Wheeling Holidays from NZ$3,258
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The Latest Wheeling Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
NZ$3,767
per person
14 Oct - 18 Oct
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on 2 Sept 2026
Level Chicago - River North
Downtown Chicago
NZ$3,588
per person
14 Oct - 18 Oct
found 17 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,064 reviews)
Such a great place to stay with your partner! It was the best decision. It was somewhat of a walk to riverwalk but you dont even notice. Plus- the views during sunset were unbeatable with the large view windows.
Reviewed on 2 Sept 2026
Wheeling Holiday
Our pick of the best Wheeling Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
NZ$530
27 Sept - 28 Sept
includes taxes & fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
NZ$346
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (3,105 reviews)
"Clean ,relaxing and helpful staff . Will be returning"
Reviewed on 3 Sept 2026
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
NZ$375
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (1,376 reviews)
"Staff friendly shuttle service was great"
Reviewed on 2 Sept 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.
Stay near popular Wheeling attractions
Heritage Park
6.8/10 (35 reviews)
Heritage Park offers 104 acres of recreation with a scenic lake, sports fields, and miles of walking paths. Enjoy bird-watching from the 1.3-mile lakeside trail or reserve a picnic shelter for family gatherings.
What to do in Wheeling
Frequently asked questions
How much does a Wheeling holiday package cost?
Offering excellent value package deals from NZ$3,258 on Expedia, you'll be surprised at how little a holiday to Wheeling costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Wheeling?
You can usually find lower prices and greater availability in January, March and December. Explore our cheap Wheeling holiday packages and you could get some great off-season discounts.
How many days is enough for Wheeling?
With a well-planned schedule, you can easily hit the main Wheeling sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Wheeling holiday for longer.
How to find the best Wheeling package deals?
Begin your search for a Wheeling package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Wheeling package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wheeling escape underway.
Is it cheaper to book a Wheeling holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and accommodation separately. Better still, you can personalise your Wheeling getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Wheeling?
If you've got your Wheeling travel dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Wheeling?
- Choose your travel dates: What you'd like to do in Wheeling and your favourite season can help you decide when to go.
- Budget wisely: As well as the price of your hotel, you should consider other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Wheeling.
- Decide how long to go for: Now that you're more familiar with Wheeling, you can figure out the perfect length of your break. Create a rough plan and give yourself enough time to cover everything you want to do.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Wheeling holiday package that brings all your bookings together.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
