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Northwest Side All inclusive Holidays

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    Packages with flights are ATOL protected

Top All-inclusive holiday packages in Northwest Side

Price found within the past 48 hours. Click for updated prices.
  • 20 Jan - 24 Jan

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,007 reviews)
    "I was surprised by the $29.50 daily charge for "Guest Amenity Fee". I did not ask for it. I don't even know what it is. I hate when hotels charge you hidden items."
    Reviewed November 9, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £898
    £720
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • 25 Dec - 30 Dec

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,082 reviews)
    "Amazing experience! Kurtis and Luis at concierge was great! I had a romantic arrangement in the room before arrival and they made it happen! Great great great 5 ✨"
    Reviewed November 9, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 2 stops
    £1,797
    £1,324
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • 20 Jan - 24 Jan

    Pendry Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,091
    £819
    per traveller
    found 1 day ago
    Pendry Chicago
  • 11 Jan - 16 Jan

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

    Downtown Chicago
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,012 reviews)
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • 1 stop
    £1,079
    £841
    per traveller
    found 2 days ago
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
  • 20 Jan - 24 Jan

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,310 reviews)
    Return • London (LON) - Chicago (ORD)
    LHR - ORD • 1 stop ORD - LHR • 1 stop
    £1,202
    £956
    per traveller
    found 1 day ago
    Viceroy Chicago

Discover the most popular places to visit in Northwest Side

All-inclusive Northwest Side holidays: everything you need to know

Can I book Northwest Side all-inclusive holidays with airfare and meals?

Use the all-inclusive filter to find amazing all-inclusive package holidays to Northwest Side, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset.

Why should I book a Northwest Side adults-only all-inclusive holiday?

If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Northwest Side and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday.

Can I book last minute all-inclusive holidays to Northwest Side?

Last-minute breaks are a great way to find very cheap all-inclusive holidays to Northwest Side. If you can be flexible with your holiday dates, browse our best Northwest Side deals and use the all-inclusive filter to add everything that makes your hols perfect.

Can I book a cheap all-inclusive Northwest Side trip?

There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Northwest Side. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at £720 – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply.

What should I look for when booking a 5-star all-inclusive holiday to Northwest Side?

All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine.

What should I consider when booking a Northwest Side all-inclusive family holiday?

If you’re holidaying with tots in tow, book an all-inclusive Northwest Side package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind.

How can I find the best deals on all-inclusive holidays to Northwest Side in 2026/2027?

There are great all-inclusive deals galore in Northwest Side. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices.

Can I book an all-inclusive Northwest Side package with free cancellation and/or flexible dates?

Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks.

Why should I book an all-inclusive Northwest Side package holiday with Expedia?

With a huge range of all-inclusive Northwest Side trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here.