Luxury Vacations in Northwest Side 2026

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Flight and Luxury hotel deals in Northwest Side

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

Sheraton Grand Chicago Riverwalk

Downtown Chicago

CA $1,125

per person

Jan 2 - Jan 5

found 19 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

8.6/10 Excellent! (1,841 reviews)

It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop

Reviewed on Oct 19, 2026

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

CA $1,159

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

CA $1,336

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Victoria Resort and Bed & Breakfast

North Side

CA $1,785

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.6/10 Exceptional! (154 reviews)

This is a lovely place to stay with great amenities and special touches. The breakfast was amazing! Highly recommend this gem just 2 blocks from the beach and easy bike ride to downtown. The owner is onsite and very friendly.

Reviewed on Oct 10, 2026

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

Downtown Chicago

CA $1,598

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Great location and staff

Reviewed on Oct 12, 2026

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5* Luxury holidays in Northwest Side

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

Park Hyatt Chicago

Downtown Chicago

CA $1,591

per person

Dec 11 - Dec 13

just found

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.6/10 Exceptional! (1,003 reviews)

The service was truly outstanding. Every member of the staff was welcoming, professional, attentive, and genuinely committed to making our stay memorable. Our room was absolutely beautiful—spacious, impeccably maintained, elegantly designed, and extremely comfortable. The quality of the accommodations exceeded our expectations. The food was equally impressive, with delicious dishes, excellent presentation, and wonderful service. Every dining experience was a pleasure. What really sets this hotel apart is the combination of its beautiful property, exceptional hospitality, and the attention given to every little detail. It’s the kind of place that makes you feel genuinely appreciated as a guest.

Reviewed on Oct 19, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,964

per person

Dec 27 - Dec 31

found 12 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

The Peninsula Chicago

Downtown Chicago

CA $2,305

per person

Dec 27 - Dec 31

found 12 hours ago

Roundtrip flight included

Vancouver (YVR) to Chicago (ORD)

9.8/10 Exceptional! (1,015 reviews)

Loved the hotel

Reviewed on Oct 15, 2026

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3 Night Luxury holidays in Northwest Side

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

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

CA $765

per person

Dec 1 - Dec 4

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (2,274 reviews)

Good location, small rooms,

Reviewed on Oct 20, 2026

The Talbott, Autograph Collection

Downtown Chicago

CA $847

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $1,754

per person

Dec 5 - Dec 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

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4 Night Luxury holidays in Northwest Side

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

The Talbott, Autograph Collection

Downtown Chicago

CA $878

per person

Dec 16 - Dec 20

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $1,833

per person

Nov 21 - Nov 25

found 17 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Sheraton Grand Chicago Riverwalk

Downtown Chicago

CA $1,023

per person

Nov 25 - Nov 29

found 12 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

8.6/10 Excellent! (1,841 reviews)

It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop

Reviewed on Oct 19, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

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What are some benefits when booking luxury Northwest Side vacations?

When you book a luxury Northwest Side vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Northwest Side?

If you're looking for something luxurious in Northwest Side, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $765, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 20. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Northwest Side. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Northwest Side?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Northwest Side.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Northwest Side. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Northwest Side?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Northwest Side or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Northwest Side. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.