
Wheeling Vacations from ¥206,246
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The Latest Wheeling Vacation Packages
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,609 reviews)
Beautiful spacious well thought room with no dust, beautiful views of the lake and river and buildings, perfect staff teams (front desk, bellboys, housekeeper team)! I will be back at the same room!
Reviewed on Jun 19, 2025

The Peninsula Chicago
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The customer service was top notch, everyone went above and beyond to make my stay an exceptional experience!! 5 Stars All around!!
Reviewed on Jun 10, 2025


Level Chicago – Old Town
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!
Reviewed on Jun 1, 2025
Find the Best Wheeling Vacation Packages
Wheeling Hotel Deals

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is ¥19,575 per night from Jul 4 to Jul 5
¥19,575
¥22,311 total
Jul 4 - Jul 5
includes taxes & fees
8.6/10 Excellent! (1,636 reviews)
"Great!"
Reviewed on Jun 17, 2025

Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥25,991 per night from Jul 12 to Jul 13
¥25,991
¥30,508 total
Jul 12 - Jul 13
includes taxes & fees
8/10 Very Good! (2,063 reviews)
"It was nice to be so close to the airport for our early morning flight."
Reviewed on Jun 17, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd, Rosemont, IL
Fully refundable
The price is ¥16,204 per night from Jun 30 to Jul 1
¥16,204
¥18,469 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (2,211 reviews)
"Very convenient location. Close tonthe fashion outlets and to the airport"
Reviewed on Jun 18, 2025
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.
Frequently asked questions
Discover the most popular places to visit in Wheeling

Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Michigan Avenue
4.5/5(332 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.
What to do in Wheeling

Wendella's 90-min Chicago River Architecture Tour
¥6,507
per adult
94% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
¥3,499
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.