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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 $358, price is now $235 per person
$235
per person
Dec 11 - Dec 14
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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $676, price is now $404 per person
$404
per person
Dec 12 - Dec 16
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.
I’m a big guy so the shower was really small but other than that. The hotel was real good. 👍

Reviewed on Oct 11, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,068, price is now $647 per person
$647
per person
Dec 20 - Dec 26
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.
The staff is super nice and great amenities

Reviewed on Oct 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $949, price is now $590 per person
$590
per person
Dec 31 - Jan 5
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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $531, price is now $339 per person
$339
per person
Dec 11 - Dec 14
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 MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Save 100% on your flight
Price was $428, price is now $274 per person
$274
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $659, price is now $434 per person
$434
per person
Dec 17 - Dec 20
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.

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $742, price is now $497 per person
$497
per person
Nov 19 - Nov 22
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.
Very clean, well maintained, & the staff were extremely helpful.

Reviewed on Oct 10, 2026

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 $428, price is now $274 per person
$274
per person
Dec 12 - Dec 16
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 $676, price is now $404 per person
$404
per person
Dec 12 - Dec 16
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 $531, price is now $339 per person
$339
per person
Dec 11 - Dec 14
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 $697, price is now $453 per person
$453
per person
Dec 3 - Dec 6
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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $949, price is now $590 per person
$590
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,059, price is now $1,190 per person
$1,190
per person
Nov 12 - Nov 17
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) 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 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,068, price is now $647 per person
$647
per person
Dec 20 - Dec 26
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
Sat, Nov 7 - Wed, Nov 11
MSP
Minneapolis - St. Paul Intl.
MSN
Dane County Regional
$228 Roundtrip, found 9 hours ago
$228
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Sat, Nov 7 from Minneapolis - St. Paul Intl. to Dane County Regional, returning Wed, Nov 11, priced at $228 found 9 hours ago
Bargain Flight
Tue, Dec 1 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$262 Roundtrip, found 3 hours ago
$262
Roundtrip
found 3 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 3 hours ago
Bargain Flight
Tue, Oct 20 - Tue, Oct 27
DCA
Ronald Reagan Washington National
MSN
Dane County Regional
$278 Roundtrip, found 8 hours ago
$278
Roundtrip
found 8 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 8 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