Historic Route 66 Fishing Vacations
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Top Fishing vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was ￥358,742, price is now ￥285,163 per person
￥285,163
per person
Jun 26 - Jun 30
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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 ￥661,897, price is now ￥521,872 per person
￥521,872
per person
Jun 1 - Jun 8
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) 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
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥395,459, price is now ￥331,965 per person
￥331,965
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The breakfast was delicious. A great stay in downtown Chicago.
Reviewed on Apr 12, 2026
Sentral Michigan Avenue
Downtown Chicago
Price was ￥366,849, price is now ￥315,772 per person
￥315,772
per person
Jun 26 - Jun 30
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,117 reviews)
Great hotel for the price! Fun game room and pool for the kids. Walking distance from the Aquarium, Museum, planetarium, and Willis Tower.
Reviewed on Apr 7, 2026
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View all trips5* Fishing vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥416,357, price is now ￥360,758 per person
￥360,758
per person
Jun 13 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥463,540, price is now ￥410,870 per person
￥410,870
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Beautiful and in walking distance to so many shops and cafes! We had a great stay.
Reviewed on Apr 6, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥527,010, price is now ￥469,872 per person
￥469,872
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) 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 vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥395,459, price is now ￥331,965 per person
￥331,965
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The breakfast was delicious. A great stay in downtown Chicago.
Reviewed on Apr 12, 2026
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥387,721, price is now ￥334,418 per person
￥334,418
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (2,471 reviews)
Staff was friendly, however I asked to have blankets brought up to room two times (one phone call and one text) and there was no follow through. The room smelled like stale smoke. The pull out bed was awful and you could feels the bedsprings. They also offered to bring coffee to the room and when I requested a time, it was never delivered. I mentioned to from desk and they apologized and had coffee sent to room, however we were ready to check out. They did offer a late check out and staff was friendly. We were dissapointed that we couldn't pay cash, although that wouldn't have been a deal breaker. Rooms could use a little updating.
Reviewed on Apr 4, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥397,724, price is now ￥347,208 per person
￥347,208
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Nice, but no microwave or refrigerator in room. Staff is nice and place was clean. Many things to do around.
Reviewed on Apr 11, 2026
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See all available trips from Osaka to Historic Route 66
View all trips4 Night Fishing vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥365,491, price is now ￥275,432 per person
￥275,432
per person
Jun 26 - Jun 30
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The breakfast was delicious. A great stay in downtown Chicago.
Reviewed on Apr 12, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥479,394, price is now ￥368,196 per person
￥368,196
per person
Jun 26 - Jun 30
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!
Reviewed on Apr 7, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥358,742, price is now ￥285,163 per person
￥285,163
per person
Jun 26 - Jun 30
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
