Northwest Chicago All inclusive Vacations

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    Save up to CA $4,200 when you book a flight and hotel together*
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Flight and All inclusive hotel deals in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
CA $770
per person
Jan 2 - Jan 9
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
Location was great. Front desk staff were friendly and helpful

Reviewed on Oct 26, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
CA $954
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Very nice property. However there were loud drunk college age kids who woke us up repeatedly throughout the night at 4 to 5 am by yelling in the hallway and banging on doors over and over. They also left bags of trash in the hallway near our room. Please up your security

Reviewed on Oct 26, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $973
per person
Jan 2 - Jan 9
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)
The stay was everything I love the view and peaceful. Thank you

Reviewed on Oct 26, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,132
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
This place is great and clean

Reviewed on Oct 26, 2026

Kinzie Hotel

Kinzie Hotel

Downtown Chicago
CA $962
per person
Jan 2 - Jan 9
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,187 reviews)
Friendly, helpful staff. Great accommodations and recommendations, with a central location and easy access to transportation.

Reviewed on Oct 25, 2026

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5* All inclusive holidays in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,346
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
Save 100% on your flight
CA $1,961
per person
Dec 29 - Jan 2
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
CA $2,679
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
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3 Night All inclusive holidays in Northwest Chicago

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

The Talbott, Autograph Collection

Downtown Chicago
CA $837
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
It’a a beautiful and charming building with just the right amount of modernity. My room was a tad bit smalller than I’d expected (queen bed) and the view was nonexistent but cozy and comfortable for for a single person. The room came with a fully stocked mini fridge, a Nespresso machine and two very plush bath robes. The staff was very accommodating and friendly. Each day I was there(three), housekeeping was excellent Shopping, dining and spectacular architecture are in ample supply right outside your door. Will definitely stay here when I’m there city!

Reviewed on Oct 26, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
CA $954
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Very nice property. However there were loud drunk college age kids who woke us up repeatedly throughout the night at 4 to 5 am by yelling in the hallway and banging on doors over and over. They also left bags of trash in the hallway near our room. Please up your security

Reviewed on Oct 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,695
per person
Dec 5 - Dec 8
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
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4 Night All inclusive holidays in Northwest Chicago

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

The Talbott, Autograph Collection

Downtown Chicago
CA $1,020
per person
Nov 28 - Dec 2
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
It’a a beautiful and charming building with just the right amount of modernity. My room was a tad bit smalller than I’d expected (queen bed) and the view was nonexistent but cozy and comfortable for for a single person. The room came with a fully stocked mini fridge, a Nespresso machine and two very plush bath robes. The staff was very accommodating and friendly. Each day I was there(three), housekeeping was excellent Shopping, dining and spectacular architecture are in ample supply right outside your door. Will definitely stay here when I’m there city!

Reviewed on Oct 26, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

Downtown Chicago
CA $1,093
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)
Very nice property. However there were loud drunk college age kids who woke us up repeatedly throughout the night at 4 to 5 am by yelling in the hallway and banging on doors over and over. They also left bags of trash in the hallway near our room. Please up your security

Reviewed on Oct 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,870
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
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Embark on an unforgettable all-inclusive trip to Northwest Chicago including airfare with Expedia

What are some benefits of booking an all-inclusive vacation?

When you opt for an all-inclusive vacation to Northwest Chicago, you can have everything you want to do planned out in advance. That means you get to simply coast through your vacation knowing exactly what's coming next. Plus, this helps you get a final tally on the costs beforehand, so it's much easier on your budget.

Can I book all-inclusive packages with airfare and meals?

Yes, all-inclusive vacation packages are readily available for Northwest Chicago, and you can search for them simply by using the search filter for all-inclusivity. When you book your flight along with your accommodations, you may even find some savings, with the potential to save up to 26.

Why should I book Northwest Chicago vacations that are all inclusive and adults only?

Adults-only stays in Northwest Chicago are good for travellers who are looking to relax in laid-back and easygoing surroundings. Everyone in the area will be looking to do much of the same without any kids to worry about, so you can truly take in some time for yourself in pampered bliss. Plus, you can filter for adults-only stays specifically in your search, so they're easy to find.

Can I book all-inclusive packages?

Yes, all-inclusive packages are fairly standard in Northwest Chicago. You can easily find all-inclusive options by using the search filters, but that's just the beginning. If you're booking at the last minute, you may even find additional discounts as properties try to fill their last remaining spots for cheap vacations that are all inclusive.

Can I book cheap all-inclusive trips to Northwest Chicago?

If you're looking to save, you'll find a wide range of prices available, ranging from CA $770. By booking your accommodations and flight together, you may be able to enjoy savings of up to 26. Be sure to sort your search results by price to list the cheapest options first.

What should I look for when booking a 5-star all-inclusive vacation in Northwest Chicago?

If you've implemented the 5-star filter when searching for your all-inclusive vacation in Northwest Chicago, there are a few factors to keep an eye out for. Spa access is particularly popular, as it's one of the best features you'll find in luxury accommodation options. Additionally, you should consider opting for an infinity pool and a luxury suite, especially if you're travelling with a relatively large group.

What should I consider when booking Northwest Chicago vacation packages that are all inclusive for the family?

The most important thing to consider for all-inclusive family vacations to Northwest Chicago is what your family is interested in. If your kids need access to a pool, you'll want to implement the search filter for that amenity. Kids' clubs can also be perfect for your family, as can babysitting services if the adults in your group plan on enjoying Northwest Chicago's nightlife.

How can I find the best deals on all-inclusive vacations in Northwest Chicago?

You can always sort your search results by price to automatically put the cheapest options at the top of your search while still considering all your implemented search filters.

Can I book an all-inclusive package that is fully refundable?

Yes, reservations that are fully refundable are available on some all-inclusive packages in . You can explore each package's cancellation policy in the policy section of their page, where you'll learn exactly how you can qualify. Sometimes, nothing is required to qualify.

Why should I book an all-inclusive vacation with Expedia?

Booking with Expedia makes it easy to find the ultimate all-inclusive vacation package. By offering accommodations and flights together, all-inclusive packages are easy for us to create and for you to enjoy. With benefits like being fully refundable and flexible dates on some packages, you can enjoy a more stree-free booking process. Expedia Rewards members can take that even further with the possibility of additional discounts.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Northwest Chicago

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.