Search Deals onPearl City Vacation Packages
Pearl City Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Save 100% on your flight
Price was $673, price is now $426 per person
$426
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Four Seasons Hotel Chicago
Price was $4,670, price is now $2,475 per person
$2,475
per person
Sep 13 - Sep 19
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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,397, price is now $856 per person
$856
per person
Sep 25 - Sep 29
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.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
Price was $769, price is now $489 per person
$489
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
fabulous location and helpful staff.
Reviewed on Aug 1, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,684, price is now $1,081 per person
$1,081
per person
Oct 9 - Oct 12
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.
Level Chicago – Old Town
Save 100% on your flight
Price was $1,258, price is now $817 per person
$817
per person
Sep 25 - Sep 29
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.
Level Chicago Fulton Market
Save 100% on your flight
Price was $1,035, price is now $731 per person
$731
per person
Oct 1 - Oct 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.
Comes with all the comforts of
Home.
Reviewed on Jul 29, 2026
Fairmont Chicago at Millennium Park
Save 100% on your flight
Price was $1,030, price is now $737 per person
$737
per person
Oct 1 - Oct 4
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 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.
Loved it
Reviewed on Aug 1, 2026
Pearl City Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Pearl City Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Oct 10 - Fri, Oct 23
DEN
Denver Intl.
MSN
Dane County Regional
$190 Roundtrip, found 5 days ago
$190
Roundtrip
found 5 days ago
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Sun, Aug 30 - Thu, Sep 3
LAX
Los Angeles Intl.
MSN
Dane County Regional
$255 Roundtrip, found 6 days ago
$255
Roundtrip
found 6 days ago
Sat, Nov 14 - Mon, Nov 16
BOS
Logan Intl.
MSN
Dane County Regional
$260 Roundtrip, found 5 days ago
$260
Roundtrip
found 5 days ago
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