Northwest Chicago Fishing Vacations

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Flight and Fishing hotel deals in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,063
per person
Nov 19 - Nov 22
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Close to every things, great location

Reviewed on Oct 16, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
CA $1,152
per person
Jan 3 - Jan 9
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.6/10 Excellent! (1,015 reviews)
Good property but a very small bathroom and no ho water.

Reviewed on Oct 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,122
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
El edificio es muy bueno, la atención del personal pésimo, siempre mal predispuestos para ayudar!

Reviewed on Oct 17, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,163
per person
Dec 28 - Jan 1
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
An honest reflection over the Chicago Marathon weekend -in which we were running. The hotel itself is in an excellent location for downtown, the lake (and the marathon.) the views are stunning and the room was clean and comfortable. BUT - there was no consideration for guests who were running. No early breakfast (unlike in Boston) no washrooms or showers for guests to use after the marathon. checkout was 11am - therefore we had to checkout at 5am because of the race. No understanding of the need to wash, change for a long transatlantic flight back that evening (Unlike Boston); no understanding of my wife's immune-suppressed condition - even after the marathon. A refusal to help with any form of hygiene in terms of getting washed, showered and changed. (In a hotel with over 700 rooms) Other running participants - were complaining too. I accept it was our decision to leave the same day a the race, but the blanket lack of help amongst the staff was staggering and I would argue lacked basic human decency. (We got changed in a toilet before heading to the airport.)

Reviewed on Oct 17, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
CA $1,437
per person
Jan 3 - Jan 9
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
Clean room, great staff

Reviewed on Oct 17, 2026

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5* Fishing holidays in Northwest Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,437
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
CA $2,091
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
Save 100% on your flight
CA $1,725
per person
Nov 17 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
Excellent experience. I’d recommend this property for their outstanding service and updated rooms.

Reviewed on Oct 9, 2026

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3 Night Fishing holidays in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
CA $668
per person
Nov 23 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.6/10 Excellent! (1,015 reviews)
Good property but a very small bathroom and no ho water.

Reviewed on Oct 17, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,063
per person
Nov 19 - Nov 22
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Close to every things, great location

Reviewed on Oct 16, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,280
per person
Nov 19 - Nov 22
found 24 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
Don't see what you're looking for?
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4 Night Fishing holidays in Northwest 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 $928
per person
Nov 18 - Nov 22
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,194
per person
Nov 18 - Nov 22
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Close to every things, great location

Reviewed on Oct 16, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,163
per person
Dec 28 - Jan 1
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
An honest reflection over the Chicago Marathon weekend -in which we were running. The hotel itself is in an excellent location for downtown, the lake (and the marathon.) the views are stunning and the room was clean and comfortable. BUT - there was no consideration for guests who were running. No early breakfast (unlike in Boston) no washrooms or showers for guests to use after the marathon. checkout was 11am - therefore we had to checkout at 5am because of the race. No understanding of the need to wash, change for a long transatlantic flight back that evening (Unlike Boston); no understanding of my wife's immune-suppressed condition - even after the marathon. A refusal to help with any form of hygiene in terms of getting washed, showered and changed. (In a hotel with over 700 rooms) Other running participants - were complaining too. I accept it was our decision to leave the same day a the race, but the blanket lack of help amongst the staff was staggering and I would argue lacked basic human decency. (We got changed in a toilet before heading to the airport.)

Reviewed on Oct 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Northwest Chicago
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Northwest 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.