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$180+ Cheap flights from Halifax (YHZ) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in September or January, booked 64 days in advance, depart on a Wednesday or Monday and return on a Monday

Cheap flight deals from Halifax to Chicago

Cheapest flights from Halifax to Chicago
Explore the most affordable flight options available from Halifax to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYHZ - ORD
2 stops15h 24mMultiple Airlines
Tue 1/65:00 amORD - YHZ
1 stop9h 15mMultiple Airlines
Deal found 12/13$405
This Kiwi.com deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:45 amYHZ - ORD
1 stop27h 33mMultiple Airlines
Tue 1/65:00 amORD - YHZ
1 stop9h 15mMultiple Airlines
Deal found 12/13$415
This Kiwi.com deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYHZ - ORD
1 stop12h 02mMultiple Airlines
Mon 1/53:26 pmORD - YHZ
1 stop22h 49mMultiple Airlines
Deal found 12/13$432
This Kiwi.com deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYHZ - ORD
2 stops15h 24mMultiple Airlines
Wed 1/75:29 pmORD - YHZ
1 stop22h 02mMultiple Airlines
Deal found 12/14$433
This Air Canada deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 amYHZ - ORD
2 stops9h 26mAir Canada
Wed 12/313:55 pmORD - YHZ
1 stop6h 31mAir Canada
Deal found 12/13$483
This Air Canada deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 amYHZ - ORD
2 stops9h 26mAir Canada
Thu 1/17:15 amORD - YHZ
1 stop14h 51mAir Canada
Deal found 12/13$522
This Air Canada deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 amYHZ - ORD
2 stops9h 26mAir Canada
Tue 1/68:45 pmORD - YHZ
2 stops12h 19mAir Canada
Deal found 12/13$524
This Air Canada deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:00 amYHZ - ORD
1 stop16h 15mAir Canada
Wed 12/316:00 amORD - YHZ
1 stop6h 31mAir Canada
Deal found 12/13$526
This Air Canada deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:35 amYHZ - ORD
2 stops9h 26mAir Canada
Sun 1/46:00 amORD - YHZ
1 stop15h 54mAir Canada
Deal found 12/13$530
This Kiwi.com deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYHZ - MDW
1 stop14h 58mMultiple Airlines
Fri 1/24:15 pmMDW - YHZ
2 stops18h 20mMultiple Airlines
Deal found 12/13$547
This FlightHub deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/268:25 amYHZ - MDW
2 stops8h 55mPorter Airlines
Mon 12/2911:00 amMDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 12/14$553
This Kiwi.com deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:00 amYHZ - MDW
1 stop14h 58mMultiple Airlines
Thu 1/17:44 amMDW - YHZ
2 stops11h 21mMultiple Airlines
Deal found 12/13$562

Find flight deals from Halifax to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Halifax (YHZ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$238
(Porter Airlines)

One-way from

$180
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$309

Good one-way deal

$371 or less
Provider with most accurate pricing for Halifax Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Halifax Intl-Chicago (CHI) flights.
Search Deals
From Halifax Intl to Chicago (CHI)
Search Deals
One-way flight from Halifax Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a one-way flight from Halifax Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Halifax to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 15, 2025.
Use the filters below to find and compare flights from Halifax to Chicago that are best for you.

Fly from

Halifax

Fly to

Chicago

Route

Depart

Return

Price

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-11:54 pm

2 stops10h 54m

$238

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 2/28

8:30 am-11:55 am

1 stop5h 25m

Chicago Midway

Mon 3/9

11:00 am-8:05 pm

1 stop7h 05m

$326

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 4/2

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Sun 4/5

11:00 am-8:05 pm

1 stop7h 05m

$327

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 1/30

8:45 am-5:52 pm

1 stop11h 07m

Chicago O'Hare Intl

Sun 2/1

7:00 am-10:50 am

2 stops25h 50m

$369

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 1/29

8:30 am-11:46 pm

3 stops17h 16m

Chicago O'Hare Intl

Sun 2/1

8:40 pm-10:50 am

1 stop12h 10m

$373

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 1/30

8:45 am-5:52 pm

1 stop11h 07m

Chicago O'Hare Intl

Sat 1/31

5:32 pm-5:31 pm

2 stops21h 59m

$393

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 1/30

8:45 am-7:52 pm

1 stop13h 07m

Chicago Midway

Sat 1/31

1:26 pm-1:41 am

2 stops10h 15m

$396

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 12/31

9:00 am-7:02 pm

1 stop12h 02m

Chicago O'Hare Intl

Mon 1/5

3:26 pm-4:15 pm

1 stop22h 49m

$432

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 12/31

9:00 am-10:24 pm

2 stops15h 24m

Chicago O'Hare Intl

Wed 1/7

5:29 pm-5:31 pm

1 stop22h 02m

$433

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 1/6

7:00 am-7:02 pm

2 stops14h 02m

Chicago O'Hare Intl

Tue 1/20

5:15 am-1:41 am

2 stops18h 26m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 24 results
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2
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Compare providers for flights from Halifax to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Halifax to Chicago in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Halifax-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Halifax-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Halifax-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Halifax-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Halifax-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Halifax to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Halifax with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Halifax to Chicago

How far ahead should I book a flight from Halifax to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Halifax to Chicago. Price data was last updated on December 12, 2025.

To ensure you get the cheapest price possible for a flight from Halifax to Chicago, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Halifax to Chicago?

Currently, September is the cheapest month in which you can book a flight from Halifax to Chicago (average of $100). Flying from Halifax to Chicago in August is currently the most expensive (average of $441). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 15, 2025.
Read reviews from past customers who have flown United Airlines and Air Canada from Halifax to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
Air Canada
7.1
Good
10,525 reviews
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Halifax to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Halifax to Chicago?

    Halifax Intl (YHZ), located 16.7 mi from the city center, is the airport you fly out of when you book flights from Halifax to Chicago. 1 airline have flights from Halifax Intl to Chicago on a regular basis. Booking flights from Halifax Intl to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • How long is the flight from Halifax to Chicago?

    There are many flights that can get you from Halifax to Chicago in 10h 20m. Fly via Porter Airlines to get the fastest option. Halifax and Chicago are separated by a distance of 1231 mi.

  • What is the cheapest airline to fly from Halifax to Chicago round-trip?

    Flying on Air Canada is currently your cheapest option to Chicago, with prices starting at $119. You may be able to fly from Halifax to Chicago for 68% less than the average price by searching for this airline.

  • What are the most reliable airlines from Halifax to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Halifax to Chicago on time: American Airlines (100%), Envoy Air (100%), SkyWest Airlines (75%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay $371 for a flight from Halifax to Chicago. The cheapest flight overall is $371 while the most popular route, (Halifax Intl - Chicago Midway) is currently priced at $238.

  • Can I find deals for flights from Halifax to Chicago that include hotel bookings?

    Yes. In addition to deals on Halifax to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Halifax to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Halifax to Chicago.

  • Can I find deals for business class flights from Halifax to Chicago?

    Yes. Cheapflights offers flight deals from Halifax to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Halifax to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Halifax to Chicago (average of $100). Flying from Halifax to Chicago in August is currently the most expensive (average of $441). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top airline flying from Halifax to Chicago

Discover the top airline that operate flights from Halifax to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$182Average$474FlexibilityNo cancel feeOn-time67%

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