Far North Side Ski Holidays

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Photo by W. Ross Wells
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Top flight + Ski hotel deals in Far North Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£923
per person
22 Nov - 29 Nov
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
£1,389
per person
7 Nov - 14 Nov
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,418
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
tout était parfait 10/10

Reviewed on 22 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,262
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Great stay!

Reviewed on 22 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£983
per person
22 Nov - 29 Nov
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
It was ok

Reviewed on 21 Sept 2026

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5* Ski holidays in Far North Side

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

Nobu Hotel Chicago

Downtown Chicago
£1,592
per person
28 Nov - 2 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (922 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,857
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
A great experience from check in to check out!

Reviewed on 22 Sept 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,418
per person
22 Oct - 28 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Don't see what you're looking for?
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3 Night Ski holidays in Far North Side

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£890
per person
22 Oct - 25 Oct
found 4 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Great stay!

Reviewed on 22 Sept 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
£902
per person
22 Oct - 25 Oct
found 4 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (3,881 reviews)
.

Reviewed on 22 Sept 2026

Stay One Chicago

Stay One Chicago

Downtown Chicago
£1,078
per person
22 Oct - 25 Oct
found 4 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
7.8/10 Good! (12 reviews)
Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on 20 Sept 2026

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4 Night Ski holidays in Far North Side

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

Level Chicago Fulton Market

Downtown Chicago
£1,161
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!

Reviewed on 21 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,306
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
tout était parfait 10/10

Reviewed on 22 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,315
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
It was ok

Reviewed on 21 Sept 2026

Don't see what you're looking for?
See all available trips from London to Far North Side
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Planning your Far North Side ski holiday

How can I book the best ski holiday to Far North Side in 2026/2027?

Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in Far North Side. 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 Far North Side ski holidays?

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Far North Side 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 £890. Prices and availability are subject to change. Additional terms may apply.

Can I book last-minute ski holidays to Far North Side?

Use our handy last-minute deals page to look for ski holidays to Far North Side 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 Far North Side?

Far North Side 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 Far North Side?

All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in Far North Side. 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 Far North Side?

Ski season in Far North Side 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 Far North Side 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 Far North Side 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 Far North Side that offer it.

Why should I book a ski holiday package in Far North Side 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

£23
per adult
98% of travellers recommend
Flyover in Chicago
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 North Side

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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.