
Central Chicago Fishing Vacations
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Flight and Fishing hotel deals in Central Chicago
Price found within the past 48 hours. Click for updated prices.



Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,344
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go.
There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable.
We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles.
Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult.
The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.
Reviewed on Sep 28, 2026


Level Chicago – Old Town
Downtown Chicago
CA $1,255
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
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Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,565
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
beautiful property in a great location highly recommend staying here this will be our go to spot when visiting chicago
Reviewed on Sep 28, 2026


The Ritz-Carlton, Chicago
Downtown Chicago
CA $1,814
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.
Reviewed on Sep 24, 2026
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Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,344
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go.
There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable.
We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles.
Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult.
The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.
Reviewed on Sep 28, 2026

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View all trips4 Night Fishing holidays in Central Chicago
Price found within the past 48 hours. Click for updated prices.


Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,077
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go.
There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable.
We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles.
Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult.
The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.
Reviewed on Sep 28, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,889
per person
Dec 23 - Dec 27
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
beautiful property in a great location highly recommend staying here this will be our go to spot when visiting chicago
Reviewed on Sep 28, 2026
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Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
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