A curved pathway with a metal fence, flowering trees, and a street lamp.

Northwest Side Luxury Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    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

Top Luxury holiday packages in Northwest Side

Price found within the past 48 hours. Click for updated prices.
  • 25 Dec - 30 Dec

    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,000 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £874
    £712
    per traveller
    found 1 day ago
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,073 reviews)
    "i love it"
    Reviewed November 10, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,790
    £1,319
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 25 Dec - 30 Dec

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,580 reviews)
    "Very good"
    Reviewed November 11, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,007
    £804
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • 25 Dec - 30 Dec

    The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.6/10 - Exceptional (1,000 reviews)
    "The hotel lobby and rooftop are nice but the rooms are okay. We had 3 rooms and the shower pressure was terrible in all. The king room felt small so we switched to 2 queens which was much better. The service was so good though and it’s attached to a mall. It was good overall but probably won’t stay here again."
    Reviewed October 29, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,414
    £1,144
    per traveller
    found 1 day ago
    The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
  • 25 Dec - 30 Dec

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,892 reviews)
    "Everything was perfect"
    Reviewed November 11, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,008
    £820
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

Discover the most popular places to visit in Northwest Side

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 £712. 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.