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.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£918
per person
21 Nov - 25 Nov
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.

Reviewed on 26 Sept 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£1,116
per person
3 Nov - 8 Nov
found 24 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
Amazing stay for a family of four. The kids loved the pool, and the adults loved the hot tub! It felt close to the action, without being too close. Quiet but walkable to Navy Pier, Michigan Avenue, etc. Nearby multiple grocery stores. The building was well maintained and the neighborhood felt safe. The views from the room were unbelievable (the pictures don't do them justice). I would definitely stay here again.

Reviewed on 26 Sept 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£1,671
per person
16 Nov - 20 Nov
found 21 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Sentral Michigan Avenue

Sentral Michigan Avenue

Downtown Chicago
£1,090
per person
3 Nov - 8 Nov
found 24 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (1,336 reviews)
Crean room

Reviewed on 26 Sept 2026

Stay One Chicago

Stay One Chicago

Downtown Chicago
£1,353
per person
3 Nov - 8 Nov
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
7.8/10 Good! (12 reviews)
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on 20 Sept 2026

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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
£1,202
per person
3 Nov - 6 Nov
found 12 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Fabulous location with amazing river views!

Reviewed on 27 Sept 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£1,671
per person
16 Nov - 20 Nov
found 21 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,823
per person
16 Nov - 20 Nov
found 21 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
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3 Night Kid friendly holidays 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
£948
per person
3 Nov - 6 Nov
found 12 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
El hotel es muy funcional. Está muy bien ubicado. Excelentes habitaciones con cero ruido que facilitan el descanso. Muy recomendable lugar!

Reviewed on 27 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,202
per person
3 Nov - 6 Nov
found 12 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Fabulous location with amazing river views!

Reviewed on 27 Sept 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£981
per person
3 Nov - 6 Nov
found 12 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
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4 Night Kid friendly holidays 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
£853
per person
21 Nov - 25 Nov
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
El hotel es muy funcional. Está muy bien ubicado. Excelentes habitaciones con cero ruido que facilitan el descanso. Muy recomendable lugar!

Reviewed on 27 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,255
per person
21 Nov - 25 Nov
found 21 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Fabulous location with amazing river views!

Reviewed on 27 Sept 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£1,671
per person
16 Nov - 20 Nov
found 21 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
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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 £853. 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

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.