Wheeling Vacation Packages

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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 Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,434, price is now CA $812 per person
CA $812
per person
Nov 8 - Nov 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Boutique hotel in downtown Chicago. Up to date facility, clean, quiet, good location.

Reviewed on Aug. 22, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was CA $1,426, price is now CA $833 per person
CA $833
per person
Oct 2 - Oct 7
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Close to walk most places. Lots of restaurants in the surrounding area. Staff very nice. Rooms clean and spacious.

Reviewed on Aug. 22, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $2,222, price is now CA $1,304 per person
CA $1,304
per person
Nov 8 - Nov 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,159 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

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,804, price is now CA $1,710 per person
CA $1,710
per person
Nov 8 - Nov 13
found 1 day ago
Roundtrip flight included
Edmonton (YEG) 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

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,636, price is now CA $1,008 per person
CA $1,008
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Ready to book your vacation to Wheeling?

 

Choose your dates

Wheeling Hotel Deals

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
The price is CA $198 per night from Sep 6 to Sep 7
CA $198
CA $232 total
Sep 6 - Sep 7
includes taxes & fees
8.4/10 Very Good! (1,123 reviews)
"Great amenities and very clean and friendly staff"

Reviewed on Aug. 20, 2025

Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Sep 12 to Sep 13
CA $248
CA $291 total
Sep 12 - Sep 13
includes taxes & 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

Hilton Chicago O'Hare Airport
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
The price is CA $198 per night from Sep 19 to Sep 20
CA $198
CA $225 total
Sep 19 - Sep 20
includes taxes & fees
8.6/10 Excellent! (1,884 reviews)
"Happy"

Reviewed on Aug. 22, 2025

Hyatt Regency O'Hare Chicago
See all 2,516 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.
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Discover the most popular places to visit in Wheeling

Wrigley Field featuring central business district, a city and a sporting event

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 which includes signage, a city and night scenes

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

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

CA $57
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Wheeling

Frequently asked questions

How much does a Wheeling vacation package cost?
You can pick up a vacation package to this top destination from CA $812 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.