Great River Road Luxury Holidays

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Top flight + Luxury hotel deals in Great River Road

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
£1,212
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
First time staying here and we were not disappointed at all. We were upgraded to a two room suite and the view was spectacular! Beds were super comfortable with soft bedding and the room had everything we needed. The staff were all really friendly and helpful as well. Would definitely stay again.

Reviewed on 21 Aug 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£1,340
per person
13 Oct - 20 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Excellent front desk staff. Great place, very clean with a touch of everyday luxury. Highly recommend!

Reviewed on 21 Aug 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
£1,373
per person
13 Oct - 20 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (518 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,237
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Incredible hotel — it was clean, the room was spacious, the staff were incredibly friendly, and it was conveniently located in the heart of downtown, within walking distance of everything we needed.

Reviewed on 21 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,555
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
It’s amazing view from the window! All my family love it! Clean and cozy !

Reviewed on 21 Aug 2026

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5* Luxury holidays in Great River Road

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

The Mayfair

French Quarter
£1,539
per person
10 Nov - 17 Nov
found 1 day ago
Return flight included
London (LON) to New Orleans (MSY)
10/10 Exceptional! (42 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,555
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
It’s amazing view from the window! All my family love it! Clean and cozy !

Reviewed on 21 Aug 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£2,102
per person
9 Oct - 13 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
The AC in the room did not work and made our stay miserable . When asked for a refund the hotel disregarded the request and advised they can help us next time. Our stay was not pleasant at all as we sweat all night and our room was very humid .

Reviewed on 21 Aug 2026

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4 Night Luxury holidays in Great River Road

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
£1,212
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
First time staying here and we were not disappointed at all. We were upgraded to a two room suite and the view was spectacular! Beds were super comfortable with soft bedding and the room had everything we needed. The staff were all really friendly and helpful as well. Would definitely stay again.

Reviewed on 21 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,237
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Incredible hotel — it was clean, the room was spacious, the staff were incredibly friendly, and it was conveniently located in the heart of downtown, within walking distance of everything we needed.

Reviewed on 21 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,555
per person
27 Sept - 1 Oct
found 7 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
It’s amazing view from the window! All my family love it! Clean and cozy !

Reviewed on 21 Aug 2026

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All you need to know about luxury holidays in Great River Road

What can I expect from a luxury Great River Road holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Great River Road?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Great River Road holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Great River Road?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Great River Road starting at £1,212. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Great River Road?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Great River Road spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Great River Road?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Great River Road?

You can wangle a top-notch luxury holiday in Great River Road for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Great River Road with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Great River Road with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Great River Road to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

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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.