Wheeling Holidays from AU$4,460

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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.

The Latest Wheeling Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$4,903, price is now AU$4,460 per person
AU$4,460
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was AU$5,255, price is now AU$4,702 per person
AU$4,702
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$5,188, price is now AU$4,677 per person
AU$4,677
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$4,938, price is now AU$4,481 per person
AU$4,481
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)
Very beautiful room with great view... no complaints

Reviewed on 1 Nov 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was AU$4,858, price is now AU$4,470 per person
AU$4,470
per person
5 Jan - 11 Jan
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
Fantastic location and facility. Comfortable bed and nice shower! Perfect hotel for the Bears Game!

Reviewed on 1 Nov 2026

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

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$339 per night from 27 Nov to 28 Nov
AU$339
27 Nov - 28 Nov
includes taxes & fees
Hilton Chicago O'Hare Airport
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$239 per night from 25 Nov to 26 Nov
AU$239
25 Nov - 26 Nov
includes taxes & fees
8.6/10 Excellent! (1,451 reviews)
"Everything perfect"

Reviewed on 2 Nov 2026

Marriott Chicago O'Hare
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$274 per night from 22 Nov to 23 Nov
AU$274
22 Nov - 23 Nov
includes taxes & fees
9/10 Wonderful! (3,301 reviews)
"The room was clean and the staff was very helpful"

Reviewed on 2 Nov 2026

Hyatt Regency O'Hare Chicago
See all 2,757 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

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.
See properties

What to do in Wheeling

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

AU$61
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Wheeling

Frequently asked questions

How much does a Wheeling holiday package cost?
Offering excellent value package deals from AU$4,460 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.