
West Side Kid friendly Vacations
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Top Kid friendly vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.



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


5* Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.


Four Seasons Hotel Chicago
Downtown Chicago
¥425,405
per person
Nov 5 - Nov 9
found 3 hours 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

3 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.


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
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
4 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.



Four Seasons Hotel Chicago
Downtown Chicago
¥425,405
per person
Nov 5 - Nov 9
found 3 hours 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
Things to do

Chicago: Navy Pier Centennial Wheel Ticket
¥3,920
per adult
90% of travellers recommend

Chicago: Willis Tower Skydeck and The Ledge Ticket
¥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

