Search Deals on
Pearl City Vacation Packages

Build your package with 2 more options

Pearl City Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $503, price is now $303 per person
$303
per person
Mar 5 - Mar 8
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, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $623, price is now $377 per person
$377
per person
Mar 5 - Mar 8
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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $597, price is now $362 per person
$362
per person
Feb 20 - Feb 22
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $578, price is now $353 per person
$353
per person
Mar 5 - Mar 8
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 United Center and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $622, price is now $381 per person
$381
per person
Mar 5 - Mar 8
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 rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
Price was $552, price is now $355 per person
$355
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue 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 $577, price is now $371 per person
$371
per person
Mar 5 - Mar 8
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.

Pearl City Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $503, price is now $303 per person
$303
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
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
Price was $830, price is now $477 per person
$477
per person
Feb 26 - Mar 1
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 $623, price is now $377 per person
$377
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Pearl City Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Save 100% on your flight
Price was $467, price is now $298 per person
$298
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $638, price is now $372 per person
$372
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $927, price is now $556 per person
$556
per person
Jan 14 - Jan 19
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $1,023, price is now $635 per person
$635
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Wed, Dec 24 - Mon, Jan 5
LAS
Harry Reid Intl.
MSN
Dane County Regional
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 24 from Harry Reid Intl. to Dane County Regional, returning Mon, Jan 5, priced at $197 found 1 day ago
American Airlines
Wed, Dec 31 - Thu, Jan 1
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$201 Roundtrip, found 3 days ago
$201
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Dec 31 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Thu, Jan 1, priced at $201 found 3 days ago
American Airlines
Thu, Dec 25 - Mon, Jan 5
DEN
Denver Intl.
RFD
Greater Rockford
$236 Roundtrip, found 6 days ago
$236
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Dec 25 from Denver Intl. to Greater Rockford, returning Mon, Jan 5, priced at $236 found 6 days ago
American Airlines
Tue, Feb 17 - Thu, Feb 19
LAS
Harry Reid Intl.
RFD
Greater Rockford
$238 Roundtrip, found 5 days ago
$238
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Feb 17 from Harry Reid Intl. to Greater Rockford, returning Thu, Feb 19, priced at $238 found 5 days ago