New Chicago Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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 Saint Clair- Magnificent Mile
Downtown Chicago
S$614
per person
21 Nov - 23 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
The room was very small. The espresso machine had no counter top to set it on. The toilet had a long red streak on it. The beds were fine but squeaky. Could hear noise from other rooms and the street, even on the 14th floor.
Reviewed on 14 Oct, 2026
Le Méridien Essex Chicago
Downtown Chicago
S$667
per person
21 Nov - 23 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Wonderful Stay ! Would love to come back to Chicago again just for this hotel. Staff went above and beyond and we appreciate the great stay !
Reviewed on 14 Oct, 2026
Sentral Michigan Avenue
Downtown Chicago
S$684
per person
21 Nov - 23 Nov
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (1,344 reviews)
We stayed here for 3 nights for the Chicago Marathon 2026, and while the location was fantastic, the overall hotel experience fell well short of expectations.
The Good:
Unbeatable Location: The biggest advantage of this hotel is its proximity to Grant Park. Being just a short walk from the marathon start and finish lines made race day logistics completely stress-free.
The Bad & Disappointing:
Closed Pool: We specifically selected and booked this hotel because of their great-looking pool. Unfortunately, the pool was closed for the entire 3-night duration of our stay. When we complained to the front desk, nobody offered any remedy, compensation, or gesture to make up for it, which was extremely disappointing.
Poor Kitchenware: The room included kitchen facilities, but the dishes provided were very limited, scratched, and visibly worn out/overused.
Other than that, the stay itself was just okay. However, given the lack of any support or remedy from staff regarding the closed pool, we likely wouldn't stay here again.
Reviewed on 14 Oct, 2026
Top hotels in New Chicago
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Fully refundableReserve now, pay when you stay
S$192
18 Oct - 19 Oct
includes taxes & fees
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
S$148
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
"Helpful staff Dining and bar was closed early. Breakfast was fine."
Reviewed on 15 Oct, 2026
Motel 6 Hammond, IN - Chicago Area
3840 179th St Hammond IN
S$89
21 Oct - 22 Oct
includes taxes & fees
6.6/10 (1,001 reviews)
"Our reservation was not honored they were sold out. But the staff was excellent to accommodate us"
Reviewed on 14 Oct, 2026
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?
You can snap up a holiday package to this destination from S$614 on Expedia. But how much your holiday to New Chicago costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to New Chicago?
January, February and September are great times to look for cheap New Chicago holiday packages. Travelling in quieter months means you can usually find lower prices on flights and hotels.
How many days is enough for New Chicago?
With a well-organised schedule, you can easily visit the top New Chicago sights in a handful of days. But if you prefer to discover hidden spots or go on day tours, consider booking your New Chicago holiday for longer.
How to find the best New Chicago package deals?
Begin your search for a New Chicago package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect New Chicago package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your New Chicago adventure off to a flying start.
Is it cheaper to book a New Chicago holiday as a package?
You can enjoy significant savings on your New Chicago escape by booking a personalised holiday package. Check the "Package" heading, then enter your travel dates and destination to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to New Chicago?
If you're considering 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 score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to New Chicago?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to New Chicago.
- Work out your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your hotel will likely be the biggest expense during your trip to New Chicago.
- Determine how many days away: Start by compiling a list of the attractions you'd like to get to in New Chicago. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalised 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.
