Save up to £750 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Packages with flights are ATOL protected
Discover the most popular places to visit in West Side
United Center
8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
University of Illinois Chicago
8.4/10 (1,058 reviews)
Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.
Humboldt Park
7.0/10 (2 reviews)
Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed art galleries and entertainment choices in this vibrant area.
Garfield Park Conservatory
9.0/10 (6 reviews)
While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.
Credit Union 1 Arena
8.0/10 (5 reviews)
Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Anna and Frederick Douglass Park
7.0/10 (12 reviews)
After visiting Anna and Frederick Douglass Park, make a plan to see the other sights and activities in Chicago. Experience the fascinating museums and entertainment choices in this vibrant area.
The Salt Shed
You can get tickets for a performance at The Salt Shed on your trip to Chicago. Experience the live music and theatre scene in this vibrant area.
Union Park
After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
"A super cute hotel in a great walkable neighborhood. Only downside is they are very strict about check in/check out times. Also the walls between rooms are thin. Our neighbors were having a super fun time which was great for them, but kept us awake throughout the night."
"Front desk staff
Every front desk person was friendly and helpful
Room
Spacious and Recently updated
Location
Proximity to CTA is perfect or walkable to attractions, Grant Park etc
Amenities
5 stars for on site washer dryer. First time I've ever seen this at a hotel"
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
How can I book the best ski holiday to West Side in 2026/2027?
Search through alpine adventures on Expedia to plan your perfect snowy ski holiday in West 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 West Side ski holidays?
Boot hire, lift passes, lessons: ski holidays can get pricey, quickly. To make your ski trip more affordable, book West 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 £1,218. Prices and availability are subject to change. Additional terms may apply.
Can I book last-minute ski holidays to West Side?
Use our handy last-minute deals page to look for ski holidays to West 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 West Side?
West 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 West Side?
All-inclusive ski holidays are fairly rare, but you can use our filter to see if there are any available in West 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 West Side?
Ski season in West 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 West 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 West 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 West Side that offer it.
Why should I book a ski holiday package in West 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.