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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥387,655
per person
Nov 15 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
What an amazing hotel it is!! I just loved it. Might go again to Chicago and stay at RIU plaza❤️

Reviewed on Aug 25, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
¥490,112
per person
Oct 7 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,335 reviews)
Arlo Chicago

Arlo Chicago

Downtown Chicago
¥479,724
per person
Oct 7 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,234 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥425,614
per person
Nov 15 - Nov 20
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

Downtown Chicago
¥518,716
per person
Oct 7 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,609 reviews)
The room was just okay. It was advertised (and priced) as luxury but I would not consider this a luxury hotel. It was just an average room. The location was great. We could walk mostly everywhere. The room, beds and shower were really small. I could barely move around in the shower at all. The furniture was a little dated and had several scuff marks. I also wish there was a microwave. All in all, the hotel was fine for what we needed it for and the staff was friendly. But I would not stay here again. It was very expensive for what we got. Not really sure why this is considered a luxury hotel. That’s what happens when you mainly watch reviews from influencers who are paid to stay at the hotel.

Reviewed on Aug 25, 2026

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5* Golf vacations in Historic Route 66

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥489,023
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥663,152
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!! So many details! My husband and I were so happy!!

Reviewed on Aug 25, 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
¥975,278
per person
Oct 7 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
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3 Night Golf vacations in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥272,598
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
The views are nice. The room is more simple. The bathroom needs to be upgraded. Definitely just 3.5-4*. The late night snack area is a nice feature though.

Reviewed on Aug 25, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥336,636
per person
Nov 2 - Nov 5
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Arlo Chicago

Arlo Chicago

Downtown Chicago
¥275,762
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,234 reviews)
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4 Night Golf vacations in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥292,488
per person
Nov 2 - Nov 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
What an amazing hotel it is!! I just loved it. Might go again to Chicago and stay at RIU plaza❤️

Reviewed on Aug 25, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,064
per person
Nov 2 - Nov 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥304,077
per person
Nov 2 - Nov 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
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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.