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 Talbott, Autograph Collection
Downtown Chicago
CA $1,051
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,221
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Breakfast is offered on-site for purchase. Definitely able to make a day out of your stay at Sable due to it being located on Navy Pier’s actual property. Lots of fun attractions and great for the entire family or a couples retreat! Very versatile. Will be booking again.
Reviewed on Aug 19, 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 $188
CA $214 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $332
CA $390 total
Sep 12 - Sep 13
includes taxes & fees
8.4/10 Very good! (2,423 reviews)
"Easy access to early am flight!"
Reviewed on Aug 19, 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
CA $224
CA $255 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (2,951 reviews)
"Wonderful stay, right across from the convention center"
Reviewed on Aug 18, 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)
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
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
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 $1,051 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.
