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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $521, price is now $343 per person
$343
per person
Jun 15 - Jun 17
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 $1,247, price is now $810 per person
$810
per person
Jul 2 - Jul 5
found 23 hours 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,049, price is now $711 per person
$711
per person
Jul 9 - Jul 12
found 22 hours 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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $868, price is now $595 per person
$595
per person
Jul 2 - Jul 5
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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.
The Wade

The Wade

4.5 out of 5
Save 100% on your flight
Price was $1,632, price is now $1,139 per person
$1,139
per person
Jun 18 - Jun 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier 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 $1,767, price is now $1,252 per person
$1,252
per person
Jun 18 - Jun 23
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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,774, price is now $1,257 per person
$1,257
per person
Jun 18 - Jun 23
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.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $752, price is now $539 per person
$539
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $646, price is now $421 per person
$421
per person
Jul 2 - Jul 5
found 1 day 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 $954, price is now $557 per person
$557
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,099, price is now $714 per person
$714
per person
Jul 9 - Jul 12
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 $1,247, price is now $810 per person
$810
per person
Jul 2 - Jul 5
found 23 hours 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,411, price is now $768 per person
$768
per person
Jul 22 - Jul 27
found 1 day 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 $1,540, price is now $834 per person
$834
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,553, price is now $918 per person
$918
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,620, price is now $999 per person
$999
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$201 Roundtrip, found 10 hours ago
$201
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $201 found 10 hours ago
Bargain Flight
Tue, Jul 28 - Tue, Aug 11
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Jul 28 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Tue, Aug 11, priced at $204 found 2 days ago
Bargain Flight
Thu, Aug 13 - Tue, Aug 18
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Aug 13 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Tue, Aug 18, priced at $237 found 1 day ago
Frontier Airlines
Tue, Jul 28 - Thu, Aug 13
DEN
Denver Intl.
MSN
Dane County Regional
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 28 from Denver Intl. to Dane County Regional, returning Thu, Aug 13, priced at $238 found 2 days ago