Wheeling Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Wheeling

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 S$312 per night from 29 Nov to 30 Nov
S$312
includes taxes & fees
29 Nov - 30 Nov
7.8/10 Good! (2,061 reviews)
"Everything is great"

Reviewed on 21 Nov,2024

Hilton Chicago O'Hare Airport
Chicago Getaway Hostel
Chicago Getaway Hostel
2 out of 5
616 W Arlington Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 25 Nov to 26 Nov
S$97
includes taxes & fees
25 Nov - 26 Nov
8.8/10 Excellent! (1,004 reviews)
"Would highly recommend"

Reviewed on 21 Nov,2024

Chicago Getaway Hostel
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
3 out of 5
6600 Mannheim Road, building 2, Rosemont, IL
Fully refundable
The price is S$152 per night from 26 Nov to 27 Nov
S$152
includes taxes & fees
26 Nov - 27 Nov
8.8/10 Excellent! (1,563 reviews)
"A nice airport hotel, however the restaurant closes at 9 pm for an international airport is shocking"

Reviewed on 22 Nov,2024

Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel
See all 2,338 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.

Frequently asked questions

How much does a Wheeling holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Wheeling from just . And the more you bundle, the more you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Wheeling?
Our Wheeling holiday packages mean plenty of savings for the savvy explorer. For the best deals, simply combine your flights, hotels and extras (such as activities) into a convenient package. But great bargains are only the start of your next unforgettable adventure. Book with Expedia and and you’ll have over 550 air carriers and 1,000,000 hotel options worldwide to pick from. Whatever your style, there’s a package to suit you.
Where should I stay in Wheeling?
A holiday in Wheeling isn’t complete without visiting Heritage Park, Prospect Heights City Hall and Rob Roy Golf Course. Spend your evenings near these popular attractions and make sightseeing easy.
What are the top hotels in Wheeling?
Get your escape off to a good start by reserving a room at Ramada Plaza by Wyndham Chicago North Shore. It’s one of most popular hotels in Wheeling. Another option is Olde Court Inn.
How far in advance should I book my Wheeling holiday?
The earlier, the better. Airlines usually release flight tickets up to a year in advance, and this is an excellent opportunity to pick up some of the lowest prices. Just been told you need to take all your holiday days in a few weeks? No need to worry. Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Wheeling travel package include?
With Expedia, you can choose a combination of hotels, flights and car rentals to build your perfect Wheeling package. Once you’ve made your booking, you can add on fun stuff like day tours and activities. Don’t forget — the more you bundle, the more dollars you’ll save!
What should I know before booking a Wheeling travel package?
We already have low prices. However, you’ll enjoy even more savings when you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and a great range of choice.
Can I choose my airline with a Wheeling Expedia holiday package?
Yes, so take your pick! Expedia has access to more than 550 partner airlines around the world, so you can customize your Wheeling getaway according to your budget and style.
If I'm not able to travel, can I cancel my Wheeling holiday package?
Yes, it’s possible to cancel your Wheeling booking if your plans have been upended. Whether you’ll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

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

Millennium Park

What to do in Wheeling

Flyover in Chicago

Flyover in Chicago

S$51
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$71
Per adult
94% of travellers recommend
Architecture River Tour
Narrated by certified, local docent

Chicago Architecture Center River Cruise aboard Chicago's First Lady

S$71
Per adult
98% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
See all activities in Wheeling

* 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.