Far Southeast Side Fishing Vacations
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Flight and Fishing hotel deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip
Price was CA $1,188, price is now CA $880 per person
CA $880
per person
Apr 9 - Apr 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
Everything was perfect and the front desk was so nice
Reviewed on Feb 10, 2026
Stay One Chicago
Downtown Chicago
Price was CA $3,061, price is now CA $2,385 per person
CA $2,385
per person
Apr 28 - May 4
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel".
So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into.
Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I).
The app never worked, and we finally got physical key cards from the guy working for the building.
There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced.
I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.
Reviewed on Feb 10, 2026
Hyatt Regency Chicago
Downtown Chicago
Price was CA $926, price is now CA $723 per person
CA $723
per person
Apr 3 - Apr 6
just found
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,386 reviews)
Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned
Reviewed on Feb 10, 2026
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View all trips5* Fishing holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $1,792, price is now CA $1,452 per person
CA $1,452
per person
Apr 3 - Apr 6
just found
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,206, price is now CA $2,509 per person
CA $2,509
per person
Apr 28 - May 4
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Everything was great… but the staff was absolutely amazing!
Thank you for taking such great care of us.
Reviewed on Jan 24, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,912, price is now CA $1,536 per person
CA $1,536
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
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View all trips3 Night Fishing holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,598, price is now CA $1,215 per person
CA $1,215
per person
Mar 17 - Mar 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
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View all trips4 Night Fishing holidays in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was CA $1,183, price is now CA $876 per person
CA $876
per person
Apr 29 - May 3
found 4 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Staff was excellent and the building is literally iconic. Our only negative is that the bathrooms were a bit tired. Ours had a yellowed, loose fitting toilet seat and a light out on the mirror.
Reviewed on Feb 2, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,409, price is now CA $1,720 per person
CA $1,720
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
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