Great River Road Kid friendly Holidays

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Top flight + Kid friendly hotel deals in Great River Road

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

The Emily Hotel

Downtown Chicago
£728
per person
26 Nov - 30 Nov
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
The Drake

The Drake

Downtown Chicago
£1,450
per person
8 Nov - 12 Nov
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,583 reviews)
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago
£1,478
per person
8 Nov - 12 Nov
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,278 reviews)
The room was clean and the building was nostalgic.

Reviewed on 22 Sept 2026

Omni Chicago Hotel

Omni Chicago Hotel

Downtown Chicago
£1,534
per person
8 Nov - 12 Nov
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,055 reviews)
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,333
per person
15 Dec - 22 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,169 reviews)
The location of the hotel is perfect with easy access to most attractions. The staff was very nice. The room was clean. The facility is a little run down and we did wonder why every time we turn on the light on the bathroom there was a loud noise , it turns out that it was the fan and they do have a sign to notify guests including a night light so you don't have to turn the light on if you are just going in and out. The cocktail reception every day is a plus. I would stay again.

Reviewed on 22 Sept 2026

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5* Kid friendly holidays in Great River Road

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,613
per person
29 Nov - 2 Dec
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£1,682
per person
29 Nov - 2 Dec
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,731
per person
29 Nov - 2 Dec
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
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3 Night Kid friendly holidays in Great River Road

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

Downtown Chicago
£1,466
per person
29 Nov - 2 Dec
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,497
per person
29 Nov - 2 Dec
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The hotel room is clean but blood stain spotted on the bedsheet.

Reviewed on 23 Sept 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£1,522
per person
29 Nov - 2 Dec
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.

Reviewed on 23 Sept 2026

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4 Night Kid friendly holidays in Great River Road

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Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

Downtown Chicago
£1,422
per person
8 Nov - 12 Nov
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (1,567 reviews)
No comp water

Reviewed on 22 Sept 2026

The Drake

The Drake

Downtown Chicago
£1,450
per person
8 Nov - 12 Nov
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,583 reviews)
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago
£1,480
per person
8 Nov - 12 Nov
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (2,039 reviews)
Pool and gym was convenient and clean

Reviewed on 23 Sept 2026

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FAQs: family holidays in Great River Road

How can I find the best family-friendly holidays in Great River Road?

At Expedia, it’s super-easy to find family-friendly holidays in Great River Road 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 Great River Road 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, Great River Road family getaways start at £728. Prices and availability are subject to change and additional terms may apply.

Can I book an all-inclusive Great River Road 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 Great River Road and book the whole package in just a few clicks.

How can I book the best family activity holiday in Great River Road?

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 Great River Road?

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

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

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* 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.