O'Hare Holidays
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
S$2,219
per person
8 Nov - 12 Nov
found 1 day ago
Return direct flight included
Singapore (SIN) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations.
Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay.
The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service.
This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨
Reviewed on 18 Sept, 2026
Where to stay in O'Hare
Find the best O'Hare areas and neighborhoods for the activities you enjoy most. Learn more about O'Hare
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in O'Hare
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
S$268
16 Oct - 17 Oct
includes taxes & fees
8.6/10 Excellent! (1,394 reviews)
"Everything was great!"
Reviewed on 17 Sept, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
S$337
17 Oct - 18 Oct
includes taxes & fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
S$260
20 Sept - 21 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.
Frequently asked questions
How much does an OHare holiday package cost?
Our OHare holiday packages, which begin from just S$854, are an awesome way to save big. All you have to do is choose your preferred hotels, flights and more to create your dream getaway.
How do I get a cheap travel package to OHare?
Lock in flights that fit your schedule, add a hotel room to your booking and watch the savings rack up with an OHare holiday package. It's as easy as that! From flights and hotels to activities and rental cars, Expedia makes travelling on the cheap easy. And with more than 550 airlines and 1,000,000 hotels around the globe to pick from, you won't be short of choice.
Where should I stay in OHare?
Cross Lincoln Park off your must-see list and then stay right around the corner. Experience the exciting vibe around this top attraction and head there whenever the mood strikes!
What are the top hotels in OHare?
Get your escape off to a fantastic start by booking a stay at O'Hare Inn & Suites. It's one of most sought-after hotels in OHare. Another cosy option is DoubleTree by Hilton Chicago OHare Airport - Rosemont.
How far in advance should I book my OHare holiday?
It can be hard to know when is the ideal time to book your trip to OHare. But generally the earlier you book, the cheaper the prices. Sometimes, you can lock in your flights and hotels nearly 12 months prior to your departure date. If you're thinking of a last-minute getaway, no need to panic! There are fabulous deals announced on Expedia every single day.
What does an Expedia OHare travel package include?
Rental cars, flights and hotels, or any combination of the three — it's your pick! Whether you're exploring OHare with the family or enjoying a solo break, there's a package to suit every budget and style. Once you've made your booking, why not add on some tours or activities?
What should I know before booking an OHare travel package?
We already have low prices. However, you'll score even better deals if you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and a huge range of choice.
Can I choose my airline with an OHare Expedia holiday package?
Definitely. Expedia has over 550 airline partners to choose from across the world. With such a big range of choice, finding the right carrier to get you to OHare won't be hard.
If I'm not able to travel, can I cancel my OHare holiday package?
If your holiday plans in OHare have been upended, it's comforting to know that it is possible to amend or cancel your booking. If you booked less than 24 hours ago, you may be able to get a refund. If your booking is older than that, your airline, hotel or car rental company may charge a cancellation fee. To find out more, check our Customer Service Portal.
Stay near popular O'Hare attractions
Grandparents Park
Grandparents Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or attend a sporting event in this vibrant area.
Cumberland Centre
You can take time to visit Cumberland Centre during your travels to Chicago. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Things to do
Skip the Line: Public Tour-Adult Admission Ticket (50 mins)
S$25
per adult
90% of travellers recommend
Rosemont: Two Flight Indoor Skydiving Experience
S$167
per traveller
The Infinite Wrench: Experimental theater in Chicago
S$25
per adult
* 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.