How much does a Wheeling vacation package cost?

Offering excellent value package deals from $544 on Expedia, you'll be surprised at how little a vacation to Wheeling costs! Our packages make travel planning easier and save you more.

What are the cheapest months to go to Wheeling?

March, November and December are great times to look for cheap Wheeling vacation packages. Choosing to travel in quieter periods means you can generally find lower prices on flights and hotels.

How many days is enough for Wheeling?

With a well-planned itinerary, you can easily visit the main Wheeling attractions in a few days. But if you'd like to discover hidden spots or go on day tours, consider booking your Wheeling vacation 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 vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations separately. Better still, you can personalize 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 vacation 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?

Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Wheeling. Plan your budget wisely: On top of the cost of your hotel, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Wheeling. Organize your Wheeling escape with our trip planning tool : Look for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Wheeling together. Decide how many days away: Start by listing all the activities and sights you want to get to in Wheeling. Then, estimate how long you'll need for each, including any travel time. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the right Wheeling vacation package for you. Book any activities or day trips: Here's the fun part — organizing everything you want to do and see. Check out some of the incredible things to do in Wheeling in Wheeling and book your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Wheeling vacation packages?

Your Wheeling getaway is meant to be an escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

Wheeling Vacation Packages 2025/2026 from $544

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!

The Latest Wheeling vacation packages

Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

Save 100% on your flight

$544

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (1,962 reviews)

I enjoyed my stay here

Reviewed on Aug 23, 2025

The Emily Hotel

Downtown Chicago

$641

per person

Oct 31 - Nov 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,182 reviews)

The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

$636

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,087 reviews)

I give this hotel five stars. A very clean atmosphere. The staff is amazing, the valet workers knew my name, but the best was when I opened that door and seen that window view. It was amazing, gorgeous absolutely beautiful!! I would definitely stay again and tell people what a great experience I had here!

Reviewed on Aug 24, 2025

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$718

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,316 reviews)

Exceptional hotel with ideal location and nice services.

Reviewed on Aug 23, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

$1,154

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,690 reviews)

This property is beautiful and located in a great area.

Reviewed on Aug 19, 2025

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Wheeling Hotel Deals

Marriott Chicago O'Hare

8535 West Higgins Road, Chicago, IL

Fully refundableReserve now, pay when you stay

$152 nightly

$179 total

Sep 19 - Sep 20

Total with taxes and fees

8.4/10 Very Good! (1,124 reviews)

"Great amenities and very clean and friendly staff"

Reviewed on Aug 20, 2025

Hilton Chicago O'Hare Airport

O'Hare International Airport, Chicago, IL

Fully refundableReserve now, pay when you stay

$179 nightly

$210 total

Sep 19 - Sep 20

Total with taxes and fees

8.2/10 Very Good! (2,096 reviews)

"Within walking distance of the tram station at O'Hare International Airport. The food in the restaurant was okay--nothing to write home about."

Reviewed on Aug 22, 2025

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave, Rosemont, IL

Fully refundableReserve now, pay when you stay

$143 nightly

$163 total

Sep 19 - Sep 20

Total with taxes and fees

8.6/10 Excellent! (1,890 reviews)

"Clean!"

Reviewed on Aug 23, 2025

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.

Things to do in and around Wheeling

Wheeling, Illinois, is a fantastic destination for families and outdoor enthusiasts alike, offering a blend of city-themed attractions and nature activities. Visitors can enjoy shopping at various malls and centers while also partaking in outdoor fun such as horseback riding and golf experiences. With its memorable activities, Wheeling provides a delightful vacation experience for everyone looking to explore the area's vibrant offerings.

Shopping

If you're up for a drive, Woodfield Mall, located 8 miles away, offers a vibrant shopping experience with entertainment options. Closer to home, Wolff's Flea Market, just 5 miles away, is perfect for unique finds, while LEGOLAND® Discovery Center, 9 miles away, is a fun stop for families.

Recreation

Experience the energetic atmosphere at Allstate Arena, just 9 miles from Wheeling, where you can catch exciting sports events. Indulge in the luxurious ambiance of Chevy Chase Country Club, located only 1 mile away. For relaxation, visit Heritage Park, a serene spot within Wheeling perfect for wellness and tranquility.

Adventure

Experience excitement at Xtreme Trampolines, an arcadeAdventureZone with high-energy activities for the whole family, located 2 miles from Wheeling. Enjoy splashes of fun at Rainbow Falls Waterpark, a vibrant waterpark 10 miles away, perfect for adventure and entertainment. Don't miss Orbit Skate Center, 5 miles away, for thrilling skating fun.

Nightlife

Wheeling's nightlife offers vibrant options like Kingston Mines and Blues on Halstead, both nightclubs 20 miles away, perfect for romance and live entertainment. For a fun twist, head to Dave & Buster's 22 miles away, where you can enjoy drinks and games in a lively atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Wheeling

Wheeling, Illinois, offers a fantastic mix of family-friendly activities and urban adventures. Visitors can explore modern colleges, relax at nearby beaches, or enjoy the lush landscapes of urban parks. Whether you're seeking cultural experiences or fun for the whole family, Wheeling has something for everyone. Don't miss out on top attractions like Oglebay Park and other local points of interest to make your vacation memorable.

Schaumburg Convention Center: Located 8 miles from Wheeling, this convention center is perfect for business travelers and event-goers alike. Its modern facilities host a variety of conferences, trade shows, and corporate events, all while providing a professional atmosphere that encourages networking and innovation.
Six Flags Great America: Situated 16 miles from Wheeling, this thrilling theme park is a family favorite, boasting roller coasters, water rides, and entertainment options. With attractions for all ages, it's a perfect spot for a fun-filled day of excitement and laughter.
Northwestern University: About 14 miles away, this prestigious university offers a vibrant urban atmosphere. Visitors can explore beautiful campus architecture, art galleries, and cultural events, all while enjoying the energetic vibe of a bustling college community.

Best time to go to Wheeling

The best time to visit Wheeling is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	23.7°F (-4.6°C)	Light Rain	Mostly	Average	Slightly Low
February	25.5°F (-3.6°C)	Light Rain	Mostly	Average	Slightly Low
March	37.4°F (3.0°C)	Light Rain	Mostly	Average	Average
April	46.8°F (8.2°C)	Light Rain	Mostly	Average	Average
May	58.5°F (14.7°C)	Light Rain	Mostly Sunny	Average	Average
June	68.5°F (20.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	73.6°F (23.1°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	72.7°F (22.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	66.2°F (19.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	53.6°F (12.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly High
November	40.8°F (4.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	31.3°F (-0.4°C)	Light Rain	Mostly	Slightly Low	Slightly Low

Tips to save on your trip to Wheeling

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Wheeling.
Consider traveling to Wheeling during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.