Wheeling Vacation Packages 2026 from $343

Wheeling flight + hotel vacation packages

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

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

$343

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This smoke-free resort features a golf course, a full-service spa, and a water park. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 4 restaurants and free perks like free self parking and an area shuttle.

Destination Geneva National

Save 100% on your flight

$388

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A golf course, 5 restaurants, and an indoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 4 bars/lounges and enjoy perks like free self parking. You'll appreciate the gym, poolside bar, and snack bar/deli.

Le Méridien Essex Chicago

Downtown Chicago

Save 100% on your flight

$752

per person

Nov 24 - Nov 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, dry cleaning, and luggage storage are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

$981

per person

Nov 29 - Dec 2

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Grand Geneva Resort & Spa

Save 100% on your flight

$510

per person

Nov 13 - Nov 15

found 21 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This smoke-free resort features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

Top Wheeling hotels deals

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free Cancellation

Reserve now, pay when you stay

$234 nightly

$275 total

Sep 20 - Sep 21

Total with taxes and fees

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Free airport shuttle

Pet friendly

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Free Cancellation

Reserve now, pay when you stay

$187 nightly

$213 total

Oct 11 - Oct 12

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.

Free airport shuttle

Pet friendly

Marriott Chicago O'Hare

8535 West Higgins Road Chicago IL

Free Cancellation

Reserve now, pay when you stay

$178 nightly

$209 total

Sep 27 - Sep 28

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's an indoor pool on site, and a 24-hour front desk and a coffee shop are also provided.

Pool

Free airport shuttle

Holiday Inn Chicago North-Evanston by IHG

1501 Sherman Ave Evanston IL

Free Cancellation

$139 nightly

$159 total

Oct 12 - Oct 13

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-out are also offered.

Free WiFi

Restaurant

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

5440 N River Rd Rosemont IL

Free Cancellation

$161 nightly

$184 total

Sep 20 - Sep 21

Total with taxes and fees

This smoke-free hotel includes 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.

Pool

Free airport shuttle

DoubleTree by Hilton Chicago O'Hare Airport - Rosemont

5460 North River Road Rosemont IL

$147 nightly

$167 total

Sep 20 - Sep 21

Total with taxes and fees

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Valet parking, a coffee shop, and a snack bar/deli are also offered.

Free airport shuttle

Pet friendly

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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.

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Frequently asked questions

How much are vacation packages to Wheeling?

With vacation packages on offer from as little as $343, you won't need to max out the credit card for your trip to Wheeling. Travelocity can help. Bundle up experiences, hotels and flights into a convenient package and receive some exciting discounts. The more you book, the more you save.

How long should my Wheeling vacation be?

Most people secure a hotel for 3 nights in Wheeling. But that doesn't mean you're limited to that. How long you spend here boils down to what you hope to do on your vacation. If you intend to explore every corner of this superb location, consider staying another night or two (or even longer!).

Where can I get the best vacation package deals for Wheeling?

Travelocity is here to help you snap up an awesome Wheeling package deal. With no less than 400 air carriers and 1,000,000 properties across the globe, there's no doubt you'll find the perfect combination.

Why should I purchase my Wheeling vacation bundle with Travelocity?

Travel is all about making cherished new memories and forgetting all your worries — which is why we have a team of experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our superb range of destinations. So what are you waiting for? There's no time like the present to secure that vacation you've always wanted.

Can I save money on my Wheeling car rental if I book it with my hotel or flight?

You most certainly can — combine your flight, car and hotel into a Wheeling vacation package and you can save a handsome sum. With so much to discover in Wheeling, having your own set of wheels will make exploring a breeze. Once you're in the driver's seat, turn up the stereo and make your way to University of Wisconsin-Madison, an unmissable attraction about 100 mi from Wheeling.

Which airport is best for Wheeling?

O'Hare Intl. Airport (ORD) is 11 mi from the downtown area and is the starting point for many adventures. Alternatively, Midway Intl. Airport (MDW) is 25 mi away from central Wheeling and General Mitchell Intl. Airport (MKE) is 55 mi away from central Wheeling.

What is there to do in Wheeling?

Heritage Park is one of the outstanding sights that make Wheeling such a popular destination. But leave some extra time to experience the city's lesser-known attractions too. This is sometimes where the best memories are created.

Where should I stay when visiting Wheeling?

If you're after somewhere to spend your nights, check out the Ramada Plaza by Wyndham Chicago North Shore. It's the top choice for many travelers.