% on your flight
per person
Jul 23 - Jul 28
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 restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Wolff's Flea Market are located nearby.
Hampton Inn Chicago/Naperville

Hampton Inn Chicago/Naperville

2.5 out of 5
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip flight included
Washington (IAD) to Chicago (ORD)
Book a stay at this business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex are located nearby.
Dorothy's

Dorothy's

3 out of 5
Save 100% on your flight
per person
Jul 23 - Jul 27
found 19 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3-star B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

3 out of 5
per person
Jul 2 - Jul 6
found 20 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.

3-4 Night Vacations in Hollywood Casino

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

3.5 out of 5
per person
Jul 2 - Jul 6
found 21 hours ago
Roundtrip flight included
Houston (IAH) 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 3 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
DayDreamer Domes

DayDreamer Domes

4 out of 5
Save 100% on your flight
per person
Jul 2 - Jul 6
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

5-7 Night Vacations in Hollywood Casino

Price found within the past 48 hours. Click for updated prices.
The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 10 - Jul 15
found 17 hours ago
Roundtrip flight included
Houston (IAH) 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 4 - Jul 11
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 11
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 4 - Jul 11
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

Hollywood Casino Last Minute Hotel Deals

Motel 6 Naperville, IL
Motel 6 Naperville, IL
2 out of 5
1585 Naperville Wheaton Road, Naperville, IL
Stay at this motel in Naperville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Motel 6 Naperville, IL
Best Western Naperville Inn
Best Western Naperville Inn
2.5 out of 5
1617 Naperville Wheaton Rd, Naperville, IL
Book a stay at this eco-certified hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Best Western Naperville Inn
DoubleTree by Hilton Lisle Naperville
DoubleTree by Hilton Lisle Naperville
4 out of 5
3003 Corporate West Dr, Naperville, IL
Stay at this 4-star business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
DoubleTree by Hilton Lisle Naperville
Best Western Chicago - Downers Grove
Best Western Chicago - Downers Grove
2.5 out of 5
3010 Finley Rd, Downers Grove, IL
Book a stay at this business-friendly hotel in Downers Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Chicago - Downers Grove
Homewood Suites By Hilton Downers Grove Chicago, Il
Homewood Suites By Hilton Downers Grove Chicago, Il
3 out of 5
1500A Opus Place, Downers Grove, IL
Stay at this 3-star business-friendly hotel in Downers Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Homewood Suites By Hilton Downers Grove Chicago, Il
SureStay Plus Hotel by Best Western Chicago Lombard
SureStay Plus Hotel by Best Western Chicago Lombard
2.5 out of 5
222 E 22nd Street, Lombard, IL
Book a stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
SureStay Plus Hotel by Best Western Chicago Lombard
Crowne Plaza Lombard Downers Grove by IHG
Crowne Plaza Lombard Downers Grove by IHG
3.5 out of 5
1250 Roosevelt Road, Glen Ellyn, IL
Stay at this 3.5-star business-friendly hotel in Glen Ellyn. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in ...
Crowne Plaza Lombard Downers Grove by IHG
The Westin Chicago Lombard
The Westin Chicago Lombard
4 out of 5
70 Yorktown Center, Lombard, IL
Stay at this 4-star business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
The Westin Chicago Lombard
See all 1,505 properties in Hollywood Casino
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.