Northwest Side Luxury Holidays

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    Packages with flights are ATOL protected

Top flight + Luxury hotel deals in Northwest Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£699
per person
7 Dec - 10 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Breakfast, clean room, Staff

Reviewed on 27 Sept 2026

Stay One Chicago

Stay One Chicago

Downtown Chicago
£1,683
per person
17 Nov - 24 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) 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

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

Downtown Chicago
£935
per person
17 Nov - 24 Nov
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,567 reviews)
.

Reviewed on 26 Sept 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£745
per person
7 Dec - 10 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
£777
per person
7 Dec - 10 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Don't see what you're looking for?
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5* Luxury holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£8,635
per person
16 Nov - 21 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£9,037
per person
16 Nov - 21 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£8,875
per person
16 Nov - 21 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Don't see what you're looking for?
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3 Night Luxury holidays in Northwest Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£699
per person
7 Dec - 10 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Breakfast, clean room, Staff

Reviewed on 27 Sept 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£745
per person
7 Dec - 10 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
£777
per person
7 Dec - 10 Dec
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Don't see what you're looking for?
See all available trips from Manchester to Northwest Side
View all trips

4 Night Luxury holidays in Northwest Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£853
per person
21 Nov - 25 Nov
found 3 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Breakfast, clean room, Staff

Reviewed on 27 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,255
per person
21 Nov - 25 Nov
found 3 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£1,671
per person
16 Nov - 20 Nov
found 3 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Don't see what you're looking for?
See all available trips from London to Northwest Side
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All you need to know about luxury holidays in Northwest Side

What can I expect from a luxury Northwest 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 Northwest Side?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Northwest 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 Northwest 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 Northwest Side starting at £699. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Northwest Side?

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

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

Nobody does luxury quite like Expedia. With so many gorgeous properties in Northwest 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

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Northwest Side

More holidays you might like

* 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.