Great River Road Ski Holidays

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Top flight + Ski hotel deals in Great River Road

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£833
per person
23 Oct - 28 Oct
found 20 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
We had a wonderful two day stay at Hotel St Clair. The room was clean and the bathroom provided complimentary shampoo/conditioner. The staff were friendly and allowed for us to check out an hour later than usual. It was our second time staying at this hotel and we will definitely return when we visit Chicago again. My only recommendation to the property would be to add a water dispenser in the lobby for guests, so we do not have to go to the gym.

Reviewed on 12 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
£1,084
per person
23 Oct - 28 Oct
found 20 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,072
per person
2 Oct - 6 Oct
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Everything was extremely great.

Reviewed on 13 Aug 2026

The Eleanor New Orleans

The Eleanor New Orleans

New Orleans Central Business District
Save 100% on your flight
£2,286
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LON) to New Orleans (MSY)
9.2/10 Wonderful! (93 reviews)
Wonderful stay! It was within walking distance of everything we wanted to do. The host was prompt in getting back to us when needed. We had a great time in New Orleans with no worries about housing. Thanks for checking one box off our list of concerns.

Reviewed on 11 Aug 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£2,453
per person
8 Oct - 13 Oct
found 16 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
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5* Ski 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
Save 100% on your flight
£1,429
per person
23 Oct - 28 Oct
found 20 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The service and rooms were excellent. Beds were comfortable and views were to die for. The food at Terra16 was a good but the wait times and food service took to long. Our fruit platter took over a half hour for breakfast. The spa was nice, but the lockers were hard to use or some worked and some did not lock. Front desk was exceptional and property was gorgeous. I would definitely stay again and was very happy with the staff who generally were attentive and kind.

Reviewed on 13 Aug 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£2,140
per person
8 Oct - 12 Oct
found 10 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
incredible staff and stay here. The team here crushed it and the rooms were fantastic

Reviewed on 12 Aug 2026

Four Seasons Hotel Minneapolis

Four Seasons Hotel Minneapolis

Downtown Minneapolis
£1,739
per person
5 Nov - 9 Nov
found 1 day ago
Return flight included
London (LGW) to Minneapolis (MSP)
9.6/10 Exceptional! (350 reviews)
Every last detail was perfect. Amenities are impressive and service was warm and gracious. Every single person we encountered was genuine and helpful. Pool is such a great vibe!

Reviewed on 8 Aug 2026

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3 Night Ski holidays in Great River Road

Price found within the past 48 hours. Click for updated prices.
Sheraton New Orleans Hotel

Sheraton New Orleans Hotel

New Orleans Central Business District
£589
per person
2 Oct - 5 Oct
found 10 hours ago
Return flight included
London (LON) to New Orleans (MSY)
8.8/10 Excellent! (1,672 reviews)
New Orleans Marriott

New Orleans Marriott

French Quarter
£596
per person
2 Oct - 5 Oct
found 10 hours ago
Return flight included
London (LON) to New Orleans (MSY)
9/10 Wonderful! (1,964 reviews)
I love everything about this property, and the outstanding customer service was the icing on the cake. I will definitely be booking with them again!

Reviewed on 10 Aug 2026

Le Méridien New Orleans

Le Méridien New Orleans

New Orleans Central Business District
£592
per person
2 Oct - 5 Oct
found 10 hours ago
Return flight included
London (LON) to New Orleans (MSY)
8.6/10 Excellent! (2,279 reviews)
Nice view!!

Reviewed on 13 Aug 2026

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4 Night Ski holidays in Great River Road

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£998
per person
2 Oct - 6 Oct
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on 12 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,072
per person
2 Oct - 6 Oct
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Everything was extremely great.

Reviewed on 13 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,215
per person
2 Oct - 6 Oct
found 15 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Rooms were decent. The view was the best part. Overall was alright, wouldn’t say the best experience.

Reviewed on 12 Aug 2026

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Planning your Great River Road ski holiday

How can I book the best ski holiday to Great River Road in 2026/2027?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Great River Road. Just choose your dates and see what’s available. You might prefer a hotel with a heated outdoor pool, or a private chalet for après ski parties; either way, use the property filters to your ideal match. If ski-in-ski-out is important, use the map view to find those idyllic slopeside properties.

How can I find cheap Great River Road ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Great River Road accommodation a little further from the lifts and go self-catering to cut back on eating out. Sort your search results by price to find options from £589. Prices and availability are subject to change. Additional terms may apply.

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

Use our handy last-minute deals page to look for ski holidays to Great River Road at a steal. If your dates are fixed, simply input the details and see what specials are available.

What should I consider when booking family ski holidays in Great River Road?

Great River Road is well set up for kids. For the teeniest ski-woks, day care in the snow is a blast. As they get older, they love whizzing around on the hill in ski school. Choose a hotel near the lifts and nursery slopes to save a whole lot of ski-carrying hassle in the mornings. With all that extra time and energy, you can take your sweet time to find a family-favourite bolthole on the mountain for hot chocolate with marshmallows ski breaks.

Can I book all-inclusive ski holidays to Great River Road?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Great River Road. If not, consider booking your flights and accommodation together to save money that way instead.

When's the best time of year to plan a ski trip to Great River Road?

Ski season in Great River Road generally starts around December and slopes off around April. Keep an eye on the snow forecasts though, as you can often find some brilliant deals at the start or end of the season, when it’s also much quieter.

How can I find the best deals on Great River Road ski holiday packages?

If you can be flexible with your ski holiday dates, avoid school holidays and instead buckle up your boots at the start or end of season. Sort your search results by price and look out for self-catered accommodation to save on notoriously expensive ski-resort drinking and dining.

Can I book a Great River Road ski trip with free cancellation and/or flexible dates?

If you’re not 100% sure on plans or just want peace of mind, choose a ski holiday with free cancellation. You can use our free cancellation filter to find properties in Great River Road that offer it.

Why should I book a ski holiday package in Great River Road with Expedia?

Schuss your way to the slopes with Expedia’s smooth booking process. From flights to hotels and even car hire, you’ll find everything you need to plan the ultimate winter wonderland ski holiday.

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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.