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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $342, price is now $216 per person
$216
per person
Dec 8 - Dec 12
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.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $702, price is now $418 per person
$418
per person
Dec 8 - Dec 12
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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $755, price is now $467 per person
$467
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Place was great in general 10/10 will be back

Reviewed on Oct 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $661, price is now $416 per person
$416
per person
Dec 18 - Dec 22
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.
The Riu was great. I especially liked their attention to low-energy use. And, yes, like other commenters stated, the breakfast was plentiful.

Reviewed on Oct 12, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $833, price is now $552 per person
$552
per person
Dec 3 - Dec 6
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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $998, price is now $670 per person
$670
per person
Dec 18 - Dec 22
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.

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 $795, price is now $541 per person
$541
per person
Dec 18 - Dec 22
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.

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 $471, price is now $325 per person
$325
per person
Dec 8 - Dec 12
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.

Pearl City Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $544, price is now $316 per person
$316
per person
Dec 8 - Dec 12
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 $620, price is now $362 per person
$362
per person
Dec 8 - Dec 12
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 $702, price is now $418 per person
$418
per person
Dec 8 - Dec 12
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 $755, price is now $467 per person
$467
per person
Dec 18 - Dec 22
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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $827, price is now $428 per person
$428
per person
Dec 14 - Dec 21
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 $936, price is now $538 per person
$538
per person
Dec 14 - Dec 21
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 $1,599, price is now $927 per person
$927
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,307, price is now $793 per person
$793
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Bargain Flight flight, departing Tue, Nov 10 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Sat, Nov 14, priced at $228 just found
Bargain Flight
Tue, Dec 1 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$262 Roundtrip, found 2 hours ago
$262
Roundtrip
found 2 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 $262 found 2 hours ago
Bargain Flight
Tue, Oct 20 - Tue, Oct 27
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$278 Roundtrip, found 7 hours ago
$278
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Ronald Reagan Washington National to Dane County Regional, returning Tue, Oct 27, priced at $278 found 7 hours ago
Bargain Flight
Mon, Nov 2 - Fri, Nov 13
ATL
Hartsfield-Jackson Atlanta Intl.
MSN
Dane County Regional
$286 Roundtrip, found 16 hours ago
$286
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Mon, Nov 2 from Hartsfield-Jackson Atlanta Intl. to Dane County Regional, returning Fri, Nov 13, priced at $286 found 16 hours ago