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Pleasant Home Vacation Packages

Pleasant Home Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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.
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
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per person
Jul 30 - Aug 4
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Dorothy's

Dorothy's

3 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 4
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, laundry facilities, and balconies or patios. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star aparthotel in Chicago. Enjoy free WiFi, laundry facilities, and premium TV channels. Popular attractions United Center and Grant Park are located nearby.
The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Save 100% on your flight
per person
Jul 30 - Aug 4
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, an outdoor pool, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

3-4 Night Vacations in Pleasant Home

Price found within the past 48 hours. Click for updated prices.
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
per person
Jul 31 - Aug 3
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 21 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) 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 16 - Jul 19
found 22 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)

5-7 Night Vacations in Pleasant Home

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 30 - Aug 4
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
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 30 - Aug 4
found 5 hours ago
Roundtrip flight included
Austin (AUS) 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 10 - Jul 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)

Pleasant Home Last Minute Hotel Deals

Carleton of Oak Park
Carleton of Oak Park
3 out of 5
1110 Pleasant St, Oak Park, IL
Stay at this 3-star boutique hotel in Oak Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our ...
Carleton of Oak Park
Harvey House Bed & Breakfast
Harvey House Bed & Breakfast
4 out of 5
107 South Scoville Avenue, Oak Park, IL
Stay at this 4-star B&B in Oak Park. Enjoy free breakfast, free WiFi, and free parking. Popular attractions United Center and Frank Lloyd Wright Historic District ...
Harvey House Bed & Breakfast
Travel Inn
Travel Inn
2.5 out of 5
1150 Roosevelt Rd, Broadview, IL
Stay at this motel in Broadview. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Frank Lloyd Wright Historic District and Drury ...
Travel Inn
The Shamrock
The Shamrock
2.5 out of 5
1212 S Cicero Ave, Cicero, IL
Stay at this motel in Cicero. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
The Shamrock
Cindy Lyn Motel
Cindy Lyn Motel
2 out of 5
5029 Ogden Ave, Cicero, IL
Stay at this motel in Cicero. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attractions United Center and SeatGeek Stadium are located ...
Cindy Lyn Motel
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
2.5 out of 5
200 S Mannheim Road, Hillside, IL
Book a stay at this business-friendly hotel in Hillside. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG
VIBE INN - WHIRLPOOL SUITES
VIBE INN - WHIRLPOOL SUITES
2.5 out of 5
7307 Ogden Ave, Lyons, IL
Stay at this motel in Lyons. Enjoy free parking, a 24-hour front desk, and cable TV channels. Popular attractions SeatGeek Stadium and Frank Lloyd Wright Historic ...
VIBE INN - WHIRLPOOL SUITES
Super 8 by Wyndham Chicago/Rosemont/O'Hare/SE
Super 8 by Wyndham Chicago/Rosemont/O'Hare/SE
2 out of 5
3160 North River Road, River & Belmont, River Grove, IL
Book a stay at this business-friendly motel in River Grove. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Super 8 by Wyndham Chicago/Rosemont/O'Hare/SE
See all 4,206 properties in Pleasant Home
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.

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