Wheeling Holidays

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Your Wheeling Holiday

Take the hassle out of travel planning by booking a Wheeling holiday package. A good neighbourhood to stay in this fascinating city is Riverwoods, which is good for nature and a lot more. Like to explore? The Glen Club, Marriott Theatre and Arlington International Racecourse are some of the top places to visit during a trip to Wheeling. Browse Expedia's extensive range of travel options and start planning your perfect holiday to Wheeling today.

Wheeling Holiday

Wheeling Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
38,100
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Marriott Theatre

Our pick of the best Wheeling Hotel Deals

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$261 per night from 6 Sept to 7 Sept
AU$261
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very Good! (1,124 reviews)
"Great amenities and very clean and friendly staff"

Reviewed on 20 Aug. 2025

Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$327 per night from 12 Sept to 13 Sept
AU$327
12 Sept - 13 Sept
includes taxes & fees
8.2/10 Very Good! (2,097 reviews)
"The room was clean and the bed was comfortable. The staff was courteous and helpful."

Reviewed on 18 Aug. 2025

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is AU$254 per night from 19 Sept to 20 Sept
AU$254
19 Sept - 20 Sept
includes taxes & fees
8.6/10 Excellent! (1,874 reviews)
"Quick service and got extra blankets with a simple text"

Reviewed on 21 Aug. 2025

Hyatt Regency O'Hare Chicago
See all 2,516 properties in Wheeling
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Wheeling

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Wheeling

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Wheeling

Frequently asked questions

How much does a Wheeling holiday package cost?
Offering excellent value package deals 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?

  1. Choose your travel dates: What you'd like to do in Wheeling and your favourite season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.