
Southern Wisconsin Pet-friendly Vacations
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Top Pet-friendly vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Freehand Chicago
Downtown Chicago
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Price was NT$36,489, price is now NT$24,884 per person
NT$24,884
per person
Sep 2 - Sep 6
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
7.8/10 Good! (3,204 reviews)
I would not stay at the Freehand again. Our stay was a mess from the moment we checked in. They said we had “checked in” already, but we had not yet been to the property yet. They had to give us a new room.
When we got to our room, the room was not very clean. There was still trash from the last guests. When we left the sign for them to clean our room, all they did was give us new towels.
The bed is also shorter than most queens; I’m tall and I could not fully extend my legs. The walls are also paper thin, and other guests were screaming down the hall until 1 a.m. It was not easy to get a good night’s rest here.
The building has also not been updated. An old building can have charm, but this one did not. The doors were nearly impossible to open—this was for all doors in our hall. I heard other guests struggling with their doors too. The AC does not work very well. I had it set to 60 and was sweating most of the night. There was a persistent musty smell throughout our stay.
I did feel safe at this property, but then again, Chicago is relatively safe. The showers had consistent water pressure and warmth. The location was also convenient. Other than these few things, I was disappointed with the quality of the hotel.
I generally don’t expect much out of a hotel. I need a safe and clean place to lay my head at night, and this didn’t quite clear my bar for those things.
Reviewed on 2026/8/1


Level Chicago - River North
Downtown Chicago
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Price was NT$42,185, price is now NT$26,174 per person
NT$26,174
per person
Sep 9 - Sep 13
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities
Reviewed on 2026/7/30

Hotel Felix River North/Magnificent Mile
Downtown Chicago
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Price was NT$41,585, price is now NT$26,217 per person
NT$26,217
per person
Sep 2 - Sep 6
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,858 reviews)
fabulous location and helpful staff.
Reviewed on 2026/8/1

Level Chicago Fulton Market
Downtown Chicago
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Price was NT$47,847, price is now NT$31,430 per person
NT$31,430
per person
Sep 2 - Sep 6
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Comes with all the comforts of
Home.
Reviewed on 2026/7/29
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View all trips5* Pet-friendly vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
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Price was NT$66,385, price is now NT$47,295 per person
NT$47,295
per person
Sep 2 - Sep 6
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,945 reviews)
Very excellent service
Reviewed on 2026/7/31
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View all trips4 Night Pet-friendly vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was NT$42,185, price is now NT$26,174 per person
NT$26,174
per person
Sep 9 - Sep 13
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,038 reviews)
This was the best hotel I’ve stayed in in my life. I came here for the first time to Chicago and me and my girl. Upon arrival they gave us a complementary room upgrade. Where are they doing that at so as you can see, I am very happy with our stay so I will recommend this hotel to anybody and I think we might even come back here again. You know any they have good amenities
Reviewed on 2026/7/30


Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was NT$41,585, price is now NT$26,217 per person
NT$26,217
per person
Sep 2 - Sep 6
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,858 reviews)
fabulous location and helpful staff.
Reviewed on 2026/8/1
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
