
Pearl City Holidays from AU$2,184
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Pearl City Holiday Deals
Price found within the past 48 hours. Click for updated prices.

The Royal Sonesta Chicago River North
Downtown Chicago
Price was AU$3,172, price is now AU$2,184 per person
AU$2,184
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
I had an amazing experience here! The staff—from valet to front desk to restaurant—was incredibly courteous, and Nate at the bar was a standout! My room was spotless, housekeeping was proactive, and guest services were top-tier.
The area around the hotel is packed with restaurants, bars, and convenience stores—super walkable and fun.
Only two minor cons: the terrace closes at 10 PM (wish it stayed open later), and the pool was closed during my visit.
Still, this place blew me away. Highly recommend!
Reviewed on 31 Aug. 2025

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was AU$4,113, price is now AU$2,534 per person
AU$2,534
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug. 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,610, price is now AU$3,478 per person
AU$3,478
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug. 2025

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,537, price is now AU$3,571 per person
AU$3,571
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The hotel was amazing. The staff were friendly. There is so much to do in the area.
Reviewed on 30 Aug. 2025

Level Chicago – Old Town
Downtown Chicago
Price was AU$3,524, price is now AU$2,340 per person
AU$2,340
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug. 2025
Pearl City Holiday
Pearl City Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Population | 810 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Lake Le Aqua Na State Park, Winneshiek Playhouse and Freeport Art Museum |
Our pick of the best Pearl City Hotel Deals

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Pearl City
The price is AU$502 per night from 29 Sept to 30 Sept
AU$502
29 Sept - 30 Sept
includes taxes & fees

Savanna Inn & Suites
101 Valley View Drive, Savanna, IL
Fully refundableReserve now, pay when you stay
The price is AU$229 per night from 1 Sept to 2 Sept
AU$229
1 Sept - 2 Sept
includes taxes & fees

Baymont by Wyndham Freeport
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is AU$146 per night from 21 Sept to 22 Sept
AU$146
21 Sept - 22 Sept
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
More holiday ideas
Expedia's Latest Trends
Hotels
- Honolulu accommodation
- Sedona accommodation
- Park City accommodation
- Aspen accommodation
- Anaheim accommodation
- Charlottesville accommodation
- Downtown Chicago Accommodation
- Telluride accommodation
- Palm Springs accommodation
- San Diego accommodation
- Winnetka accommodation
- Monterey accommodation
- Near North Side Accommodation
Flights
Cars
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.