Historic Route 66 Fishing Vacations
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Flight and Fishing hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,594, price is now CA $1,111 per person
CA $1,111
per person
Jun 18 - Jun 21
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $3,272, price is now CA $2,122 per person
CA $2,122
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago
Reviewed on Apr 10, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,775, price is now CA $1,201 per person
CA $1,201
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,647, price is now CA $1,868 per person
CA $1,868
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.
Reviewed on Apr 11, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,861, price is now CA $1,346 per person
CA $1,346
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
I booked this stay specifically because I saw they had a steam room and Sauna. They were both very pleasant and available 24/7. The room was very high quality with great views but if the city. The game rooms looked really nice and spacious but I sadly didn’t have time to enjoy that aspect of the hotel. There is also a great cafe and bakery connected to the lobby. I’m excited to book here again with a little more time to make the most of my stay
Reviewed on Apr 11, 2026
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View all trips5* Fishing holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,125, price is now CA $1,622 per person
CA $1,622
per person
Jun 18 - Jun 21
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $3,202, price is now CA $2,322 per person
CA $2,322
per person
May 31 - Jun 3
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Top of the line customer service! I can’t express how deeply I am impressed with your hotel, the feel, the specialness of it all! My first time there, has left me with a lasting impression I will never forget! Classy and it smelled like Paris! Love everything about the hotel. Wish I could have stayed longer. Thank you for keeping such a prestigious hotel at top standard!
Reviewed on Apr 6, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $2,847, price is now CA $2,069 per person
CA $2,069
per person
May 31 - Jun 3
found 9 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
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View all trips3 Night Fishing holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,594, price is now CA $1,111 per person
CA $1,111
per person
Jun 18 - Jun 21
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!
Reviewed on Apr 3, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,863, price is now CA $1,907 per person
CA $1,907
per person
May 29 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.
Reviewed on Apr 11, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,775, price is now CA $1,201 per person
CA $1,201
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
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See all available trips from Columbus to Historic Route 66
View all trips4 Night Fishing holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,735, price is now CA $1,101 per person
CA $1,101
per person
Jun 18 - Jun 22
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago
Reviewed on Apr 10, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,143, price is now CA $1,392 per person
CA $1,392
per person
Jun 18 - Jun 22
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
We love staying at the Sable. Easy in and out parking. The Valet staff is wonderful. We enjoyed our breakfast. The room and view is always amazing.
Reviewed on Apr 11, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,806, price is now CA $1,234 per person
CA $1,234
per person
Jun 18 - Jun 22
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool!
The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran
Reviewed on Apr 7, 2026
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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.
