Wheeling Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
DoubleTree by Hilton Chicago Schaumburg
Price was CA $878, price is now CA $589 per person
CA $589
per person
Nov 9 - Nov 15
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.4/10 Good! (1,004 reviews)
Quick stay in between traveling. The bed and bedding comfortable. Room is spacious. Staff friendly.
Reviewed on Aug. 30, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,757, price is now CA $1,066 per person
CA $1,066
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Place is great, staff, location.
So many great restaurants, river boats, shopping.
Loved our stay at Trump International
Reviewed on Aug. 31, 2025
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,831, price is now CA $1,198 per person
CA $1,198
per person
Oct 25 - Oct 29
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.
Reviewed on Aug. 24, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $1,922, price is now CA $1,279 per person
CA $1,279
per person
Oct 22 - Oct 25
found 9 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $974, price is now CA $654 per person
CA $654
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The staff were so welcoming! They knew it was our anniversary and we got showered with little nice surprises. Thank you so much for making our stay so memorable and meaningful. Our room was perfect, the lobby and the bar/lounge were beautiful and again the staff were great. Location is within 15 minute walk to every thing. We will definitely be back!
Reviewed on Aug. 31, 2025
Wheeling Hotel Deals
Marriott Chicago O'Hare
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Sep 19 to Sep 20
CA $209
CA $245 total
Sep 19 - Sep 20
includes taxes & fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 19 to Sep 20
CA $197
CA $224 total
Sep 19 - Sep 20
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Sep 26 to Sep 27
CA $246
CA $289 total
Sep 26 - Sep 27
includes taxes & fees
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
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(19 reviews)
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.
Navy Pier
4.5/5(459 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Wheeling
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
CA $62
per adult
96% of travellers recommend
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.