Southern Wisconsin Adults Only Vacations
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Flight and Adults Only hotel deals in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Price was CA $1,406, price is now CA $853 per person
CA $853
per person
Apr 23 - Apr 28
found 22 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,969, price is now CA $1,108 per person
CA $1,108
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!
Reviewed on Feb 27, 2026
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $2,238, price is now CA $1,618 per person
CA $1,618
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.
Reviewed on Feb 26, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $1,857, price is now CA $1,381 per person
CA $1,381
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at
Reviewed on Feb 26, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,167, price is now CA $884 per person
CA $884
per person
Apr 16 - Apr 19
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .
Reviewed on Feb 17, 2026
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,484, price is now CA $1,147 per person
CA $1,147
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
We had a great stay!
Reviewed on Feb 23, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $1,857, price is now CA $1,381 per person
CA $1,381
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at
Reviewed on Feb 26, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,136, price is now CA $1,638 per person
CA $1,638
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!
Reviewed on Feb 20, 2026
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Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,167, price is now CA $884 per person
CA $884
per person
Apr 16 - Apr 19
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again .
Reviewed on Feb 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,969, price is now CA $1,108 per person
CA $1,108
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!
Reviewed on Feb 27, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $1,857, price is now CA $1,381 per person
CA $1,381
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was amazing. Staff was fantastic. Best Hotel we have ever stayed at
Reviewed on Feb 26, 2026
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View all trips4 Night Adults Only holidays in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
La Banque Hotel
Price was CA $1,068, price is now CA $767 per person
CA $767
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,261, price is now CA $965 per person
CA $965
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.
Reviewed on Feb 26, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $2,136, price is now CA $1,638 per person
CA $1,638
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!
Reviewed on Feb 20, 2026
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