Far Southwest Side Kid friendly Holidays

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Top flight + Kid friendly hotel deals in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£729
per person
7 Nov - 12 Nov
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy

Reviewed on 19 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,159
per person
7 Nov - 12 Nov
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Amazing hotel. We go every year and always have a great time. We were greeted with a warm hand towel and champagne.

Reviewed on 19 Aug 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
£931
per person
7 Nov - 12 Nov
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
£940
per person
7 Nov - 12 Nov
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful room & View!! Will definitely book again!

Reviewed on 19 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£773
per person
7 Nov - 12 Nov
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
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5* Kid friendly holidays in Far Southwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,159
per person
7 Nov - 12 Nov
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Amazing hotel. We go every year and always have a great time. We were greeted with a warm hand towel and champagne.

Reviewed on 19 Aug 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
Save 100% on your flight
£1,501
per person
7 Nov - 12 Nov
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£3,409
per person
20 Sept - 25 Sept
found 1 day ago
Return flight included
London (LHR) 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 16 Aug 2026

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3 Night Kid friendly holidays in Far Southwest Side

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£435
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Austin (AUS) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
Very nice place to stay. Rooms were just a bit on the smaller side.

Reviewed on 19 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£558
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

Downtown Chicago
£446
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.2/10 Wonderful! (2,768 reviews)
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4 Night Kid friendly holidays in Far Southwest 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
£873
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Great staff, very clean property. Enjoyed the café for lattes and cocktails! Breakfast is a fair price for being additional. I loved the location many bars and restaurants just a few minutes walk away.

Reviewed on 19 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,133
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,026
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LON) 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 17 Aug 2026

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FAQs: family holidays in Far Southwest Side

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

At Expedia, it’s super-easy to find family-friendly holidays in Far Southwest 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 Southwest 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 Southwest Side family getaways start at £435. Prices and availability are subject to change and additional terms may apply.

Can I book an all-inclusive Far Southwest 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 Southwest Side and book the whole package in just a few clicks.

How can I book the best family activity holiday in Far Southwest 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 Southwest 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 Southwest 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 Southwest 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 Southwest 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 Southwest 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 Southwest 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 Southwest 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 Southwest 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.