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Anola Vacation Packages

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Anola Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Canad Inns Destination Centre Windsor Park

Canad Inns Destination Centre Windsor Park

3 out of 5
Price was $791, price is now $721 per person
$721
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this family-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.

Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Price was $883, price is now $776 per person
$776
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.

Inn At The Forks

Inn At The Forks

3.5 out of 5
Price was $1,086, price is now $961 per person
$961
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this spa hotel in Winnipeg. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Great

Reviewed on Oct 13, 2026

Hyatt House Winnipeg-South/Outlet Collection

Hyatt House Winnipeg-South/Outlet Collection

3 out of 5
Price was $1,081, price is now $982 per person
$982
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Outlet Collection Winnipeg and Polo Park are located nearby.
I will stay here again.

Reviewed on Oct 13, 2026

Canad Inns Destination Centre Transcona

Canad Inns Destination Centre Transcona

3 out of 5
Price was $805, price is now $738 per person
$738
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this family-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Canada Life Centre and Transcona Golf Club are located nearby.

Norwood Hotel

Norwood Hotel

3 out of 5
Price was $891, price is now $819 per person
$819
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Large clean room, comfortable king bed! Easy check in - check out. Restaurant downstairs was great!

Reviewed on Oct 13, 2026

Canad Inns Destination Centre Club Regent Casino Hotel

Canad Inns Destination Centre Club Regent Casino Hotel

3 out of 5
Price was $833, price is now $773 per person
$773
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this business-friendly hotel in Winnipeg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Canada Life Centre and Club Regent Casino are located nearby.

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel

4 out of 5
Price was $886, price is now $826 per person
$826
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Book a stay at this spa hotel in Winnipeg. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Canada Life Centre and Polo Park are located nearby.
Our experience at the Garry Hotel was exceptional. Breakfast was delicious (best avocado toast) I've ever had) The front desk personnel were helpful and courteous. The TEN spa was expensive but delightful. I had a facial that included dermabrasion and oxygen treatment. You can use their other facilities as well: steam room, eucalyptus mist shower, tea and coffee service with incredible bakery goods.

Reviewed on Oct 14, 2026

Anola Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Canad Inns Destination Centre Windsor Park

Canad Inns Destination Centre Windsor Park

3 out of 5
Windsor Park
Price was $791, price is now $721 per person
$721
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Humphry Inn & Suites

Humphry Inn & Suites

2.5 out of 5
Downtown Winnipeg
Price was $883, price is now $776 per person
$776
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Inn At The Forks

Inn At The Forks

3.5 out of 5
Downtown Winnipeg
Price was $1,086, price is now $961 per person
$961
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)
Hyatt House Winnipeg-South/Outlet Collection

Hyatt House Winnipeg-South/Outlet Collection

3 out of 5
Price was $1,081, price is now $982 per person
$982
per person
Dec 1 - Dec 4
found 24 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Winnipeg (YWG)

Anola Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Winnipeg Downtown by IHG

Holiday Inn & Suites Winnipeg Downtown by IHG

3 out of 5
Downtown Winnipeg
Price was $902, price is now $896 per person
$896
per person
Dec 4 - Dec 9
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)
Alt Hotel Winnipeg

Alt Hotel Winnipeg

3 out of 5
Downtown Winnipeg
Price was $927, price is now $923 per person
$923
per person
Dec 4 - Dec 9
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Winnipeg (YWG)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Flair Airlines
Sat, Nov 28 - Fri, Dec 11
YVR
Vancouver Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Sat, Nov 28 from Vancouver Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Dec 11, priced at $219 found 1 day ago
Flair Airlines
Wed, Oct 28 - Fri, Oct 30
YYZ
Pearson Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$241 Roundtrip, found 19 hours ago
$241
Roundtrip
found 19 hours ago
Select Flair Airlines flight, departing Wed, Oct 28 from Pearson Intl. to Winnipeg James Armstrong Richardson Intl., returning Fri, Oct 30, priced at $241 found 19 hours ago
WestJet
Thu, Dec 17 - Thu, Dec 17
YYC
Calgary Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$282 Roundtrip, found 12 hours ago
$282
Roundtrip
found 12 hours ago
Select WestJet flight, departing Thu, Dec 17 from Calgary Intl. to Winnipeg James Armstrong Richardson Intl., returning Thu, Dec 17, priced at $282 found 12 hours ago
WestJet
Fri, Oct 30 - Sat, Oct 31
YEG
Edmonton Intl.
YWG
Winnipeg James Armstrong Richardson Intl.
$333 Roundtrip, found 3 days ago
$333
Roundtrip
found 3 days ago
Select WestJet flight, departing Fri, Oct 30 from Edmonton Intl. to Winnipeg James Armstrong Richardson Intl., returning Sat, Oct 31, priced at $333 found 3 days ago