
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.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,834, price is now CA $1,264 per person
CA $1,264
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This hotel is a steal- wasn’t sure what to expect bc the price was such a good deal but we Loved it. Amazing location, great restaurant on site, our whole family all slept well in the room. 2 beds plus a pullout. Such comfortable and luxury bedding too.
Would def come back and highly recommend. Staff was super friendly and kind too!
Reviewed on Jul 10, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $2,287, price is now CA $1,612 per person
CA $1,612
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,587, price is now CA $1,153 per person
CA $1,153
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
The hotel and staff were great, the location even better. Comfortable and well equipped suite.
Reviewed on Jul 10, 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 $2,000, price is now CA $1,528 per person
CA $1,528
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
Excellent service. Room was fantastic with an incredible view of the city. Definitely worth every penny! Will go back for sure!
Reviewed on Jul 9, 2026

The Peninsula Chicago
Downtown Chicago
Price was CA $3,702, price is now CA $3,201 per person
CA $3,201
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
The most helpful staff. The most comfortable bed. The most luxurious bathroom. The Peninsula is unrivaled amongst the five-star hotels. Cannot wait to return yet again!
Reviewed on Jul 5, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was CA $1,905, price is now CA $1,659 per person
CA $1,659
per person
Sep 11 - Sep 14
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026
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See all available trips from Columbus to Northwest Side
View all trips3 Night Fishing holidays in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,834, price is now CA $1,264 per person
CA $1,264
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This hotel is a steal- wasn’t sure what to expect bc the price was such a good deal but we Loved it. Amazing location, great restaurant on site, our whole family all slept well in the room. 2 beds plus a pullout. Such comfortable and luxury bedding too.
Would def come back and highly recommend. Staff was super friendly and kind too!
Reviewed on Jul 10, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026
Don't see what you're looking for?
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 Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,737, price is now CA $1,169 per person
CA $1,169
per person
Sep 11 - Sep 15
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.
Reviewed on Jul 9, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,824, price is now CA $1,274 per person
CA $1,274
per person
Sep 11 - Sep 15
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.
Reviewed on Jul 8, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $2,582, price is now CA $1,834 per person
CA $1,834
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all tripsThings to do

Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend

Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
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