Wheeling Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
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Your Wheeling Vacation
When you organize a vacation package to Wheeling, you can relax and enjoy your getaway knowing your travel plans are in order. Uncover the wonders of this vibrant city while staying in a neighborhood like Riverwoods, which is good for nature. A trip to Wheeling is a superb opportunity to sightsee. Be sure to visit big-name attractions such as Marriott Theatre, The Glen Club and Arlington International Racecourse. Stop daydreaming and start doing. Explore the wide range of options on Expedia today and put your Wheeling vacation plans into action!
Top Wheeling Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
CA $2,564
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class
Reviewed on Oct 1, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
CA $1,199
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
I stayed in a room at the back, every morning at 5:30 am trucks and dumpsters were moved, noise so loud it woke me up.
Was charged an amenity fee and there were really mo amenities. Breakfast sucked both days in first floor restaurant. Won't stay again.
Reviewed on Oct 1, 2026
The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,676
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
Ready to book your vacation to Wheeling?
Wheeling Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
CA $228
CA $260 total
Oct 19 - Oct 20
includes taxes & fees
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
CA $230
CA $270 total
Oct 30 - Oct 31
includes taxes & fees
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
CA $192
CA $219 total
Nov 1 - Nov 2
includes taxes & fees
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)
After visiting Heritage Park, make a plan to see the other sights and activities in Wheeling. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
What to do in Wheeling
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Wheeling vacation package cost?
You can pick up a vacation package to this top destination from CA $1,075 on Expedia. However, how much your vacation to Wheeling costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Wheeling?
If you'd like to book a cheap Wheeling vacation package, consider travelling in January, March and December. You'll generally find lower rates on airfares and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Wheeling?
We recommend planning a Wheeling vacation for at least 3 days. This will allow you plenty of time to tick off major attractions including Arlington International Racecourse and Kemper Lakes Golf Club, and check out neighbourhoods like Riverwoods and Bannockburn. You could even slot in a day trip or two from Wheeling.
How to find the best Wheeling package deals?
Use Expedia's filter tool to find some unbeatable Wheeling package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Wheeling package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Wheeling vacation as a package?
You can enjoy significant savings on your Wheeling escape by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Wheeling?
If you've got your Wheeling travel dates locked in, book as soon as you can to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Wheeling?
- Choose when to get away: Check your diary and pack your bags. Your favourite time of year and the available activities will also help you decide when to escape to Wheeling.
- Figure out your budget: Ensure you have enough money to pay for everything from transportation and food to activities and airfares. Your hotel will probably be the biggest expense during your trip to Wheeling.
- Decide how long to go away for: Now that you know more about Wheeling, you can work out the right length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Wheeling vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
