
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 – Old Town
Downtown Chicago
Price was ¥250,082, price is now ¥191,525 per person
¥191,525
per person
Jan 25 - Jan 30
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was ¥371,466, price is now ¥260,622 per person
¥260,622
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥402,036, price is now ¥316,946 per person
¥316,946
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18.8/10 Exceptional! (1,771 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.
Reviewed on Nov 14, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥383,892, price is now ¥316,307 per person
¥316,307
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥301,902, price is now ¥260,239 per person
¥260,239
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
17.6/10 Exceptional! (3,098 reviews)
Room was just okay not what I expected for the price. Front staff and other staff in passing were very helpful and friendly.
Reviewed on Nov 17, 2025
5* Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Park Hyatt Chicago
Downtown Chicago
Price was ¥383,892, price is now ¥316,307 per person
¥316,307
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥402,036, price is now ¥316,946 per person
¥316,946
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18.8/10 Exceptional! (1,771 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.
Reviewed on Nov 14, 2025

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

Freehand Chicago
Downtown Chicago
Price was ¥186,932, price is now ¥185,828 per person
¥185,828
per person
Dec 23 - Dec 26
found 2 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
16/10 Exceptional! (2,569 reviews)
Location-Amazing, Overall Vibe-AMAZING Service-Phenomenal but the actual room was eh at best. The size is why you pay for so no complaint about being too small, the walls were just dirty. Corner of the rooms dirty with dust. I will say the mattress was insanely comfortable.
Reviewed on Nov 17, 2025

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ¥240,592, price is now ¥224,122 per person
¥224,122
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.4/10 Exceptional! (1,261 reviews)
Staff were exceptional, check-in was easy, the room was beautiful, and the overall experience was excellent.
Reviewed on Nov 16, 2025

Comfort Suites Lombard - Addison
Price was ¥196,866, price is now ¥194,026 per person
¥194,026
per person
Dec 23 - Dec 26
found 2 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
7.8/10 Good! (1,005 reviews)
The room was not cleaned during the stay. The behaviour of the lady at the reception was very rude and aggressive.
Terrible customer service experience
Reviewed on Nov 12, 2025
4 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was ¥371,466, price is now ¥260,622 per person
¥260,622
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥402,036, price is now ¥316,946 per person
¥316,946
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18.8/10 Exceptional! (1,771 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.
Reviewed on Nov 14, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥383,892, price is now ¥316,307 per person
¥316,307
per person
Dec 23 - Dec 27
found 13 hours ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
