Far North Side Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Far North Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was CA $1,157, price is now CA $830 per person
CA $830
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very good! (3,941 reviews)
Very charming hotel. Loved the art deco bathroom! The room was large for an old inner city hotel. Plus you cannot beat the location!! So reasonably priced too. Definitely would stay again.

Reviewed on Jul 1, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,038, price is now CA $1,377 per person
CA $1,377
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on Jul 2, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,608, price is now CA $1,112 per person
CA $1,112
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on Jul 2, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,758, price is now CA $1,256 per person
CA $1,256
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Great property in the heart of the city

Reviewed on Jul 1, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,415, price is now CA $1,015 per person
CA $1,015
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Traveling as a family of 4 with 2 teenagers and we could not have picked a better place to stay. We were able to see all the sights, eat all the Chicago food and shop until we dropped. I would absolutely stay here again.

Reviewed on Jul 3, 2026

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 Riviera Theatre or Aragon Ballroom and hop on the metro to see more the city at Western Station (Brown Line) or Rockwell Station.

Find hotels in Lincoln Square

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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 $172 per night from Jul 6 to Jul 7
CA $172
CA $205 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on Jul 2, 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jul 5 to Jul 6
CA $217
CA $305 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (1,835 reviews)
"Traveling as a family of 4 with 2 teenagers and we could not have picked a better place to stay. We were able to see all the sights, eat all the Chicago food and shop until we dropped. I would absolutely stay here again."

Reviewed on Jul 3, 2026

Omni Chicago Hotel
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 $240 per night from Jul 5 to Jul 6
CA $240
CA $273 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (2,760 reviews)
"The hotel location was next to the blue line station the property was clean and all the staff was nice and helpful"

Reviewed on Jul 3, 2026

Hyatt Regency O'Hare Chicago
See all 4,950 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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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 acclaimed theater scene.
See properties

What to do in Far North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
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
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago 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 $830. 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.

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