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Pleasant Home Vacation Packages

Pleasant Home Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $326, price is now $230 per person
$230
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Price was $378, price is now $253 per person
$253
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $410, price is now $275 per person
$275
per person
Jan 14 - Jan 19
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour 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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $982, price is now $572 per person
$572
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $424, price is now $276 per person
$276
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Chicago

Hilton Chicago

4 out of 5
Save 100% on your flight
Price was $463, price is now $317 per person
$317
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,018, price is now $703 per person
$703
per person
Jan 15 - Jan 19
found 20 hours ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $515, price is now $357 per person
$357
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue 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
Price was $863, price is now $605 per person
$605
per person
Jan 15 - Jan 19
found 20 hours ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this 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.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Save 100% on your flight
Price was $455, price is now $320 per person
$320
per person
Jan 15 - Jan 19
found 20 hours ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $554, price is now $390 per person
$390
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $506, price is now $357 per person
$357
per person
Jan 15 - Jan 19
found 20 hours ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. 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.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Save 100% on your flight
Price was $325, price is now $220 per person
$220
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $602, price is now $400 per person
$400
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $804, price is now $538 per person
$538
per person
Feb 4 - Feb 7
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was $446, price is now $308 per person
$308
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Pleasant Home

Price found within the past 48 hours. Click for updated prices.
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Price was $378, price is now $253 per person
$253
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $982, price is now $572 per person
$572
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,420, price is now $832 per person
$832
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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
Price was $1,077, price is now $633 per person
$633
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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
Book a stay at this 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
Holiday Inn Express and Suites Chicago West Oak Park by IHG

Holiday Inn Express and Suites Chicago West Oak Park by IHG

2.5 out of 5
1140 Lake Street Oak Park IL
Stay at this hotel in Oak Park. Enjoy free breakfast. Popular attractions Frank Lloyd Wright Historic District and Walt Disney House are located nearby.
Holiday Inn Express and Suites Chicago West Oak Park by IHG
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4 out of 5
107 South Scoville Avenue Oak Park IL
Stay at this B&B in Oak Park. Enjoy free breakfast, free WiFi, and free parking. Popular attractions United Center and Frank Lloyd Wright Historic District are ...
Harvey House Bed & Breakfast
Historic Oak Park Home

Historic Oak Park Home

2 out of 5
421 N Oak Park Avenue Oak Park IL
Stay at this apartment in Oak Park. Enjoy a computer station and housekeeping. Popular attractions Frank Lloyd Wright Historic District and Walt Disney House ...
Historic Oak Park Home
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 Anna and Frederick Douglass ...
Cindy Lyn Motel
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 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 4,479 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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