Southern Wisconsin Kid friendly Holidays

Book a Kid friendly Hotel + Flight or Car together to unlock savings

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Top flight + Kid friendly hotel deals in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

Downtown Chicago
£969
per person
22 Nov - 29 Nov
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,460
per person
20 Nov - 26 Nov
found 11 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on 29 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£998
per person
22 Nov - 29 Nov
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£1,040
per person
22 Nov - 29 Nov
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,012
per person
20 Nov - 27 Nov
found 11 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (2,172 reviews)
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5* Kid friendly holidays in Southern Wisconsin

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
£1,460
per person
20 Nov - 26 Nov
found 11 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on 29 Sept 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,977
per person
23 Nov - 27 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£2,907
per person
17 Nov - 24 Nov
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
See all available trips from Edinburgh to Southern Wisconsin
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3 Night Kid friendly holidays in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

Downtown Chicago
£971
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,283
per person
17 Dec - 20 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on 29 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,016
per person
23 Dec - 26 Dec
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Don't see what you're looking for?
See all available trips from Edinburgh to Southern Wisconsin
View all trips

4 Night Kid friendly holidays in Southern Wisconsin

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

Hotel Riu Plaza Chicago

Downtown Chicago
£1,113
per person
29 Oct - 2 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,763
per person
30 Nov - 4 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Trump hotel is right in the middle of downtown, but it's on the quieter side of the river from the other hotels. It offers direct access to the river where you can join the architecture river tour and is overall quieter than the hotels on the other side of the river. The self parking is a bit of a tricky drive up very narrow and curving ramps. If you drive a Suburban or a Cybertruck, you might have difficulty.

Reviewed on 29 Sept 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£1,140
per person
19 Nov - 23 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,156 reviews)
Don't see what you're looking for?
See all available trips from London to Southern Wisconsin
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FAQs: family holidays in Southern Wisconsin

How can I find the best family-friendly holidays in Southern Wisconsin?

At Expedia, it’s super-easy to find family-friendly holidays in Southern Wisconsin 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 Southern Wisconsin 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, Southern Wisconsin family getaways start at £969. Prices and availability are subject to change and additional terms may apply.

Can I book an all-inclusive Southern Wisconsin 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 Southern Wisconsin and book the whole package in just a few clicks.

How can I book the best family activity holiday in Southern Wisconsin?

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 Southern Wisconsin?

To treat the kids to a luxury holiday they’ll never forget, take a look at the most indulgent hotels and resorts in Southern Wisconsin 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 Southern Wisconsin family holiday deals?

Start by entering your dates, then use the family-friendly filter to narrow down your search to show the best available Southern Wisconsin 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 Southern Wisconsin 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 Southern Wisconsin 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 Southern Wisconsin in no time.

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.