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$109+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 51 days in advance, depart on a Saturday or Tuesday and return on a Monday

Find 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 October 30, 2025.

This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:35 amYHZ - ORD
1 stop7h 43mAir Canada
Wed 11/262:00 pmORD - YHZ
1 stop6h 06mAir Canada
Deal found 10/29$166
This Air Canada deal was found by Cheapflights users on 10/30. 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 12/26:55 amYHZ - ORD
1 stop6h 23mAir Canada
Tue 12/910:00 amORD - YHZ
1 stop5h 41mAir Canada
Deal found 10/30$182
This Air Canada deal was found by Cheapflights users on 10/30. 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 11/116:55 amYHZ - ORD
1 stop6h 23mAir Canada
Tue 11/118:15 pmORD - YHZ
1 stop11h 10mAir Canada
Deal found 10/30$206
This Air Canada deal was found by Cheapflights users on 10/30. 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 11/116:55 amYHZ - ORD
1 stop6h 23mAir Canada
Thu 11/1312:50 pmORD - YHZ
1 stop9h 16mAir Canada
Deal found 10/30$209
This Air Canada deal was found by Cheapflights users on 10/30. 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 11/127:00 amYHZ - ORD
1 stop8h 01mAir Canada
Fri 11/148:15 pmORD - YHZ
1 stop11h 10mAir Canada
Deal found 10/30$212
This Air Canada deal was found by Cheapflights users on 10/30. 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 11/127:00 amYHZ - ORD
1 stop8h 01mAir Canada
Thu 11/1312:50 pmORD - YHZ
1 stop9h 16mAir Canada
Deal found 10/30$215
This Air Canada deal was found by Cheapflights users on 10/30. 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 11/116:55 amYHZ - ORD
2 stops10h 15mAir Canada
Fri 11/148:15 pmORD - YHZ
1 stop11h 10mAir Canada
Deal found 10/30$217
This Air Canada deal was found by Cheapflights users on 10/29. 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.
Thu 12/255:35 amYHZ - ORD
1 stop7h 43mAir Canada
Thu 1/112:50 pmORD - YHZ
1 stop9h 16mAir Canada
Deal found 10/29$240
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/206:00 amYHZ - MDW
1 stop11h 20mMultiple Airlines
Wed 11/2611:00 amMDW - YHZ
1 stop7h 10mMultiple Airlines
Deal found 10/29$382
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/207:00 amYHZ - MDW
2 stops10h 20mPorter Airlines
Wed 11/2611:00 amMDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 10/29$396
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:25 amYHZ - MDW
1 stop8h 55mMultiple Airlines
Mon 12/19:41 amMDW - YHZ
2 stops23h 09mMultiple Airlines
Deal found 10/28$406
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/28:25 amYHZ - MDW
1 stop27h 40mPorter Airlines
Tue 12/911:00 amMDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 10/30$419

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$166
(Trip.com)

One-way from

$109
(Mytrip)

Popular in

July

Cheapest in

September

Average price

$431
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. 23% potential increase in price ($113 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 30, 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 - ORD

YHZORD

Halifax Intl

Thu 11/20

5:35 am-11:18 am

1 stop7h 43m

Chicago O'Hare Intl

Wed 11/26

2:00 pm-10:06 pm

1 stop6h 06m

$166

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 12/2

6:55 am-11:18 am

1 stop6h 23m

Chicago O'Hare Intl

Tue 12/9

2:00 pm-10:26 pm

1 stop6h 26m

$182

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 3/24

6:55 am-1:01 pm

2 stops8h 06m

Chicago O'Hare Intl

Wed 3/25

7:15 am-3:47 pm

1 stop6h 32m

$202

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 11/11

6:55 am-11:18 am

1 stop6h 23m

Chicago O'Hare Intl

Tue 11/11

8:15 pm-9:25 am

1 stop11h 10m

$206

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 11/11

6:55 am-11:18 am

1 stop6h 23m

Chicago O'Hare Intl

Fri 11/14

8:15 pm-9:25 am

1 stop11h 10m

$206

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 11/11

6:55 am-11:18 am

1 stop6h 23m

Chicago O'Hare Intl

Wed 11/12

10:00 am-12:26 am

1 stop12h 26m

$206

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 11/12

7:00 am-1:01 pm

1 stop8h 01m

Chicago O'Hare Intl

Thu 11/13

12:50 pm-12:06 am

1 stop9h 16m

$215

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 11/13

5:35 am-1:01 pm

2 stops9h 26m

Chicago O'Hare Intl

Fri 11/14

8:15 pm-9:25 am

1 stop11h 10m

$217

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 12/25

5:35 am-11:18 am

1 stop7h 43m

Chicago O'Hare Intl

Thu 1/1

12:50 pm-12:06 am

1 stop9h 16m

$240

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 11/13

5:35 am-11:18 am

1 stop7h 43m

Chicago O'Hare Intl

Mon 11/17

8:15 pm-11:04 am

2 stops12h 49m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 34 results
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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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 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 October 24, 2025.

To ensure you get the cheapest price possible for a flight from Halifax to Chicago, you should look to book at least 50 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.

What is the cheapest time of day to fly from YHZ to CHI?

Find hourly flight availability from Halifax to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

One of the essential ways to save on airfare from Halifax to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 56% on airfare.

How much does it cost to fly round-trip from Halifax to Chicago?

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 October 30, 2025.
Read reviews from past customers who have flown 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.
Air Canada
7.1
Good
10,381 reviews

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Crew

7.8

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2024

YVR - LAX

Seamless in all ways..arriving 25 minutes early into Los Angeles was outstanding
Air Canada
7.1
Good
10,381 reviews
Air Canada
7.1
Good
10,381 reviews

Comfort

7.1

Entertainment

6.8

Food

6.3

Overall

7.1

Crew

7.8

Boarding

7.3

Reviews

1 / 20
10.0
Excellent

Anonymous,Jul 2024

YVR - LAX

Seamless in all ways..arriving 25 minutes early into Los Angeles was outstanding

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 7h 43m. Fly via Air Canada, Delta, or Porter Airlines to get the fastest option. Halifax and Chicago are separated by a distance of 1235 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $182. You may be able to fly from Halifax to Chicago for 50% less than the average price by searching for this airline.

  • What are the cheapest airlines to fly from Halifax to Chicago one-way?

    One-way options have recently been found by users for as low as $109 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from $112 and Delta from $235 one-way.

  • 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 (90%), Envoy Air (90%), SkyWest Airlines (67%).

  • 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$182Average$474FlexibilityNo cancel feeOn-time67%

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