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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,439, price is now CA $990 per person
CA $990
per person
Jun 25 - Jun 30
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very Good! (2,628 reviews)
The hotel was in great location downtown. The rooms and bedding was also clean and nice. We had to request a room change because the toilet and sink were not working correctly. In the new room, the bathroom sink continued to not drain. It was definitely annoying and disgusting. I probably won’t be staying here again due to the bathroom issue, but overall if that won’t bother you - it’s a good clean hotel with great staff.
Reviewed on Apr 22, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,961, price is now CA $1,233 per person
CA $1,233
per person
Jun 25 - Jun 30
found 15 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (449 reviews)
Everything was amazing from the staff to the amenities, the view and the cleanliness! I will definitely be booking again!
Reviewed on Apr 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,579, price is now CA $1,060 per person
CA $1,060
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,463 reviews)
No restaurant or available food after 10pm.
Reviewed on Apr 21, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,645, price is now CA $1,131 per person
CA $1,131
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,417 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,208, price is now CA $1,519 per person
CA $1,519
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
It’s a bit loud on the weekend. There is no daily housekeeping but great space and great location.
Reviewed on Apr 17, 2026
Wheeling Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Apr 26 to Apr 27
CA $196
CA $223 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (2,511 reviews)
Charged 2 times, once through Expedia and then again through “Hyatt”. Watch charges closely if booking through Expedia. Hyatt itself is lovely!
Reviewed on Apr 22, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $340 per night from May 9 to May 10
CA $340
CA $400 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (2,281 reviews)
Convenient but very dated. Needs a renovation. And not cheap.
Reviewed on Apr 21, 2026
Comfort Suites Chicago O'Hare Airport
4200 North River Road Schiller Park IL
Fully refundable
The price is CA $129 per night from Apr 26 to Apr 27
CA $129
CA $148 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (2,976 reviews)
Solo female traveler, stayed one night. Convenient location for early flight from O’Hare. Staff was great, room was good. Stayed on 7th floor and it smelled like a mildew cigarette in the hallways
Reviewed on Apr 22, 2026
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.
Discover the most popular places to visit in Wheeling
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Wheeling
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
