Far Southeast Side Kid friendly Vacations

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Top Kid friendly vacation packages in Far Southeast Side

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

Swissotel - Chicago

Downtown Chicago
¥259,686
per person
Sep 9 - Sep 12
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Hotel is in a great spot! We loved everything about our stay except the fact the lobby bar closes at 11 on a Saturday night! 8.5/10

Reviewed on Aug 10, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥292,022
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥347,696
per person
Oct 10 - Oct 13
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
The hotel is located at the very end of Navy Pier and uncomfortable for reaching the city center. Check-in was long and the staff was unpleasant. Our toilet didn’t work and the room was dirty. Chicago is filled with hotel options. Skip this one.

Reviewed on Aug 10, 2026

Sentral Michigan Avenue

Sentral Michigan Avenue

Downtown Chicago
¥494,270
per person
Sep 14 - Sep 21
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,237 reviews)
We went to a concert at Northerly Island and this was a perfect location. Lots of things to do in the area and restaurants everywhere. The park being right across the street was great since we brought our dogs with us too!

Reviewed on Aug 10, 2026

Freehand Chicago

Freehand Chicago

Downtown Chicago
¥279,254
per person
Sep 17 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (3,233 reviews)
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5* Kid friendly vacations in Far Southeast Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥359,747
per person
Sep 20 - Sep 23
found 16 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
¥396,135
per person
Sep 20 - Sep 23
found 16 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
We had a terrific weekend stay! The staff was so friendly and the room was wonderful with a very comfortable bed. Location is very convenient, as well.

Reviewed on Aug 10, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥455,954
per person
Sep 20 - Sep 23
found 16 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
The staff and hotel was fantastic

Reviewed on Aug 10, 2026

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3 Night Kid friendly vacations in Far Southeast Side

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
¥286,388
per person
Sep 17 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,879 reviews)
Gym was awesome. First time in Chicago. This was a great place to stay: wish there was more of a bar scene / restaurant but still great.

Reviewed on Aug 10, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥291,068
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥347,696
per person
Oct 10 - Oct 13
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
The hotel is located at the very end of Navy Pier and uncomfortable for reaching the city center. Check-in was long and the staff was unpleasant. Our toilet didn’t work and the room was dirty. Chicago is filled with hotel options. Skip this one.

Reviewed on Aug 10, 2026

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4 Night Kid friendly vacations in Far Southeast Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
¥265,134
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥360,552
per person
Sep 18 - Sep 22
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Hotel is in a great spot! We loved everything about our stay except the fact the lobby bar closes at 11 on a Saturday night! 8.5/10

Reviewed on Aug 10, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
¥277,842
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
The staff was amazing and the dining next door was just as amazing! 10/10 would stay again.

Reviewed on Aug 10, 2026

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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

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