Wheeling Vacations from ￥346,933
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The Latest Wheeling Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
￥396,404
per person
Nov 14 - Nov 20
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,162 reviews)
Hotel was fine but it wasn’t up to par with other Pendry brand hotels I’ve stayed at. Mattresses were worn and you could feel digits from use. They should give earplugs & eyemasks to guests as drag cars race the streets allll night. There were lights in our headboard we couldn’t turn off. When we checked in they offered a house car to use, however in our 4 day span it was never available. It isn’t in service until noon and the driver always seemed to be on break. If I were them, I wouldn’t bother mentioning the amenity.
Reviewed on Sep 7, 2026
Find the Best Wheeling Vacation Packages
Wheeling Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
￥38,909
￥45,677 total
Sep 11 - Sep 12
includes taxes & fees
8.4/10 Very Good! (2,485 reviews)
"Excellent airport location. Very convenient access to all terminals, including the farthest T5. The staff was very friendly and knowledgeable. Restaurant couls use less AC - it was very cold my likeness."
Reviewed on Sep 7, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
￥29,377
￥33,485 total
Oct 4 - Oct 5
includes taxes & fees
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
￥29,393
￥34,505 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (1,393 reviews)
"."
Reviewed on Sep 8, 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
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,453
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
￥6,484
per adult
94% of travellers recommend
Frequently asked questions
How much does a Wheeling vacation package cost?
Offering excellent value package deals from ￥346,933 on Expedia, you'll be surprised at how little a vacation 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 vacation 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 vacation 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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations separately. Better still, you can personalize 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 vacation 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 favorite 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 vacation 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.
