Northwest Side All inclusive Holidays

Book a All inclusive 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 flight + All inclusive 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
£802
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. So much to do in walking distance and hotel was great.

Reviewed on 16 Sept 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,364
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£975
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,039
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.2/10 Wonderful! (2,169 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£872
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Don't see what you're looking for?
See all available trips from Glasgow to Northwest Side
View all trips

5* All inclusive holidays in Northwest 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
£1,364
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
£1,625
per person
10 Dec - 15 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£2,525
per person
26 Oct - 31 Oct
found 17 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The hotel is located in a prime location with shops and restaurants nearby. The staff was very accommodating and helpful.

Reviewed on 15 Sept 2026

Don't see what you're looking for?
See all available trips from Glasgow to Northwest Side
View all trips

3 Night All inclusive 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
£996
per person
1 Dec - 4 Dec
just found
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. So much to do in walking distance and hotel was great.

Reviewed on 16 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,117
per person
24 Oct - 27 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
£1,242
per person
24 Oct - 27 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
The gym was great. The noise from the road was very loud.

Reviewed on 15 Sept 2026

Don't see what you're looking for?
See all available trips from London to Northwest Side
View all trips

4 Night All inclusive holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£860
per person
26 Nov - 30 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,005
per person
26 Nov - 30 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. So much to do in walking distance and hotel was great.

Reviewed on 16 Sept 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,120
per person
1 Nov - 5 Nov
found 4 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I was excited to stay here and I truly never leave negative reviews, but others should avoid making the same mistake I did paying for this hotel. The staff was very nice and the property looks nice, but it's extremely overpriced. Don't be fooled into paying more for the amenities because none of them work!! - There was no deadbolt on the hotel room door. If I'm paying $200+ a night, I shouldn't have to barricade the door every night. The balcony door was also unlocked when I arrived. - No hangers or lotion in the room. - Sauna and hot tub were "closed for cleaning" for three full days of my stay. - I needed to consent to a background check in order to confirm my reservation. I called to confirm this because I found it incredibly invasive and unnecessary. Turns out it was real. Wild. Also, there is a $200 PER NIGHT deposit upon arrival. I travel often and I've never seen that before. - Nonexistent water pressure in the shower. And someone's trash was left in the shower when I arrived. - Washing machine reeked of mold and was therefore unusable. - TV and oven didn't work Overall, if this hotel was $60-80 a night, it'd be great. But, it's a total waste of money. Again, the staff was very nice and helpful (I didn't even include the things they resolved for me during my stay) but I'm not going to bother them about every single amenity that is supposedly included with the room. The things that would make this hotel worth the money are unfortunately all a facade.

Reviewed on 15 Sept 2026

Don't see what you're looking for?
See all available trips from London to Northwest Side
View all trips

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 £802 – 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.

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 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.