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$177+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Jul 24 — Jul 311
Fri 7/24
Fri 7/31
1 adult, Economy
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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 June 24, 2026.

This oojo deal was found by Cheapflights users on 6/19. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 pm
YHZ
-
MDW
2 stops17h 40m
Porter Airlines
Fri 8/283:15 pm
MDW
-
YHZ
2 stops6h 29m
Porter Airlines
Deal found 6/19$310
This Trip.com deal was found by Cheapflights users on 6/21. 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.
Wed 8/56:25 am
YHZ
-
ORD
1 stop5h 51m
Air Canada
Wed 8/128:40 am
ORD
-
YHZ
1 stop5h 27m
Air Canada
Deal found 6/21$317
This oojo deal was found by Cheapflights users on 6/21. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:00 am
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Tue 7/283:20 pm
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 6/21$323
This Booking.com deal was found by Cheapflights users on 6/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:00 am
YHZ
-
MDW
2 stops8h 35m
Porter Airlines
Tue 8/253:15 pm
MDW
-
YHZ
2 stops6h 29m
Porter Airlines
Deal found 6/23$336
This United Airlines deal was found by Cheapflights users on 6/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:00 am
YHZ
-
ORD
1 stop5h 58m
United Airlines
Wed 9/231:30 pm
ORD
-
YHZ
1 stop8h 25m
United Airlines
Deal found 6/21$341
This Air Canada deal was found by Cheapflights users on 6/23. 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 8/119:00 am
YHZ
-
ORD
1 stop6h 22m
Air Canada
Tue 8/2511:05 am
ORD
-
YHZ
1 stop5h 11m
Air Canada
Deal found 6/23$342
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 9/178:00 am
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Tue 9/293:20 pm
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 6/21$343
This Justfly.com deal was found by Cheapflights users on 6/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:00 am
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Sat 9/511:45 am
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 6/24$346
This Air Canada deal was found by Cheapflights users on 6/23. 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 8/46:25 am
YHZ
-
ORD
2 stops8h 54m
Air Canada
Wed 8/127:25 am
ORD
-
YHZ
2 stops9h 40m
Air Canada
Deal found 6/23$347
This Air Canada deal was found by Cheapflights users on 6/21. 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 10/65:45 am
YHZ
-
ORD
1 stop6h 32m
Air Canada
Wed 10/78:45 am
ORD
-
YHZ
1 stop5h 17m
Air Canada
Deal found 6/21$348
This Porter Airlines deal was found by Cheapflights users on 6/21. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:40 pm
YHZ
-
ORD
2 stops9h 55m
Porter Airlines
Wed 10/73:20 pm
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 6/21$349
This Justfly.com deal was found by Cheapflights users on 6/23. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:00 am
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Tue 10/63:20 pm
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 6/23$350

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 June 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$310
(oojo)

One-way from

$177
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$447

Good one-way deal

$260 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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 24, 2026.
Use the filters below to find and compare flights from Halifax to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 9/2

8:00 am-2:35 pm

1 stop8h 35m

Chicago O'Hare Intl

Sat 9/5

11:45 am-11:44 pm

2 stops9h 59m

$346

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 7/13

4:50 pm-6:43 pm

Nonstop3h 53m

Chicago O'Hare Intl

Wed 7/22

6:00 am-11:55 pm

1 stop15h 55m

$356

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 8/11

8:00 am-2:35 pm

2 stops8h 35m

Chicago Midway

Tue 8/25

3:15 pm-11:44 pm

2 stops6h 29m

$356

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 8/25

6:25 am-10:16 am

1 stop5h 51m

Chicago O'Hare Intl

Sat 8/29

8:40 am-6:16 pm

1 stop7h 36m

$363

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 9/13

7:25 am-2:35 pm

2 stops9h 10m

Chicago O'Hare Intl

Mon 9/14

11:45 am-11:44 pm

2 stops9h 59m

$380

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 10/15

7:00 am-2:35 pm

2 stops9h 35m

Chicago O'Hare Intl

Sun 10/18

3:20 pm-10:45 am

1 stop17h 25m

$389

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 7/13

8:00 am-2:35 pm

2 stops8h 35m

Chicago Midway

Wed 7/22

10:25 am-11:44 pm

2 stops11h 19m

$389

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 8/25

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Sat 8/29

10:20 am-11:44 pm

2 stops11h 24m

$401
Quickest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 8/11

3:30 pm-6:33 pm

1 stop5h 03m

Chicago Midway

Tue 8/25

1:25 pm-9:10 pm

1 stop5h 45m

$406

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 8/11

12:05 pm-11:22 pm

2 stops13h 17m

Chicago O'Hare Intl

Tue 8/25

6:00 am-4:01 pm

1 stop8h 01m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/24

Showing 1-10 of 32 resultsSorted by cheapest first
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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 June.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Halifax-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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 $63). Flying from Halifax to Chicago in January is currently the most expensive (average of $479). 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 June 24, 2026.

When flying from Halifax to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Halifax to Chicago

Explore weekly flight availability from Halifax to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 24, 2026.

The most flights from YHZ to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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

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 2 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 3h 53m. Fly via Porter Airlines, United Airlines, or Air Canada 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 59% 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: SkyWest Airlines (85%), Air Canada (85%), United Airlines (85%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay $295 for a flight from Halifax to Chicago. The cheapest flight overall is $228 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at $353.

  • 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 $63). Flying from Halifax to Chicago in January is currently the most expensive (average of $479). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Halifax to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Halifax to St. Louis flights

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 June 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$182Average$479FlexibilityNo cancel feeOn-time67%

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