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.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $786
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
CA $808
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,686
per person
Sep 14 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

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

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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5* Fishing holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,660
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Great experience!

Reviewed on Aug 7, 2026

The Langham, Chicago

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

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $2,136
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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3 Night Fishing holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,080
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $3,103
per person
Sep 15 - Sep 18
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,686
per person
Sep 14 - Sep 17
found 11 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
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4 Night Fishing holidays in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

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

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

Freehand Chicago

Freehand Chicago

Downtown Chicago
CA $1,264
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
7.8/10 Good! (3,233 reviews)
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $70
per adult
92% of travellers recommend
Chicago By Night River and Lake Cruise
See all activities in Central Chicago

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.