Winnebago Vacation Packages
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Top Winnebago Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,443, price is now CA $1,038 per person
CA $1,038
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,155, price is now CA $1,480 per person
CA $1,480
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,384, price is now CA $1,717 per person
CA $1,717
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
The hotel is in the best location in the city. The staff is very friendly and rooms are immaculate. Terrace 16 restaurant and bar in the hotel has a great view. Overall experience was wonderful highly recommend and will definitely be back soon.
Reviewed on May 11, 2026
Winnebago Hotel Deals
Baymont by Wyndham Rockford
662 N Lyford Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from May 25 to May 26
CA $106
CA $120 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,636 reviews)
Quick overnight in a dog friendly property. Convenient location and good for our needs.
Reviewed on May 11, 2026
Riverview Inn & Suites, an Ascend Collection Hotel
700 W Riverside Blvd Rockford IL
Fully refundable
The price is CA $140 per night from May 25 to May 26
CA $140
CA $159 total
May 25 - May 26
includes taxes & fees
8.4/10 Very Good! (1,021 reviews)
The hotel was under construction in some areas, but this did not affect our stay in any way. The staff was pleasant and very helpful. The room was comfortable. There is a restaurant on site that opens at 5pm. There is little information online about it, but it is not a high end restaurant as depicted. ...
Reviewed on May 11, 2026
Extended Stay America Suites Rockford I90
653 Clark Rd Rockford IL
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from May 13 to May 14
CA $98
CA $112 total
May 13 - May 14
includes taxes & fees
7.6/10 Good! (955 reviews)
Clean room
Reviewed on May 10, 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.
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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.
