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

![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Northwest Side Cheap Vacations

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## Flight and Cheap hotel deals in Northwest Side

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

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $845

per person

Apr 1 - Apr 6

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

8.2/10 Very Good! (2,365 reviews)

Liked the neat and tidy room I was assigned to. They accommodated my request for the shower. Staff showed great hospitality special thanks to Sasha, Konnor, Rigel. Would have been greater had there been more amenities like body lotion, sleeper, toothbrush, etc.

Reviewed on Jan 7, 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 $1,125

per person

Apr 1 - Apr 6

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

everything was awesome. The room was amazing. The staff was very helpful. The entire hotel was very clean. The only drawback was the water pressure in the sink. We had a room with two sinks, and both sinks had low water, pressure and lukewarm water. It never did get hot.

Reviewed on Jan 19, 2026

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $1,070

per person

Apr 1 - Apr 6

found 23 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

Room was extremely clean, and staff was very accommodating

Reviewed on Jan 17, 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 $1,124

per person

Apr 1 - Apr 6

found 20 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Clean room and amenities

Reviewed on Jan 8, 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 $1,727

per person

Apr 3 - Apr 8

found 7 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing

Reviewed on Jan 13, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Cheap holidays in Northwest Side

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

![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 $1,263

per person

Mar 2 - Mar 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Yes didn’t know you get free breakfast

Reviewed on Jan 4, 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 $1,727

per person

Apr 3 - Apr 8

found 7 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing

Reviewed on Jan 13, 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 $2,251

per person

Apr 3 - Apr 8

found 7 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on Jan 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Cheap holidays in Northwest Side

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

![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 $831

per person

Apr 7 - Apr 10

found 9 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 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 $1,028

per person

Apr 2 - Apr 5

found 16 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

everything was awesome. The room was amazing. The staff was very helpful. The entire hotel was very clean. The only drawback was the water pressure in the sink. We had a room with two sinks, and both sinks had low water, pressure and lukewarm water. It never did get hot.

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 $1,555

per person

Mar 21 - Mar 24

found 4 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on Jan 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Cheap holidays in Northwest 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 $730

per person

Apr 13 - Apr 17

found 8 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

everything was awesome. The room was amazing. The staff was very helpful. The entire hotel was very clean. The only drawback was the water pressure in the sink. We had a room with two sinks, and both sinks had low water, pressure and lukewarm water. It never did get hot.

Reviewed on Jan 19, 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 $1,482

per person

Mar 12 - Mar 16

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing

Reviewed on Jan 13, 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 $1,193

per person

Mar 12 - Mar 16

found 6 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-19/2026-02-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

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## More Vacations Ideas

[Flights to Northwest Side

](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[

Northwest Side Hotels

](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[

Northwest Side Vacation Rentals

](https://expedia.ca/Northwest-Side-Vacation-Rentals.d553248635976475367.Travel-Guide-VacationRentals)[

Northwest Side Car Rentals

](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[

Northwest Side Vacations

](https://expedia.ca/Northwest-Side.d553248635976475367.Destination-Travel-Guides)

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

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