How much does a Wheeling vacation package cost?

Offering excellent value package deals from $393 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 2026 from $393

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.

Hilton Chicago

Downtown Chicago

Save 100% on your flight

$393

per person

Apr 4 - Apr 8

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,301 reviews)

Staff members were friendly and helpful. Great location walking distance and transportation options.

Reviewed on Jan 9, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$446

per person

Apr 4 - Apr 8

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Great breakfast, Clean room, enjoyed the stay

Reviewed on Jan 9, 2026

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$469

per person

Apr 4 - Apr 8

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

Perfect location, comfortable and clean room

Reviewed on Jan 5, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

$526

per person

Apr 4 - Apr 8

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (317 reviews)

Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$538

per person

Apr 4 - Apr 8

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Don't see what you're looking for?

See all available trips from Columbus to Wheeling

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Wheeling Hotel Deals

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$196 nightly

$230 total

Feb 6 - Feb 7

Total with taxes and fees

8.2/10 Very Good! (2,177 reviews)

Great stay fir early flights

Reviewed on Jan 8, 2026

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Fully refundableReserve now, pay when you stay

$118 nightly

$135 total

Feb 1 - Feb 2

Total with taxes and fees

8.8/10 Excellent! (2,307 reviews)

Comfortable and elegant, the only thing missing was a free breakfast

Reviewed on Jan 6, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

5440 N River Rd Rosemont IL

Fully refundable

$105 nightly

$120 total

Jan 20 - Jan 21

Total with taxes and fees

8.6/10 Excellent! (2,685 reviews)

Overall the room was fine but there were insufficient blankets on the bed! Upped the room temp to 72 (and I'm used to 68 at home) and still used a bath towel as an added blanket!

Reviewed on Dec 31, 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 near Wheeling

Wheeling, Illinois, offers a variety of activities perfect for families and business travelers alike. Visitors can enjoy outdoor fun with golfing and horseback riding, while shopping enthusiasts can explore local shopping centers. Whether you're looking for memorable experiences or simply a day of relaxation, Wheeling has something for everyone to enjoy.

Shopping

In Wheeling, you can visit Wolff's Flea Market for unique finds just 5 miles away. If you're up for a drive, check out Woodfield Mall, 8 miles away, for a vast selection of shops and entertainment. LEGOLAND® Discovery Center is also nearby at 9 miles, perfect for family fun.

Recreation

Experience the thrill of live sports at Allstate Arena, just 9 miles from Wheeling. Enjoy a romantic evening at Marriott Theatre, 4 miles away, featuring captivating performances. For music lovers, Ravinia Pavilion, 8 miles distant, offers unforgettable concerts in a stunning outdoor setting.

Adventure

Xtreme Trampolines is an exhilarating arcadeAdventureZone located 2 miles from Wheeling, offering a thrilling atmosphere for family fun and adventure. Rainbow Falls Waterpark, situated 10 miles away, provides a splashy retreat with entertainment for all ages. Orbit Skate Center, 5 miles from Wheeling, is perfect for skating enthusiasts seeking excitement.

Nightlife

For a vibrant nightlife experience near Wheeling, check out Kingston Mines and Blues on Halstead, both 20 miles away, offering lively atmospheres with romance and city vibes. Dave & Buster's, located 22 miles away, combines entertainment with a pub setting, perfect for a fun night out.

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

Find the best attractions near Wheeling

Wheeling, Illinois, is perfect for family, business, and city-themed vacations, offering a mix of modern attractions. Visitors can explore local points of interest such as urban parks, beaches, and colleges, catering to those seeking cultural and family experiences. Don't miss top attractions like Oglebay Park and other tourist destinations that highlight the charm of this vibrant city.

Schaumburg Convention Center: Located 8 miles from Wheeling, this state-of-the-art venue buzzes with business vibes. It's perfect for conferences, trade shows, and exhibitions, featuring versatile spaces and modern amenities that cater to professional gatherings.
Six Flags Great America: About 16 miles away, this thrilling theme park offers a family-friendly atmosphere packed with entertainment. Expect exhilarating rides, live shows, and various attractions that ensure a fun-filled day for visitors of all ages.
Northwestern University: Situated 14 miles from Wheeling, this prestigious university boasts a vibrant city vibe. Explore its beautiful campus, impressive architecture, and engaging cultural events that reflect a rich academic environment.

Best time to go to Wheeling

The best time to visit Wheeling is dependent 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 cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	23.7°F (-4.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	25.5°F (-3.6°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	37.4°F (3.0°C)	Light Rain	Mostly Cloudy	Average	Average
April	46.8°F (8.2°C)	Light Rain	Mostly Cloudy	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 Cloudy	Slightly Low	Slightly Low

Tips to save on your trip to Wheeling

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
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.

Language	English
Currency	U.S dollars
Closest Airport	O'Hare Intl. Airport (ORD)
Population	38,100
Max Temp Winter	30ºF
Max Temp Summer	80ºF
Top Sights	Rosemont Theatre, Parkway Bank Park Entertainment District and Marriott Theatre

Language

English

Currency

U.S dollars

Closest Airport

O'Hare Intl. Airport (ORD)

Population

38,100

Max Temp Winter

30ºF

Max Temp Summer

80ºF