Far Southwest Side Ski Holidays

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Top flight + Ski hotel deals in Far Southwest Side

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£795
per person
1 Oct - 6 Oct
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (2,079 reviews)
Perfect location

Reviewed on 7 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,055
per person
1 Oct - 6 Oct
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,406
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£992
per person
1 Oct - 6 Oct
found 18 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Great staff, great place!

Reviewed on 5 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
£1,780
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Don't see what you're looking for?
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5* Ski holidays in Far Southwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,278
per person
8 Sept - 11 Sept
found 16 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Great experience!

Reviewed on 7 Aug 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,406
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£2,523
per person
9 Oct - 15 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
Don't see what you're looking for?
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3 Night Ski holidays in Far Southwest Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£963
per person
7 Sept - 10 Sept
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
£972
per person
10 Sept - 13 Sept
found 20 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,150 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,027
per person
7 Sept - 10 Sept
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Don't see what you're looking for?
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4 Night Ski holidays in Far Southwest Side

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

Swissotel - Chicago

Downtown Chicago
£1,054
per person
9 Sept - 13 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,127
per person
25 Sept - 29 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£1,514
per person
8 Oct - 12 Oct
found 14 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Don't see what you're looking for?
See all available trips from London to Far Southwest Side
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Planning your Far Southwest Side ski holiday

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

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

Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book Far Southwest 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 £795. Prices and availability are subject to change. Additional terms may apply.

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

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

Far Southwest 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 Southwest Side?

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

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

Why should I book a ski holiday package in Far Southwest 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
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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 Southwest 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.