Title: Cheap Vacations in West Side 2026 | Expedia.ca

![](https://images.trvl-media.com/place/829/ad657303-bbed-4f45-9ba5-b7c23d3e76f3.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# West Side Cheap Vacations

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

Photo by throwingsofas

- ##  
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

## Flight and Cheap hotel deals in West Side

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

![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 $598

per person

Apr 17 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Everything was amazing, specially the breakfast buffet.

Reviewed on Feb 7, 2026

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $930

per person

Mar 21 - Mar 27

found 4 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### JW Marriott Chicago

Downtown Chicago

CA $707

per person

May 1 - May 3

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.2/10 Wonderful! (1,000 reviews)

Bottle of waters were not stocked in the refrigerator.

Reviewed on Jan 6, 2026

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $972

per person

Mar 21 - Mar 27

found 4 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,625

per person

Mar 21 - Mar 27

found 4 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Gorgeous property, facilities, and location.

Reviewed on Feb 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to West Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Cheap holidays in West Side

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

![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 $1,435

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Langham, Chicago

Downtown Chicago

CA $1,625

per person

Mar 21 - Mar 27

found 4 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Gorgeous property, facilities, and location.

Reviewed on Feb 6, 2026

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $1,793

per person

Mar 31 - Apr 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

The staff and amenities

Reviewed on Feb 4, 2026

Don't see what you're looking for?

See all available trips from Columbus to West Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Cheap holidays in West Side

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

![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 $628

per person

Apr 14 - Apr 17

found 1 day ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Everything was amazing, specially the breakfast buffet.

Reviewed on Feb 7, 2026

![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 $1,065

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $636

per person

Apr 14 - Apr 17

found 1 day ago

Roundtrip flight included

Toronto (YTZ) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Great stay. Would come again.

Reviewed on Jan 19, 2026

Don't see what you're looking for?

See all available trips from Columbus to West Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Cheap holidays in West Side

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

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $745

per person

Apr 27 - May 1

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Great stay. Would come again.

Reviewed on Jan 19, 2026

![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 $1,494

per person

Apr 2 - Apr 6

found 9 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.

Reviewed on Jan 26, 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 $819

per person

Apr 27 - May 1

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Everything was amazing, specially the breakfast buffet.

Reviewed on Feb 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to West Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Cheap Hotels in West Side

![Chicago Parthenon Hostel](https://images.trvl-media.com/lodging/34000000/33460000/33450600/33450517/d01ed022_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Chicago Parthenon Hostel

310 S. Halsted Street Chicago IL

- 19 min walk from United Center

Stay at this hostel in Chicago. Enjoy free WiFi, concierge services, and housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions ...

8/10 Very Good! (449 reviews)

This is a great, no-frills hostel situated in between UIC-Chicago and Greektown. The staff is courteous, friendly, and offered great suggestions as to places to see in Chicago. Offering cooking facilities, shared refrigerator, free coffee, tea and a common room to watch tv or use the free wifi, this ...

Reviewed on Jan 18, 2026

[](https://expedia.ca/Chicago-Hotels-Chicago-Parthenon-Hostel.h33450517.Hotel-Information)

![Hyatt House Chicago Medical/University District](https://images.trvl-media.com/lodging/50000000/49320000/49315100/49315022/689da744_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt House Chicago Medical/University District

1835 West Harrison Street Chicago IL

- 10 min walk from United Center

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...

9/10 Wonderful! (1,378 reviews)

The staff working at the front desk were lovely and so helpful! The room was very clean and I enjoyed my stay. I only wished that the lights in the room/bathroom didn't automatically turn off every 20 minutes, that got a little frustrating especially when in the shower.

Reviewed on Feb 6, 2026

[](https://expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-MedicalUniversity-District.h49315022.Hotel-Information)

[See all 898 properties in West Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635976475400)

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.

## More vacations you might like

![](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)

## More Vacations Ideas

[Flights to West Side

](https://expedia.ca/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[

West Side Hotels

](https://expedia.ca/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[

West Side Vacation Rentals

](https://expedia.ca/West-Side-Vacation-Rentals.d553248635976475400.Travel-Guide-VacationRentals)[

West Side Car Rentals

](https://expedia.ca/Car-Rentals-In-West-Side.d553248635976475400.Car-Rental-Guide)[

West Side Vacations

](https://expedia.ca/West-Side.d553248635976475400.Destination-Travel-Guides)[

Things to do in West Side

](https://expedia.ca/Things-To-Do-In-West-Side.d553248635976475400.Travel-Guide-Activities)

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

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app