Far North Side All inclusive Holidays

Book a All inclusive Hotel + Flight or Car together to unlock savings

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    Packages with flights are ATOL protected

Top flight + All inclusive hotel deals in Far North Side

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

£943
per person
27 Oct - 2 Nov
found 4 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (391 reviews)
Great experience and will be back at some point!

Reviewed on 18 Sept 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,895
per person
27 Oct - 2 Nov
found 4 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Staff was excellent.

Reviewed on 17 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£2,239
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
£1,308
per person
27 Oct - 2 Nov
found 4 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,835 reviews)
Clean rooms. PLenty of elevators pool was difficult having to go through locker room to enter

Reviewed on 19 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
£2,056
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
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5* All inclusive holidays in Far North Side

Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,895
per person
27 Oct - 2 Nov
found 4 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
Staff was excellent.

Reviewed on 17 Sept 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£2,899
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£2,281
per person
16 Nov - 18 Nov
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home

Reviewed on 19 Sept 2026

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3 Night All inclusive holidays in Far North Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£941
per person
12 Nov - 15 Nov
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
It is amazing

Reviewed on 19 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,095
per person
12 Nov - 15 Nov
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home

Reviewed on 19 Sept 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£993
per person
12 Nov - 15 Nov
found 7 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
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4 Night All inclusive holidays in Far North Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£2,027
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
It is amazing

Reviewed on 19 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£2,251
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home

Reviewed on 19 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£2,239
per person
12 Nov - 16 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
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All-inclusive Far North Side holidays: everything you need to know

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

Use the all-inclusive filter to find amazing all-inclusive package holidays to Far North 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 Far North Side adults-only all-inclusive holiday?

If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Far North 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 Far North Side?

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

Can I book a cheap all-inclusive Far North Side trip?

There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Far North 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 £941 – 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 Far North 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 Far North Side all-inclusive family holiday?

If you’re holidaying with tots in tow, book an all-inclusive Far North 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 Far North Side in 2026/2027?

There are great all-inclusive deals galore in Far North 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 Far North 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 Far North Side package holiday with Expedia?

With a huge range of all-inclusive Far North 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.

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 Far North 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.