New Chicago Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

New Chicago Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel G San Francisco

Hotel G San Francisco

4 out of 5
Union Square
Price was S$1,550, price is now S$1,426 per person
S$1,426
per person
24 Aug - 26 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9.2/10 Wonderful! (1,000 reviews)

The Marker Union Square San Francisco

The Marker Union Square San Francisco

4 out of 5
Union Square
Price was S$1,594, price is now S$1,436 per person
S$1,436
per person
24 Aug - 26 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9.2/10 Wonderful! (1,422 reviews)
Great location, and some of the friendliest staff I have encountered in the recent past.

Reviewed on 22 Jul, 2026

San Francisco Airport Marriott Waterfront

San Francisco Airport Marriott Waterfront

4 out of 5
Ingold - Milldale
Price was S$1,685, price is now S$1,537 per person
S$1,537
per person
24 Aug - 26 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
8.8/10 Excellent! (1,212 reviews)
Location was great, very close and easy drive from the airport. There’s a Safeway, Trader Joes, In-N-Out, and other stuff not too far away. My main issue was the shower, after a long journey on the plane, i was looking forward to a shower before getting an early night. The shower water pressure was insane, it was like a pressure washer you’d use to clean your car. Usually the complaints are about the pressure being too low, not here, or at least not in my room. The dial only allows you to control the water temperature and not the pressure. The only other issue I had was with the car parking, I paid for the parking which was approx. $50 for one night and everytime I tried to get in and out using the keycard they gave me it didn’t work and I had to hit call for help on the machine and wait for someone to open the barrier. For the amount I paid, I didn’t expect these issues. If these aren’t going to be a concern to you then carry on.

Reviewed on 23 Jul, 2026

Club Quarters Hotel in San Francisco

Club Quarters Hotel in San Francisco

4 out of 5
Downtown San Francisco
Price was S$1,592, price is now S$1,455 per person
S$1,455
per person
24 Aug - 26 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
9/10 Wonderful! (3,345 reviews)
Good location. Walking distance to restaurants

Reviewed on 23 Jul, 2026

Larkspur Landing Extended Stay Suites South San Francisco

Larkspur Landing Extended Stay Suites South San Francisco

3 out of 5
The East Side
Price was S$1,578, price is now S$1,462 per person
S$1,462
per person
24 Aug - 26 Aug
found 1 day ago
Return direct flight included
Singapore (SIN) to San Francisco (SFO)
7.6/10 Good! (1,010 reviews)
Clean and comfortable easy

Reviewed on 22 Jul, 2026

Top hotels in New Chicago

Red Hawk Resort & Casino

Red Hawk Resort & Casino

4 out of 5
1 Red Hawk Pkwy Placerville CA
Fully refundableReserve now, pay when you stay
The price is S$268 per night from 27 Jul to 28 Jul
S$268
27 Jul - 28 Jul
includes taxes & fees
Red Hawk Resort & Casino
Best Western Amador Inn

Best Western Amador Inn

2.5 out of 5
200 S State Highway 49 Jackson CA
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 26 Jul to 27 Jul
S$121
26 Jul - 27 Jul
includes taxes & fees
Best Western Amador Inn
Kiota Inn & Event Center Sutter Creek, an Ascend Collection Hotel

Kiota Inn & Event Center Sutter Creek, an Ascend Collection Hotel

3 out of 5
271 Hanford St Sutter Creek CA
Fully refundable
The price is S$176 per night from 16 Aug to 17 Aug
S$176
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"This place was amazing 10 stars! Very clean and welcoming lobby. Outside was very well maintained. A quick ride in the elevator to the second floor and wa-la, walked into a beautiful and inviting room. Could barely hear our neighbors TV, but the hotel was complete silence at 9pm. The best thing was ..."

Reviewed on 22 Jul, 2026

Kiota Inn & Event Center Sutter Creek, an Ascend Collection Hotel
See all 215 properties in New Chicago
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 New Chicago holiday package cost?
Offering excellent value package deals from S$1,426 on Expedia, you'll be thrilled with how little a holiday to New Chicago costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to New Chicago?
If you're hoping to score a cheap New Chicago holiday package, consider visiting in January, February and November. You'll usually find better prices on flights and accommodation during these quieter months — ideal for budget-conscious travellers.
How many days is enough for New Chicago?
Usually, a handful of days is enough to explore the main sights during your New Chicago holiday. However, if you want to have time to rest or go on day trips, consider extending your trip.
How to find the best New Chicago package deals?
Bagging a cheap New Chicago package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable New Chicago package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a New Chicago holiday as a package?
You can enjoy significant savings on your New Chicago getaway by booking a customised holiday package. Click on the "Package" heading, then select your travel dates and destination to see some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to New Chicago?
If you're planning an impromptu New Chicago holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to New Chicago?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to New Chicago.
  2. Plan your budget wisely: On top of the cost of your hotel, you'll need to consider other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that could arise during your trip to New Chicago.
  3. Decide how long to go away for: Now that you're up to speed on New Chicago, you can work out the ideal length of your holiday. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a tailored New Chicago holiday package.

* 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.