Far North Side Cheap Vacations

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Flight and Cheap hotel deals in Far North Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,345
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on Aug 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,752
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.

Reviewed on Aug 17, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
CA $1,900
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
There need to be more paper-cup for coffee-machine.

Reviewed on Aug 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,501
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
CA $1,785
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
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5* Cheap holidays in Far North Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,345
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on Aug 16, 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
CA $2,934
per person
Nov 7 - Nov 12
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
CA $3,806
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around

Reviewed on Aug 16, 2026

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3 Night Cheap holidays in Far North Side

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Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
CA $1,018
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Friendly Staff

Reviewed on Aug 17, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,345
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on Aug 16, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
CA $1,293
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,145 reviews)
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4 Night Cheap holidays in Far North Side

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

Swissotel - Chicago

Downtown Chicago
CA $1,322
per person
Sep 24 - Sep 28
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,787
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.

Reviewed on Aug 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,603
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

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Cheap Hotels in Far North Side

Heart O' Chicago

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. ...
Heart O' Chicago
See all 5,053 properties in Far North Side
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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $38
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Far North Side

More vacations you might like

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