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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
CA $864
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.6/10 Excellent! (1,012 reviews)
Midland hotel was clean and tidy, and the staff were accommodating, friendly, and helpful throughout our stay. We had a pleasant experience and would definitely return in the future!

Reviewed on Oct 5, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
CA $1,211
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,447
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $988
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Great hotel in the perfect location as everything is walking distance. Rooms are very clean and comfortable. Breakfast buffet is great. Only issue i had with the stay was the rooftop bar. Thought this was going to be a great spot to overlook the city but the view was average. Service at the bar was very poor. Went there a couple times with the first time we didnt get a server to come to our table for the first 15-20 mins of being there so I had to walk up to the bar to get my own drink. The second time we sat at a table and server took our drink orders but after 20 minutes of waiting for my drink to come out i had to speak with a manager. The manager was great at that point and was very apologetic and comped our drinks. Overall this was great stay but was very expensive 4 day trip.

Reviewed on Oct 5, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
Save 100% on your flight
CA $1,444
per person
Dec 13 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,156 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
Save 100% on your flight
CA $1,447
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
CA $1,764
per person
Nov 15 - Nov 18
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
CA $1,901
per person
Nov 27 - Nov 30
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
It was such a joy to stay at the Park Hyatt for our wedding! The staff at the Hyatt went above and beyond to make our stay memorable. It was all fabulous from the staff, to the food, to the beautiful views.

Reviewed on Oct 1, 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 $995
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,447
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,263
per person
Nov 27 - Nov 30
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,156 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Northwest Side
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4 Night Luxury 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
Save 100% on your flight
CA $1,261
per person
Nov 19 - Nov 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Great hotel in the perfect location as everything is walking distance. Rooms are very clean and comfortable. Breakfast buffet is great. Only issue i had with the stay was the rooftop bar. Thought this was going to be a great spot to overlook the city but the view was average. Service at the bar was very poor. Went there a couple times with the first time we didnt get a server to come to our table for the first 15-20 mins of being there so I had to walk up to the bar to get my own drink. The second time we sat at a table and server took our drink orders but after 20 minutes of waiting for my drink to come out i had to speak with a manager. The manager was great at that point and was very apologetic and comped our drinks. Overall this was great stay but was very expensive 4 day trip.

Reviewed on Oct 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,805
per person
Nov 19 - Nov 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
CA $1,299
per person
Nov 12 - Nov 16
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
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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 $864, 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 28. 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
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $59
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.