West Side Luxury Holidays

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Top flight + Luxury hotel deals in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£1,136
per person
19 Oct - 26 Oct
found 8 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,509
per person
19 Oct - 26 Oct
found 8 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on 17 Aug 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£1,348
per person
19 Oct - 26 Oct
found 8 hours ago
Return direct flight included
Edinburgh (EDI) 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

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,978
per person
19 Oct - 26 Oct
found 8 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on 16 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
£1,441
per person
19 Oct - 26 Oct
found 8 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
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5* Luxury holidays in West Side

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
£1,978
per person
19 Oct - 26 Oct
found 8 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on 16 Aug 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£2,324
per person
26 Sept - 2 Oct
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,695
per person
26 Sept - 2 Oct
found 8 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
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3 Night Luxury holidays in West Side

Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

Downtown Evanston
£1,028
per person
21 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (99 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
£1,792
per person
21 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Rooms and beds are always so nice. Very calming and always get a good night’s sleep. I’ve always had a great experience. One detail which falls short is the toilet paper is very rough. Aside from this detail everything else surpasses my expectations.

Reviewed on 16 Aug 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare
£1,066
per person
21 Sept - 24 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very good! (2,362 reviews)
Don't see what you're looking for?
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4 Night Luxury holidays in West Side

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

Swissotel - Chicago

Downtown Chicago
£1,250
per person
22 Oct - 26 Oct
found 1 hour ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.

Reviewed on 17 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,297
per person
22 Oct - 26 Oct
found 1 hour ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on 17 Aug 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£1,525
per person
8 Oct - 12 Oct
found 14 hours ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Don't see what you're looking for?
See all available trips from London to West Side
View all trips

All you need to know about luxury holidays in West Side

What can I expect from a luxury West Side 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 West Side?

Tick the all-inclusive and 5-star filters to find the crème de la crème of West Side 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 West Side?

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 West Side starting at £1,028. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in West Side?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal West Side 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 West Side?

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 West Side?

You can wangle a top-notch luxury holiday in West Side 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 West Side 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 West Side with Expedia?

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

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 West Side

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Where to go when
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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.