Far Southeast Side Kid friendly Holidays

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Top flight + Kid friendly hotel deals in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£883
per person
24 Oct - 28 Oct
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,004
per person
14 Oct - 20 Oct
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on 10 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,041
per person
24 Oct - 28 Oct
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,120
per person
24 Oct - 28 Oct
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
It was clean but not a fan of the old carpet.

Reviewed on 10 Aug 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£1,395
per person
17 Sept - 21 Sept
found 24 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
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5* Kid friendly holidays 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
£1,666
per person
12 Oct - 16 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
This place was crazy amazing!!!! Positioned perfectly in heart of Downtown Chicago! You are so close to everything! Customer service was top tier! They treated my family with so much care and everyone was so kind!!! We will absolutely return and stay again when we make our way back to Chicago! Thank you Trump Tower for an amazing stay!

Reviewed on 10 Aug 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,004
per person
14 Oct - 20 Oct
found 6 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on 10 Aug 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,159
per person
12 Oct - 16 Oct
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.8/10 Exceptional! (1,008 reviews)
The staff and hotel was fantastic

Reviewed on 10 Aug 2026

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3 Night Kid friendly holidays in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£826
per person
5 Nov - 8 Nov
found 4 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,055
per person
5 Nov - 8 Nov
found 4 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
This place was crazy amazing!!!! Positioned perfectly in heart of Downtown Chicago! You are so close to everything! Customer service was top tier! They treated my family with so much care and everyone was so kind!!! We will absolutely return and stay again when we make our way back to Chicago! Thank you Trump Tower for an amazing stay!

Reviewed on 10 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£887
per person
5 Nov - 8 Nov
found 4 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Don't see what you're looking for?
See all available trips from London to Far Southeast Side
View all trips

4 Night Kid friendly holidays in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£883
per person
24 Oct - 28 Oct
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,282
per person
10 Sept - 14 Sept
found 24 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,120
per person
24 Oct - 28 Oct
found 14 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
It was clean but not a fan of the old carpet.

Reviewed on 10 Aug 2026

Don't see what you're looking for?
See all available trips from Dublin to Far Southeast Side
View all trips

FAQs: family holidays in Far Southeast Side

How can I find the best family-friendly holidays in Far Southeast Side?

At Expedia, it’s super-easy to find family-friendly holidays in Far Southeast Side in our vast inventory. Use our handy filters to find hotels and resorts with the best reviews, most amenities and lowest price tags. You can also hunt out great flights and smashing deals on car hire, so you can book the whole shebang in one place.

Are there any cheap Far Southeast Side family holidays?

Avoid forking out for multiple hotel rooms by booking a villa or apartment with a kitchen and give your brood plenty of space and all the meals they love at a fraction of the cost. Find the most affordable family holidays by filtering your search by price. Generally, Far Southeast Side family getaways start at £826. Prices and availability are subject to change and additional terms may apply.

Can I book an all-inclusive Far Southeast Side family holiday package?

All-inclusive holidays can keep the costs down when you’re travelling as a family. Think unlimited mocktails for the little'uns and double doses of gin for the bigguns. Use our all-inclusive filter to see what’s available in Far Southeast Side and book the whole package in just a few clicks.

How can I book the best family activity holiday in Far Southeast Side?

Family holidays are all about spending quality time together, laughing, playing and bonding as you try new things. Pack your trip full of family activities they’ll love and make memories that’ll last a lifetime.

Can I find luxury family holidays in Far Southeast Side?

To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Far Southeast Side by using our 5-star filter. To really travel in style, use the first-class filter to find the best flights, too.

How can I search for Far Southeast Side family holiday deals?

Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Far Southeast Side family holiday deals. If your travel dates are flexible, play around to see if you can find cheaper options or more availability at different times.

Can I book a Far Southeast Side family vacation package with free cancellation and/or flexible dates?

Plans change, so booking a family holiday with free cancellation is a great way to ensure you don’t lose out if they do. Use the fully refundable and reserve now pay later filters to find flexibility. Make sure you always check terms and conditions, too.

Why should I book my Far Southeast Side family trip with Expedia?

Forget family fights and start thinking about family flights. Our huge selection of easy to browse family-friendly holidays means you can find and book your dream family trip to Far Southeast Side in no time.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Far Southeast Side

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.