Title: West Loop Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $857 Expedia.ca

[West Loop Travel Guide](https://expedia.ca/Chicago-West-Loop.dx553248634029130868)[Hotels in West Loop](https://expedia.ca/West-Loop-Chicago-Hotels.0-n553248634029130868-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[West Loop Car Rentals](https://expedia.ca/Car-Rentals-In-West-Loop.d553248634029130868.Car-Rental-Guide)

![](https://images.trvl-media.com/place/553248634029130868/e4d15962-627f-4352-9768-bd3b891abed4.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# West Loop Vacation Packages

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

- ##  
Plan, book, travel with confidence
- ###  
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
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in West Loop

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

![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

CA $857

per person

Jun 5 - Jun 8

found 2 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

8.4/10 Very Good! (1,014 reviews)

But the parking 23$ omg

Reviewed on Mar 29, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,298

per person

May 14 - May 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

Clean room , staff are friendly , breakfast is amazing just the rooftop bar was closed due to the winter season

Reviewed on Mar 31, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $978

per person

May 8 - May 11

found 13 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (441 reviews)

The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing

Reviewed on Mar 27, 2026

![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/69dc07eb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Viceroy Chicago

Downtown Chicago

CA $1,546

per person

May 26 - May 30

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,187 reviews)

Very nice place on the Gold Coast!

Reviewed on Mar 23, 2026

![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Warwick Allerton - Chicago

Downtown Chicago

CA $1,094

per person

May 14 - May 17

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

8.6/10 Excellent! (3,039 reviews)

Requested additional towels, never came. Luggage racks were difficult to obtain. Rooms are small. Bring your own hairdryer. Water pressure in shower is minimal.

Reviewed on Mar 27, 2026

## Where to stay in West Loop

Find the best West Loop areas and neighborhoods for the activities you enjoy most. [Learn more about West Loop](https://expedia.ca/Chicago-West-Loop.dx553248634029130868)

![Downtown Chicago](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Chicago

5 out of top 10 points of interest in this area

 The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. 

[Find hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Magnificent Mile](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

 Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. 

[Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Loop](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(733 area reviews)

 Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. 

[Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### O'Hare

3.5/5(39 area reviews)

 Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates. 

[Find hotel + flight trips in O'Hare](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=O%27Hare&DestID=553248635074842747&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![River North](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### River North

 Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. 

[Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## West Loop Hotel Deals

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Emily Hotel

311 North Morgan Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $237

CA $278 total

Apr 5 - Apr 6

includes taxes & fees

9.2/10 Wonderful! (1,335 reviews)

Place was very nice.

Reviewed on Mar 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=19381112&PinnedHotelID=19381112&HadPinnedHotel=true&regionId=553248634029130868)

![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/871940a9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street Chicago IL

Fully refundable

CA $182

CA $214 total

Apr 30 - May 1

includes taxes & fees

9/10 Wonderful! (2,044 reviews)

Yes parking felt safe

Reviewed on Mar 30, 2026

[](https://expedia.ca/Hotel-Search?startDate=30%2F04%2F2026&endDate=01%2F05%2F2026&selected=1293276&PinnedHotelID=1293276&HadPinnedHotel=true&regionId=553248634029130868)

![Holiday Inn & Suites Chicago - Downtown by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/9b3b5e62_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn & Suites Chicago - Downtown by IHG

506 West Harrison Street Chicago IL

Fully refundable

CA $159

CA $203 total

Apr 5 - Apr 6

includes taxes & fees

8.6/10 Excellent! (1,009 reviews)

The room was clean with no issues. Very limited parking on site, but there is a parking lot adjacent to the property that isn't associated with the hotel.

Reviewed on Mar 29, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=201274&PinnedHotelID=201274&HadPinnedHotel=true&regionId=553248634029130868)

[See all 4,690 properties in West Loop](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&regionId=553248634029130868)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a West Loop vacation package cost?

### How do I get a cheap travel package to West Loop?

### Where should I stay in West Loop?

### What are the top hotels in West Loop?

### How far in advance should I book my West Loop vacation?

### What does an Expedia West Loop travel package include?

### What should I know before booking a West Loop travel package?

### Can I choose my airline with a West Loop Expedia vacation package?

### If I'm not able to travel, can I cancel my West Loop vacation package?

### Things to do

![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 360 CHICAGO Observation Deck

CA $37

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details)

![Art Institute of Chicago](https://mediaim.expedia.com/localexpert/170360/cfa59fea-c028-46b9-93be-ea78b723f52e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Art Institute of Chicago

CA $55

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/art-institute-of-chicago.a170360.activity-details)

![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago: Navy Pier Centennial Wheel Ticket

CA $34

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details)

[See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=553248634029130868)

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