Far North Side Vacation Packages

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Top Far North Side Vacation Deals

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,363, price is now CA $842 per person
CA $842
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Corner room with breath taking view. It was my second time in this hotel, it never disappoints.

Reviewed on Apr 27, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,780, price is now CA $1,054 per person
CA $1,054
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,882 reviews)
The HVAC was annoying AF. It would go on and blow cold air for 10 minutes, then be off for 15-20 minutes repeatedly. It is so loud, it kept waking me up through out the night. As a short person, I did not like the fact the bed was a challenge to get on top. Not everyone is five feet tall.

Reviewed on Apr 26, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was CA $2,140, price is now CA $1,398 per person
CA $1,398
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Wonderful Hotel will definitely be looking forward to going back.

Reviewed on Apr 25, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,578, price is now CA $1,040 per person
CA $1,040
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (466 reviews)
Nice and easy process

Reviewed on Apr 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 $1,754, price is now CA $1,174 per person
CA $1,174
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,458 reviews)
Great week-long stay. We loved the king corner room - the views were fantastic. Room was large and comfortable. All staff were really accommodating.

Reviewed on Apr 29, 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
www.alamy.com

Lincoln Square

1 out of top 10 points of interest in this area

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

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Far North Side Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from May 25 to May 26
CA $119
CA $183 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,646 reviews)
Great location nice hotel!

Reviewed on Apr 28, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $185 per night from May 26 to May 27
CA $185
CA $220 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,135 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it

Reviewed on Apr 29, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundable
The price is CA $150 per night from May 25 to May 26
CA $150
CA $178 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,479 reviews)
Great check in and check out experience

Reviewed on Apr 29, 2026

Club Quarters Hotel, Central Loop, Chicago
See all 5,227 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Far North Side

Chicago_AragonBallroom_553248621563220754

Aragon Ballroom

Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Aragon Ballroom
Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes

What to do in Far North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Far North Side

Frequently asked questions

Can I cancel my flight booking to Far North Side due to COVID-19?
Our Customer Service Portal is your one-stop shop for most travel queries, including about flight changes and cancellations related to COVID-19. For more peace of mind, we suggest reading through the terms and conditions of your preferred carrier before booking.
What's the best way to find cheap flights to Far North Side that have flexible change policies?
We know that plans can change in a flash, so choosing a flexible fare with Expedia is a wise idea. Just check the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to Far North Side is just a few clicks away.
What are some of the general tips for travelers to Far North Side during the COVID-19 outbreak?
COVID-19 has led to substantial changes to the way we travel. If you plan to jet off to Far North Side, these tips will help you navigate these new challenges and rules:
  • Understand the restrictions and rules in both your destination and origin. You may not be able to travel depending on local circumstances, so don't forget to check before you lock in your flight.
  • When you go through airport checkpoints, keep your face mask on. You will be asked to lower it briefly for identification purposes. Travelers who refuse to wear a mask may face civil penalties and may also be escorted from the building.
  • Avoid handing your boarding pass directly to a TSA officer. Rather, you should place the pass on the reader and then hold it up so the agent can inspect it.
  • You are now permitted to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. This will need to be removed for X-ray screening.
  • Place any personal items (like your phone and wallet) in your carry-on rather than a bin to minimize handling during screening.
  • Transport your food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to touch and open your bag for inspection.

Which airlines fly to Far North Side?
American Airlines offers flights into or near Far North Side, including 13307 that fly into O'Hare Intl. Airport (ORD) each month. Choose your travel dates and then reserve your airfare early for an awesome deal.
How can I find cheap tickets to Far North Side?
One of the best ways to bag cheap tickets to Far North Side is to be flexible with your dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The lowest price for a flight to Far North Side in the last seven days was . Booking well ahead of time will usually help you get an even better deal.
How much is a flight to Far North Side?
If you were journeying one way from (), you could've snapped up a cheap ticket for just in the last seven days. Return flights to Far North Side ranged from to over the same period.
What are the most popular airports to fly into in Far North Side?
Fly into O'Hare Intl. Airport (ORD) and sample everything that Far North Side has to offer. As the region's primary entry point, approximately 33491 flights land here each month.
When is the cheapest time to fly to Far North Side?
If you can be flexible with what date you travel to Far North Side, fly out earlier in the week. The most affordable day to take off is normally Tuesday, closely followed by Monday. Saturday is typically the priciest day, with many people preferring to fly on the weekend.
How much is a plane ticket to Far North Side?
Flights to Far North Side ranged from to in the last seven days. Usually, the sooner you book the bigger the bargain.
Which airlines with flights to Far North Side employ COVID-19 cleanliness policies?
As passengers and cabin crew start traveling once again, the majority of airlines have implemented physical distancing and other vital measures to help lessen the spread of COVID-19. Here are just some of them:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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.