Pearl City Holidays

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Pearl City Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,105, price is now S$1,733 per person
S$1,733
per person
12 Oct - 19 Oct
found 11 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (2,288 reviews)
Chip painting in shower/tub

Reviewed on 22 Aug, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was S$2,898, price is now S$2,234 per person
S$2,234
per person
12 Oct - 19 Oct
found 11 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Proximity to all gates at airport

Reviewed on 23 Aug, 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
Price was S$2,301, price is now S$1,843 per person
S$1,843
per person
12 Oct - 19 Oct
found 11 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Not worth the price.

Reviewed on 21 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
Price was S$2,224, price is now S$1,802 per person
S$1,802
per person
12 Oct - 19 Oct
found 11 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.8/10 Excellent! (1,012 reviews)
It was a very nice place. I don’t agree with the parking fees and then the added on three dollar Eco fee when nursing to be parking right beside it that was the cities and didn’t seem like very of secure parking. It wasn’t fenced in or anything just I don’t understand the fee for the parking Other night. It was a stay

Reviewed on 24 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
Price was S$2,181, price is now S$1,844 per person
S$1,844
per person
12 Oct - 19 Oct
found 11 hours ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (2,393 reviews)
This time on 8th floor. Room is nicer and bed is firmer. The only issue is it's noisy due to cars "racing" on the road. The sound insulation may not as good, but not sure how other properties do

Reviewed on 24 Aug, 2025

Top hotels in Pearl City

Savanna Inn & Suites

Savanna Inn & Suites

2 out of 5
101 Valley View Drive, Savanna, IL
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 25 Aug to 26 Aug
S$183
25 Aug - 26 Aug
includes taxes & fees
9/10 Wonderful! (898 reviews)
"The rooms were clean just a little outdated. The toilet handle needed to be held a while to make it flush. Loved that it was pet friendly and that it was right near nice places for hiking. If you’re visiting galena it’s a cheaper place to stay still relatively close by. Breakfast was the same on ..."

Reviewed on 5 Aug, 2025

Savanna Inn & Suites
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 21 Sept to 22 Sept
S$111
21 Sept - 22 Sept
includes taxes & fees
6.8/10 (334 reviews)
"Local"

Reviewed on 16 Aug, 2025

Super 8 by Wyndham Freeport
Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is S$122 per night from 21 Sept to 22 Sept
S$122
21 Sept - 22 Sept
includes taxes & fees
8/10 Very Good! (679 reviews)
"Staff and service were great. Carpet and walls/trim on all floors were dirty and peeling. Overall a good stay."

Reviewed on 20 Aug, 2025

Baymont by Wyndham Freeport
See all 106 properties in Pearl City
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.

Frequently asked questions

How much does a Pearl City holiday package cost?
You'll find cheap prices from S$1,733 on Expedia for your Pearl City escape. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your holiday to Pearl City costs.
What are the cheapest months to go to Pearl City?
If you'd like to snag a cheap Pearl City holiday package, consider planning a trip in January, February and November. You'll typically find lower rates on accommodation and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Pearl City?
The ideal duration for your Pearl City holiday depends on what you'd like to see. Generally, a few days to a week will give you enough time to check out all the top sights and explore some hidden gems along the way.
How to find the best Pearl City package deals?
Use Expedia's filters to help you find some tempting Pearl City package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Pearl City package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Pearl City holiday as a package?
You can enjoy significant savings on your Pearl City getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Pearl City?
If you're planning an impromptu Pearl City adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Pearl City?

  1. Choose your dates: What you plan to do in Pearl City and your preferred season can help you decide when to go.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Pearl City.
  3. Decide how long to go away for: Now that you're up to speed on Pearl City, you can figure out the right length of your holiday. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Pearl City holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.