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Pearl City Vacation Packages

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Pearl City Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $582, price is now $386 per person
$386
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,495, price is now $800 per person
$800
per person
Oct 28 - Nov 3
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.

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,624, price is now $1,028 per person
$1,028
per person
Oct 28 - Nov 3
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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,274, price is now $825 per person
$825
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,019, price is now $1,351 per person
$1,351
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.
Great Accommodations for a quick weekend. The gym was topnotch.

Reviewed on Aug 25, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,495, price is now $1,009 per person
$1,009
per person
Oct 27 - Nov 3
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 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Price was $1,067, price is now $731 per person
$731
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury 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.

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 $1,213 per person
$1,213
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) 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.
Amazing view, clean room, helpful staff!

Reviewed on Aug 25, 2026

Pearl City Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $582, price is now $386 per person
$386
per person
Oct 7 - Oct 10
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 $1,073, price is now $673 per person
$673
per person
Oct 28 - Nov 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 $1,179, price is now $750 per person
$750
per person
Oct 28 - Nov 1
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 $1,274, price is now $825 per person
$825
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)

Pearl City Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,495, price is now $800 per person
$800
per person
Oct 28 - Nov 3
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 $1,659, price is now $876 per person
$876
per person
Oct 28 - Nov 3
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 $1,838, price is now $1,029 per person
$1,029
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,549, price is now $923 per person
$923
per person
Oct 27 - Nov 3
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.

Bargain Flight
Tue, Dec 1 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$228 Roundtrip, found 12 hours ago
$228
Roundtrip
found 12 hours ago
Select Bargain Flight flight, departing Tue, Dec 1 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Tue, Dec 8, priced at $228 found 12 hours ago
Bargain Flight
Fri, Oct 30 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$245 Roundtrip, found 1 hour ago
$245
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Fri, Oct 30 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Fri, Nov 13, priced at $245 found 1 hour ago
Bargain Flight
Tue, Oct 20 - Tue, Oct 27
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$268 Roundtrip, found 1 hour ago
$268
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Tue, Oct 20 from Ronald Reagan Washington National to Dane County Regional, returning Tue, Oct 27, priced at $268 found 1 hour ago
Bargain Flight
Tue, Sep 22 - Tue, Sep 29
BOS
Logan Intl.
MSN
Dane County Regional
$274 Roundtrip, found 5 days ago
$274
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Tue, Sep 22 from Logan Intl. to Dane County Regional, returning Tue, Sep 29, priced at $274 found 5 days ago