Title: Luxury Vacations in Illinois 2026 | Expedia.ca

![](https://images.trvl-media.com/place/215/aa920d34-e093-4af5-87ef-8a5ae8eefcac.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Illinois Luxury Vacations

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
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Better together  
Save up to CA $1,096 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
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Rest easy  
Plan, book, and manage your trip all in one place

## Flight and Luxury hotel deals in Illinois

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

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

CA $751

per person

Feb 22 - Feb 27

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (3,392 reviews)

Great service. Thoughtful management sent us chocolates for our anniversary. Beautiful rooms, daily room refresh, awesome rooftop and views. Helpful staff. Loved everything.

Reviewed on Dec 19, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,017

per person

Jan 21 - Jan 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

From staff to room it was a amazing experience.

Reviewed on Dec 18, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,254

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

![Omni Chicago Hotel](https://images.trvl-media.com/lodging/1000000/20000/11100/11076/433c2c13_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Omni Chicago Hotel

Downtown Chicago

CA $979

per person

Mar 15 - Mar 19

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,603 reviews)

Perfect location in the heart of the Magnificent Mile. Great holiday ambiance

Reviewed on Dec 17, 2025

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $1,129

per person

Jan 30 - Feb 2

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

It is always an amazing place to stay

Reviewed on Nov 26, 2025

Don't see what you're looking for?

See all available trips from Columbus to Illinois

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Luxury holidays in Illinois

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

![Chicago Athletic Association, a Hyatt Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

CA $1,119

per person

Feb 25 - Mar 1

found 9 hours ago

Roundtrip non-stop flight included

St. John's (YYT) to Chicago (ORD)

9/10 Wonderful! (1,000 reviews)

It’s amazing historical property

Reviewed on Dec 15, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,409

per person

Feb 11 - Feb 15

found 9 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

From staff to room it was a amazing experience.

Reviewed on Dec 18, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $1,762

per person

Feb 11 - Feb 15

found 9 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

Don't see what you're looking for?

See all available trips from Columbus to Illinois

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Plan the perfect luxury Illinois vacation with Expedia

####  What are some benefits when booking luxury Illinois vacations? 

When you book a luxury Illinois 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 Illinois? 

If you're looking for something luxurious in Illinois, 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 $751, 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 19\. 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 Illinois. 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 Illinois? 

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 Illinois.

####  Can I book last-minute luxury vacations? 

Yes, last-minute bookings are often available in Illinois. 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 Illinois? 

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 Illinois 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 Illinois. 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.

## Luxury Hotels in Illinois

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Trump International Hotel & Tower Chicago

401 N Wabash Ave Chicago IL

- 5 min walk from Michigan Avenue

CA $386

CA $454 total

Jan 4 - Jan 5, 2026

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

9.4/10 Exceptional! (1,787 reviews)

From staff to room it was a amazing experience.

Reviewed on Dec 18, 2025

[](https://expedia.ca/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information)

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Langham, Chicago

330 North Wabash Avenue Chicago IL

- 5 min walk from Michigan Avenue

CA $557

CA $654 total

Jan 11 - Jan 12, 2026

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

9.6/10 Exceptional! (1,004 reviews)

Everything was great!

Reviewed on Dec 17, 2025

[](https://expedia.ca/Chicago-Hotels-The-Langham.h6309326.Hotel-Information)

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Peninsula Chicago

108 East Superior Street Chicago IL

- 6 min walk from Michigan Avenue

CA $614

CA $721 total

Jan 10 - Jan 11, 2026

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...

9.6/10 Exceptional! (1,009 reviews)

Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing

Reviewed on Dec 16, 2025

[](https://expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information)

[See all 10,431 properties in Illinois](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=215)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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