Far North Side Holidays from NZ$2,395

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The Latest Far North Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
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 NZ$2,901, price is now NZ$2,395 per person
NZ$2,395
per person
21 Jan - 26 Jan
found 22 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
Room was clean, staff was informative and knowledgeable about attractions, events etc.

Reviewed on 20 Dec 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,972, price is now NZ$3,868 per person
NZ$3,868
per person
21 Jan - 26 Jan
found 22 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!

Reviewed on 19 Dec 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,112, price is now NZ$2,499 per person
NZ$2,499
per person
21 Jan - 26 Jan
found 22 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Overall good experience. My room was not cleaned one of the nights because the maid didn’t come until late but we were already in our room. Also, the $25/night resort fee was not properly explained to me, didn’t make much sense at all honestly. Property is nice and in a great location but i wouldn’t stay here again

Reviewed on 19 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,198, price is now NZ$2,579 per person
NZ$2,579
per person
21 Jan - 26 Jan
found 22 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.2/10 Wonderful! (326 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on 18 Dec 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was NZ$3,037, price is now NZ$2,511 per person
NZ$2,511
per person
21 Jan - 26 Jan
found 22 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again

Reviewed on 20 Dec 2025

Our guide on 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
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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 of the city at Western Station (Brown Line) or Rockwell Station.

Find hotels in Lincoln Square

Far North Side Holiday

Our pick of the best Far North Side Hotel Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 5 Jan to 6 Jan
NZ$182
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,507 reviews)
Clean Room

Reviewed on 18 Dec 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,130 reviews)
Clean room, attentive staff, great lounge!

Reviewed on 15 Dec 2025

Get rates
Silversmith Hotel Chicago Downtown
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$303 per night from 27 Dec to 28 Dec
NZ$303
27 Dec - 28 Dec
includes taxes & fees
8.4/10 Very Good! (2,134 reviews)
Clean room. I didn’t mind the old door knobs I liked it. Smaller room than anticipated but it was nice and clean.

Reviewed on 14 Dec 2025

Palmer House a Hilton Hotel
See all 5,287 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.

Discover the most popular places to visit in Far North Side

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

What to do in Far North Side

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

NZ$76
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of 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 travellers 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. Travellers 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 travelling 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.