Historic Route 66 Pet-friendly Vacations

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Top Pet-friendly vacation packages in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
¥364,204
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,161 reviews)
It's a great spot to be and walking distance to all the great things in Downtown Chicago

Reviewed on Aug 17, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥405,665
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
N/a

Reviewed on Aug 18, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
¥379,826
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥429,498
per person
Oct 7 - Oct 11
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Nice neat clean room. It was a lot community so you felt safe.

Reviewed on Aug 18, 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

Downtown Chicago
¥393,084
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (4,495 reviews)
We finally found our first-choice hotel for Chicago! Our stay was great and the staff was outstanding— top-notch level of friendliness and helpfulness. We travel with a wheelchair and found the accessibility suitable as well.

Reviewed on Aug 18, 2026

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5* Pet-friendly 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
¥330,966
per person
Nov 5 - Nov 9
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥425,405
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on Aug 16, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥470,451
per person
Nov 5 - Nov 9
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
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3 Night Pet-friendly vacations in Historic Route 66

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
¥290,243
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,899 reviews)
Great location and pleasant staff.

Reviewed on Aug 17, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥364,382
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Overall, this is a great hotel. My family loved the rooms and the fitness center. The staff were mostly great too. We will definitely stay here again if we come back to Chicago. We were given rooms that were 28 floors apart despite making our reservation months in advance. Yes, it was one reservation which included 2 rooms. Both the shower and toilet space was fairly tight. Other than that, we are very happy.

Reviewed on Aug 18, 2026

L7 Chicago by LOTTE

L7 Chicago by LOTTE

Downtown Chicago
¥317,097
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (4,495 reviews)
We finally found our first-choice hotel for Chicago! Our stay was great and the staff was outstanding— top-notch level of friendliness and helpfulness. We travel with a wheelchair and found the accessibility suitable as well.

Reviewed on Aug 18, 2026

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4 Night Pet-friendly 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
¥330,966
per person
Nov 5 - Nov 9
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥429,498
per person
Oct 7 - Oct 11
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Nice neat clean room. It was a lot community so you felt safe.

Reviewed on Aug 18, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥425,405
per person
Nov 5 - Nov 9
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on Aug 16, 2026

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