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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,293, price is now CA $1,451 per person
CA $1,451
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The staff was very kind and check in/out was quick. Great breakfast buffet!

Reviewed on Mar 24, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,347, price is now CA $1,510 per person
CA $1,510
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Rooms are nice, great view, valet parking is great

Reviewed on Mar 24, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was CA $2,104, price is now CA $1,573 per person
CA $1,573
per person
Jun 3 - Jun 8
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
The entire hotel was a 10/10. Would definitely recommend. Also the bartender KERRY in the restaurant of the hotel was perfect, very nice, personable, and made our stay even better!!!

Reviewed on Mar 23, 2026

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Price was CA $1,970, price is now CA $1,474 per person
CA $1,474
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans! The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too! The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well! All and all it’s a wonderful place to experience!!!!🍍

Reviewed on Mar 18, 2026

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Wheeling Hotel Deals

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 $314 per night from Apr 24 to Apr 25
CA $314
CA $368 total
Apr 24 - Apr 25
includes taxes & fees
8.4/10 Very Good! (2,235 reviews)
N/A

Reviewed on Mar 24, 2026

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 $185 per night from Apr 6 to Apr 7
CA $185
CA $211 total
Apr 6 - Apr 7
includes taxes & fees
8.8/10 Excellent! (2,431 reviews)
Architecturally beautiful hotel. Our room was very clean, updated, crisp linens, good bed and pillows. We paid for the breakfast buffet and it was well worth it. I really enjoyed my stay at this Hyatt. It will be my go to whenever I need to stay near O'hare.

Reviewed on Mar 24, 2026

Hyatt Regency O'Hare Chicago
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 $204 per night from Apr 3 to Apr 4
CA $204
CA $240 total
Apr 3 - Apr 4
includes taxes & fees
8.6/10 Excellent! (1,237 reviews)
It was all good!

Reviewed on Mar 23, 2026

Marriott Chicago O'Hare
See all 2,754 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

4.5/5(159 reviews)

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

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(20 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.

Michigan Avenue
Chicago Skyline at North Beach

Naval Base Great Lakes

4.5/5(3 reviews)

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.

Naval Base Great Lakes

What to do in Wheeling

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $36
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Wheeling

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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.