Title: Cheap Vacations in Far North Side 2026 | Expedia.ca

![](https://images.trvl-media.com/place/553248635074842747/4c830a7f-a9f5-4e29-83f7-dc2e54b474ac.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Far North Side Cheap Vacations

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Photo by W. Ross Wells

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## Flight and Cheap hotel deals in Far North Side

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

![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 $874

per person

Mar 13 - Mar 17

found 17 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Everything was exceptional!!!!!

Reviewed on Jan 6, 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 $896

per person

Mar 13 - Mar 17

found 17 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Everything is ok but no parking lot and too much fee

Reviewed on Jan 6, 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 $989

per person

Mar 13 - Mar 17

found 17 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

![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 $2,408

per person

Mar 13 - Mar 20

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!

Reviewed on Jan 6, 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 $1,178

per person

Mar 13 - Mar 16

found 11 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Far North Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Cheap holidays in Far North Side

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

![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 $1,170

per person

Feb 13 - Feb 16

found 10 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Room was excellent. Everything was clean and the amenities were fantastic. Staff was very warm and helpful. Will go back

Reviewed on Jan 2, 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 $2,408

per person

Mar 13 - Mar 20

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!

Reviewed on Jan 6, 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 $1,178

per person

Mar 13 - Mar 16

found 11 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Far North Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Cheap holidays in Far North Side

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

![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 $788

per person

Apr 3 - Apr 6

found 16 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

Perfect location, comfortable and clean room

Reviewed on Jan 5, 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 $849

per person

Apr 3 - Apr 6

found 16 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Everything is ok but no parking lot and too much fee

Reviewed on Jan 6, 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 $1,178

per person

Mar 13 - Mar 16

found 11 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

Don't see what you're looking for?

See all available trips from Columbus to Far North Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Cheap holidays in Far North Side

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

![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 $874

per person

Mar 13 - Mar 17

found 17 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Everything was exceptional!!!!!

Reviewed on Jan 6, 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 $896

per person

Mar 13 - Mar 17

found 17 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Everything is ok but no parking lot and too much fee

Reviewed on Jan 6, 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 $989

per person

Mar 13 - Mar 17

found 17 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Don't see what you're looking for?

See all available trips from Columbus to Far North Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-07/2026-02-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## Cheap Hotels in Far North Side

![Heart O' Chicago](https://images.trvl-media.com/lodging/2000000/1670000/1669700/1669633/4e6864c7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Heart O' Chicago

5990 North Ridge Ave Chicago IL

- 16 min walk from Loyola University Chicago

Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...

7.6/10 Good! (1,000 reviews)

Very nice

Reviewed on Dec 24, 2025

[](https://expedia.ca/Chicago-Hotels-Heart-O-Chicago.h1669633.Hotel-Information)

[See all 5,313 properties in Far North Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248635976475356)

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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## More Vacations Ideas

[Flights to Far North Side

](https://expedia.ca/Cheap-Flights-To-Far-North-Side.d553248635976475356.Travel-Guide-Flights)[

Far North Side Hotels

](https://expedia.ca/Far-North-Side-Hotels.d553248635976475356.Travel-Guide-Hotels)[

Far North Side Vacation Rentals

](https://expedia.ca/Far-North-Side-Vacation-Rentals.d553248635976475356.Travel-Guide-VacationRentals)[

Far North Side Car Rentals

](https://expedia.ca/Car-Rentals-In-Far-North-Side.d553248635976475356.Car-Rental-Guide)[

Far North Side Vacations

](https://expedia.ca/Far-North-Side.d553248635976475356.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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