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.

![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 $728

per person

Apr 10 - Apr 13

found 15 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Clean and nice room, fantastic breakfast. Nice iced vanilla latte from the 1st level bar area. About the only bad thing i can say was it would have been nice to know that after going in the room I had to insert my room key in the wall to have lights and power.

Reviewed on Feb 2, 2026

![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Banque Hotel

CA $956

per person

Apr 23 - Apr 28

found 22 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (447 reviews)

Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 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 $1,060

per person

Mar 5 - Mar 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on Jan 24, 2026

![Hyatt Centric Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

CA $1,107

per person

Apr 23 - Apr 28

found 22 hours ago

Roundtrip flight included

Montreal (YUL) to Chicago (ORD)

9/10 Wonderful! (1,034 reviews)

Yes, staff was great, hotel was great, the oat meal on the breakfast buffet was the best I have ever had. I crave it. Thank you for making our visit to Chicago wonderful!

Reviewed on Jan 21, 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 $1,030

per person

Apr 23 - Apr 28

found 12 hours ago

Roundtrip flight included

Montreal (YUL) 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 Far North Side

[View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-03-02/2026-03-09/?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.

![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 $1,060

per person

Mar 5 - Mar 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on Jan 24, 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 $1,883

per person

Mar 19 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) 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

![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 $1,848

per person

Mar 19 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Chicago (ORD)

9.8/10 Exceptional! (1,001 reviews)

Staff was wonderful.

Reviewed on Jan 25, 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/2026-03-02/2026-03-09/?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.

![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 $728

per person

Apr 10 - Apr 13

found 15 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Clean and nice room, fantastic breakfast. Nice iced vanilla latte from the 1st level bar area. About the only bad thing i can say was it would have been nice to know that after going in the room I had to insert my room key in the wall to have lights and power.

Reviewed on Feb 2, 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 $1,060

per person

Mar 5 - Mar 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on Jan 24, 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 $1,008

per person

Mar 13 - Mar 16

found 13 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Clean, nice amenities and great staff.

Reviewed on Feb 1, 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/2026-03-02/2026-03-09/?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.

![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 $820

per person

Apr 9 - Apr 13

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Clean and nice room, fantastic breakfast. Nice iced vanilla latte from the 1st level bar area. About the only bad thing i can say was it would have been nice to know that after going in the room I had to insert my room key in the wall to have lights and power.

Reviewed on Feb 2, 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 $836

per person

Apr 25 - Apr 29

found 19 hours ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Great stay. Would come again.

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 $1,631

per person

Mar 19 - Mar 23

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

The room was boring thought it would be cleaner updated for the price best part was the view

Reviewed on Jan 24, 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/2026-03-02/2026-03-09/?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! (1,002 reviews)

Great

Reviewed on Feb 1, 2026

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

[See all 5,445 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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