Far North Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by W. Ross Wells

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Far North Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,164, price is now CA $795 per person
CA $795
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,858 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,642, price is now CA $1,029 per person
CA $1,029
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
It was lovely!!

Reviewed on Jul 29, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,678, price is now CA $1,168 per person
CA $1,168
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)
Comes with all the comforts of Home.

Reviewed on Jul 29, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,496, price is now CA $1,077 per person
CA $1,077
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Great hotel and the staff was amazing

Reviewed on Jul 29, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,722, price is now CA $1,276 per person
CA $1,276
per person
Sep 25 - Sep 28
found 14 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,502 reviews)

Where to stay in Far North Side

Find the best Far North Side areas and neighborhoods for the activities you enjoy most. Learn more about Far North Side
A sign for Lincoln Square with a red brick building in the background.

Lincoln Square

When in Lincoln Square and the surrounding area, you'll want to check out sights like Swedish American Museum Center or Riviera Theatre and hop on the metro to see more the city at Western Station (Brown Line) or Rockwell Station.

Find hotels in Lincoln Square

Ready to book your vacation to Far North Side?

 

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Far North Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Aug 13 to Aug 14
CA $240
CA $285 total
Aug 13 - Aug 14
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Aug 9 to Aug 10
CA $240
CA $285 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (1,857 reviews)
"Booked this hotel, thought it was going to be nice based on the photos. Was disappointed to say the least. Upon arrival, the front desk charged an additional $143 to check in. They did not offer a receipt for that charge. We get our room key and send us up to our room and there’s only 1 bed. Go back ..."

Reviewed on Jul 29, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $281 per night from Aug 6 to Aug 7
CA $281
CA $320 total
Aug 6 - Aug 7
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 5,038 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.
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All Inclusive Vacations
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Beach Vacations
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Stay near popular Far North Side attractions

A historic theater with ornate architecture and a prominent marquee.

Aragon Ballroom

9.2/10 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
See properties

What to do in Far North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
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 $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Far North Side

Frequently asked questions

How much does a Far North Side vacation package cost?
Tailor make your Far North Side vacation package from only CA $795. Pick from any combination of rental cars, flights and hotels to build the getaway you've been dreaming about. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Far North Side?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all. Pick a combination that suits you and see your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 properties throughout the world, which lets you customize your Far North Side getaway.
How far in advance should I book my Far North Side vacation?
It can be tricky to know when the best time is to book your Far North Side vacation. But usually the earlier you book, the cheaper the prices. In some cases, you can reserve your flights and hotels up to a year prior to departure. If you're thinking of a last-minute getaway, no need to stress! There are fantastic bargains announced on Expedia every day.
What does an Expedia Far North Side travel package include?
From flights and hotels to car rentals, Expedia can help you put together a Far North Side package that's perfect for you. Vacationing for a few weeks? Check out a rental car, hotel and flight bundle. If your break is short, a hotel and airfare deal could be more your style. Experiences can also be added after you've booked. Our travel packages make it simple to plan and save.
What should I know before booking a Far North Side travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Far North Side Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Far North Side vacation package?
Your situation can change unexpectedly, so yes. You may be able to change or cancel your Far North Side vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Explore a world of travel with Expedia

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