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Pleasant Home Vacation Packages

Pleasant Home Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 out of 5
Price was $493, price is now $377 per person
$377
per person
Mar 12 - Mar 16
found 24 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Stay at this aparthotel in Chicago. Enjoy a fitness center, concierge services, and premium bedding. Our guests praise the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,254, price is now $830 per person
$830
per person
Mar 13 - Mar 17
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 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $781, price is now $530 per person
$530
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $938, price is now $650 per person
$650
per person
Mar 13 - Mar 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,455, price is now $1,035 per person
$1,035
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Price was $757, price is now $575 per person
$575
per person
Mar 17 - Mar 21
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.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,063, price is now $808 per person
$808
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool 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
Price was $721, price is now $551 per person
$551
per person
Mar 17 - Mar 21
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, 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.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Price was $600, price is now $459 per person
$459
per person
Mar 17 - Mar 21
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 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $571, price is now $438 per person
$438
per person
Mar 8 - Mar 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $773, price is now $594 per person
$594
per person
Mar 17 - Mar 21
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.
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
Price was $629, price is now $485 per person
$485
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Chicago Riverwalk and Michigan Avenue are located nearby.

3-4 Night Vacations in Pleasant Home

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Zion by IHG

Holiday Inn Express & Suites Zion by IHG

2.5 out of 5
Price was $262, price is now $190 per person
$190
per person
Mar 11 - Mar 14
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $326 per person
$326
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $938, price is now $650 per person
$650
per person
Mar 13 - Mar 17
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 $1,086, price is now $773 per person
$773
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,386, price is now $709 per person
$709
per person
Mar 14 - Mar 21
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
Price was $2,179, price is now $1,175 per person
$1,175
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,404, price is now $858 per person
$858
per person
Mar 14 - Mar 21
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 $1,296, price is now $820 per person
$820
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
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
See all 4,520 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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