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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.
Comfort Suites Elgin Northwest

Comfort Suites Elgin Northwest

2.5 out of 5
Save 100% on your flight
Price was $388, price is now $267 per person
$267
per person
Dec 10 - Dec 14
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Elgin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Randall Oaks Golf Club and Cinemark West Dundee are located nearby.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,086, price is now $646 per person
$646
per person
Nov 6 - Nov 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 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.
It was great great great !

Reviewed on Sep 28, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,562, price is now $976 per person
$976
per person
Nov 28 - Dec 4
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 a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
👍

Reviewed on Sep 28, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $858, price is now $582 per person
$582
per person
Dec 10 - Dec 14
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

The Glen Club

The Glen Club

4 out of 5
Save 100% on your flight
Price was $592, price is now $406 per person
$406
per person
Dec 3 - Dec 7
found 17 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Book a stay at this golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and The Glen Town Center are located nearby.
I was looking for a place to stay near Wilmette while on business, and this will now be my go-to. It was a lovely place to stay; it had a restaurant/bar on site with great food for any meal, and there are shops and awesome restaurants close by. Will definitely stay here again when visiting the Chicago area!

Reviewed on Sep 22, 2026

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 $713, price is now $493 per person
$493
per person
Nov 13 - Nov 15
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.
Staff were amazing, helpful and accommodating.

Reviewed on Sep 25, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Save 100% on your flight
Price was $790, price is now $548 per person
$548
per person
Nov 30 - Dec 2
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, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Save 100% on your flight
Price was $1,046, price is now $726 per person
$726
per person
Dec 11 - Dec 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, breakfast (surcharge), 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.

Pearl City Vacation Packages 3-4 Night Stays

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
Save 100% on your flight
Price was $686, price is now $452 per person
$452
per person
Dec 10 - Dec 13
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 $1,013, price is now $681 per person
$681
per person
Dec 2 - Dec 6
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 $1,276, price is now $865 per person
$865
per person
Nov 25 - Nov 28
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 $858, price is now $582 per person
$582
per person
Dec 10 - Dec 14
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

Pearl City Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $937, price is now $575 per person
$575
per person
Dec 8 - Dec 13
found 18 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 $1,987, price is now $1,137 per person
$1,137
per person
Nov 28 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,029, price is now $600 per person
$600
per person
Dec 11 - Dec 17
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 $1,562, price is now $976 per person
$976
per person
Nov 28 - Dec 4
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, Nov 10 - Sat, Nov 14
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$227 Roundtrip, found 14 hours ago
$227
Roundtrip
found 14 hours ago
Select Bargain Flight flight, departing Tue, Nov 10 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Sat, Nov 14, priced at $227 found 14 hours ago
Bargain Flight
Tue, Dec 1 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Dec 1 from Hartsfield-Jackson Atlanta Intl. to Quad City Intl., returning Tue, Dec 8, priced at $232 found 2 days ago
Bargain Flight
Tue, Oct 20 - Tue, Oct 27
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$263 Roundtrip, found 2 days ago
$263
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Oct 20 from Ronald Reagan Washington National to Dane County Regional, returning Tue, Oct 27, priced at $263 found 2 days ago
Bargain Flight
Sat, Nov 14 - Tue, Nov 17
BOS
Logan Intl.
MSN
Dane County Regional
$285 Roundtrip, found 5 hours ago
$285
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Sat, Nov 14 from Logan Intl. to Dane County Regional, returning Tue, Nov 17, priced at $285 found 5 hours ago