Northwest Side Fishing Vacations
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Flight and Fishing hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,543, price is now CA $1,017 per person
CA $1,017
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Very quiet, really clean and staff was great
Reviewed on Apr 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,848, price is now CA $1,934 per person
CA $1,934
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,735, price is now CA $1,305 per person
CA $1,305
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Room was super clean. The view all the way down to the lake from balcony was nice.
Reviewed on Apr 2, 2026
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View all trips5* Fishing holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,555, price is now CA $2,079 per person
CA $2,079
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on Mar 31, 2026
The St. Regis Chicago
Downtown Chicago
Price was CA $2,381, price is now CA $1,949 per person
CA $1,949
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (104 reviews)
The hotel was extremely clean but the room itself reminded me of a nice condo, not a luxury hotel. Our room looked right into an apartment building with no view of the water. The restaurants, which were excellent, were highly overpriced, more so than at other nice restaurants in the city. We could not use their car service as the driver left before 8pm. The pool and gym are the highlights of the hotel. The staff were also incredibly kind and attentive. Note that valet parking is priced per night. Overall, I would not return to this location because of the room quality, but the staff deserve a huge shoutout.
Reviewed on Mar 12, 2026
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View all trips3 Night Fishing holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,543, price is now CA $1,017 per person
CA $1,017
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Very quiet, really clean and staff was great
Reviewed on Apr 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,613, price is now CA $1,020 per person
CA $1,020
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
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See all available trips from Columbus to Northwest Side
View all trips4 Night Fishing holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $2,848, price is now CA $1,934 per person
CA $1,934
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer.
Buffet breakfast is included and that makes it very good value. Hotel also has a gym/
Not too many amenities in the room though.
Reviewed on Apr 2, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,997, price is now CA $1,521 per person
CA $1,521
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Room was super clean. The view all the way down to the lake from balcony was nice.
Reviewed on Apr 2, 2026
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