
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.




Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,915
per person
Sep 14 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.
Reviewed on Aug 8, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,173
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
My hubby & I went for a 6 day vacay in Chicago.
We stayed on the 15th floor. No view accept for the building across from us. The room accommodations were nice. Only thing missing was a ice bucket / ice, We were told we had to go to the bar to get ice. The hubby did that and they handed it to him in a plastic bag , which you know melted rather quickly. The 27 th floor Roof Top Restaurant was great. Beautiful view . Love the see through floor and the food was tasty . The daily breakfast was also filling and tasty , just wish they had an omelette station.
Great location. Centrally located where you can walk a few feet to Magificant Mile . A brisk 15 min walk will get you to Navy Pier and a 15-20 minute walk to the Riverwalk. Parking is very expensive . Overall we loved the location & accommodations .
Reviewed on Aug 8, 2026
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View all trips5* Fishing holidays in Central Chicago
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The Langham, Chicago
Downtown Chicago
CA $2,620
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
This Hotel was amazing and within walking distance from everything. The farthest we had to walk was a mile but it didnt even fill like a mile with all the things to do and see. This is the only hotel that I have ever stayed in that cleans room twice a day. You will not be disappointed, very pricey but very worth it.
Reviewed on Aug 6, 2026

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View all trips3 Night Fishing holidays in Central Chicago
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View all trips4 Night Fishing holidays in Central Chicago
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Hotel Felix River North/Magnificent Mile
Downtown Chicago
CA $907
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
I usually stay here frequently with my husband or family members when in town. I was a little disappointed with the service somewhat this last visit. This is one of my favorite areas to stay . First off l never travel without at least one other person. I noticed my booking Expedia only listed me as a guest. I reached out to the hotel via Expedia email to advise hotel that it's two guest instead of just me. I got a response back. It was fine since the room I booked would accommodate two. The first thing that was somewhat annoying to me is when I was checking in, an elderly gentleman interrupted check-in process to talk to the clerk because she spoke his language. There was no attempt by her or him to say excuse me or pardon me please. I was just standing there after getting in town and being on the road for hours to kind of be pushed aside to wait with no apology before or after. The other clerk who spoke English had just finished with a customer and I was almost tempted to jump over to the other line since she was free but my credit card and ID was in the hands of the first clerk. It was an awkward moment which I feel could have been handled better and more professionally. The icing on the cake is we were given room keys for two but I was only given enough VIP tickets for the drinks for myself. I didn't complain because maybe it was my mistake when I booked my night confirming for two instead of 1 guest. However, after dealing with being slighted by a customer interrupt
Reviewed on Aug 8, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,411
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
My hubby & I went for a 6 day vacay in Chicago.
We stayed on the 15th floor. No view accept for the building across from us. The room accommodations were nice. Only thing missing was a ice bucket / ice, We were told we had to go to the bar to get ice. The hubby did that and they handed it to him in a plastic bag , which you know melted rather quickly. The 27 th floor Roof Top Restaurant was great. Beautiful view . Love the see through floor and the food was tasty . The daily breakfast was also filling and tasty , just wish they had an omelette station.
Great location. Centrally located where you can walk a few feet to Magificant Mile . A brisk 15 min walk will get you to Navy Pier and a 15-20 minute walk to the Riverwalk. Parking is very expensive . Overall we loved the location & accommodations .
Reviewed on Aug 8, 2026

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See all available trips from Columbus to Central Chicago
View all tripsThings to do

Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend

Chicago By Night River and Lake Cruise
CA $70
per adult
92% of travellers recommend
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