
Historic Route 66 Golf Vacations
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Top Golf vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ¥419,910, price is now ¥349,994 per person
¥349,994
per person
May 29 - Jun 1
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,326 reviews)
Room was nice and clean, decent view.
Perfect location. Close to shopping and nice restaurants.
Staff was amazing; Myron in particular was so kind and accommodating.
Reviewed on Mar 8, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥659,915, price is now ¥426,058 per person
¥426,058
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Increíble hotel y desayuno
Reviewed on Mar 12, 2026

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was ¥560,889, price is now ¥424,265 per person
¥424,265
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥505,796, price is now ¥391,960 per person
¥391,960
per person
May 28 - Jun 1
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on Mar 13, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥415,929, price is now ¥356,362 per person
¥356,362
per person
May 29 - Jun 1
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,613 reviews)
Nearby Magnificent Mile.
Reviewed on Mar 12, 2026
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View all trips5* Golf vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Four Seasons Hotel St Louis
Downtown St. Louis
Price was ¥356,932, price is now ¥346,216 per person
¥346,216
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Tokyo (HND) to St. Louis (STL)
9.4/10 Exceptional! (1,001 reviews)
Beautiful accommodations. Attentive and genuine staff. We felt like celebrities. Beyond first class service!!
Reviewed on Feb 23, 2026


The Ritz-Carlton, St. Louis
Clayton
Price was ¥574,842, price is now ¥567,143 per person
¥567,143
per person
May 1 - May 5
found 19 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to St. Louis (STL)
9.2/10 Wonderful! (557 reviews)
Excellent hotel with various restaurants and expansive lobby area.. staff very attentive.
Reviewed on Feb 6, 2026
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View all trips3 Night Golf vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.


Eurostars Magnificent Mile
Downtown Chicago
Price was ¥465,726, price is now ¥372,726 per person
¥372,726
per person
May 29 - Jun 1
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on Mar 12, 2026

Level Chicago - River North
Downtown Chicago
Price was ¥452,740, price is now ¥368,338 per person
¥368,338
per person
May 29 - Jun 1
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (858 reviews)
I would stay here again without a second thought. Great
Reviewed on Mar 11, 2026
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View all trips4 Night Golf vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Price was ¥452,888, price is now ¥384,245 per person
¥384,245
per person
May 28 - Jun 1
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,201 reviews)
We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.
Reviewed on Mar 9, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥505,796, price is now ¥391,960 per person
¥391,960
per person
May 28 - Jun 1
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on Mar 13, 2026

The Wildwood Hotel
Price was ¥464,028, price is now ¥406,504 per person
¥406,504
per person
May 1 - May 5
found 19 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to St. Louis (STL)
9.2/10 Wonderful! (1,626 reviews)
Place was nice. Had handicap room. No living room type chair, just computer chair. Hot tub was like a four-seater and only two mild jets. Main pool half size of most and a nly went from 3 feet to 4 feet. Very small. Breakfast was excellent.
Reviewed on Mar 11, 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.
