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 Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,066 reviews)
nice services at all

Reviewed on Aug. 3, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Very friendly staff!

Reviewed on Aug. 3, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Great stay :) Mr 47 didn’t disappoint

Reviewed on Aug. 1, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,922 reviews)
We spent 4 nights and had no major complaints. I don't understand why there was an additional mandatory destination fee for normal amenities that we did not ask for or use.

Reviewed on Aug. 1, 2025

Ready to book your vacation to Wheeling?

 

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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
The price is CA $186 per night from Aug 24 to Aug 25
CA $186
CA $212 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (1,803 reviews)
"Excellent exce"

Reviewed on Jul. 31, 2025

Hyatt Regency O'Hare Chicago
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 $266 per night from Aug 31 to Sep 1
CA $266
CA $312 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (2,070 reviews)
US break
"Hotel is well run and organised, very friendly staff and superb facilities. Buffet breakfast excellent with really great staff notably Ali and Mohammed and Emma, aka Da Queen! Really easy access to Metro and onwards to City Centre. Front desk very helpful.Ricardo Delgado sorted out a late check out ..."

Reviewed on Jul. 30, 2025

Hilton Chicago O'Hare Airport
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 $210 per night from Aug 28 to Aug 29
CA $210
CA $246 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very Good! (1,111 reviews)
"I had a bad experience at another hotel while visiting Chicago for a basketball tournament and thankfully was able to find another hotel quickly. Upon checking in, staff member Jared was great. He was sympathetic to what I went through at the other hotel and unexpectedly gave us an upgraded junior ..."

Reviewed on Aug. 2, 2025

Marriott Chicago O'Hare
See all 2,615 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
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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 $1,010 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.