Northwest Side Luxury 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 Luxury hotel deals in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,069
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
👍

Reviewed on Sep 28, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,089
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
It was great great great !

Reviewed on Sep 28, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,083
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Wonderful rooms and great views

Reviewed on Sep 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,344
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go. There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable. We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles. Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult. The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.

Reviewed on Sep 28, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,130
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
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5* Luxury 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
CA $1,089
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
It was great great great !

Reviewed on Sep 28, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
CA $2,032
per person
Oct 29 - Nov 1
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
CA $1,814
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on Sep 24, 2026

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3 Night Luxury 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
CA $964
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,344
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go. There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable. We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles. Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult. The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.

Reviewed on Sep 28, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,130
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
View all trips

4 Night Luxury holidays in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $991
per person
Dec 10 - Dec 14
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
👍

Reviewed on Sep 28, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,077
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Clean room but there was no basic supplies beyond soap, shampoo and conditioner. And coffee (expresso). We were not allowed to request a wine glass in our room, just plastic cups. Breakfast was great but they did not supply paper cups to take a cup of coffee to go. There was a refrigerator but hardly worked. It was difficult to figure out how to use the shower. The 2 double beds we had were pushed together. Would have preferred separation of the double beds. However the beds were comfortable. We were only left water 2 nights of the 4 we stayed and had to ask for it on day 2. There were no water filling stations anywhere in the hotel for water bottles. Difficult to operate the TV remote. Took us a while to figure it out - no instructions. I don’t know why everything had to be so difficult. The staff was not overly friendly except for the valet guy. He always made a point to check in with us, ask where we were going and offer advice. I thought place was overly priced for what we got. Location was great but I would not stay again at this hotel.

Reviewed on Sep 28, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,889
per person
Dec 23 - Dec 27
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
It was great great great !

Reviewed on Sep 28, 2026

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Plan the perfect luxury Northwest Side vacation with Expedia

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 $964, 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 27. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Northwest Side

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.