Wheeling Vacations from $238

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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!

The Latest Wheeling vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $468, price is now $238 per person
$238
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $531, price is now $280 per person
$280
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Location is excellent, roof top bonus and breakfast double plus.

Reviewed on Oct 8, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $620, price is now $333 per person
$333
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on Oct 7, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,509, price is now $820 per person
$820
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,402, price is now $1,381 per person
$1,381
per person
Nov 21 - Nov 27
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Awesome room amazing tub even better service

Reviewed on Oct 2, 2025

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Discover the most popular places to visit in Wheeling

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Wheeling

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Wheeling

Wheeling Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $164 total per night from Oct 29 to Oct 30
$164 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (2,044 reviews)
"nice"

Reviewed on Oct 7, 2025

Hyatt Regency O'Hare Chicago
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Oct 15 to Oct 16
$93 total
Oct 15 - Oct 16
Total with taxes and fees
8.8/10 Excellent! (2,269 reviews)
"Great price, great motel and staff was great."

Reviewed on Oct 2, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Oct 24 to Oct 25
$179 total
Oct 24 - Oct 25
Total with taxes and fees
8.4/10 Very Good! (1,157 reviews)
"Lake"

Reviewed on Oct 3, 2025

Marriott Chicago O'Hare
See all 2,554 properties in Wheeling
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.

Wheeling Essential Information

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

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Frequently asked questions

How much does a Wheeling vacation package cost?
Offering excellent value package deals from $238 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the right Wheeling vacation package for you.
  6. 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.