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$176+ 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in September or December, booked 64 days in advance, depart on a Tuesday or Monday and return on a Wednesday

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 March 23, 2026.

This Mytrip deal was found by Cheapflights users on 3/20. 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.
Wed 9/28:00 am
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Wed 9/911:45 am
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 3/20$312
This Mytrip deal was found by Cheapflights users on 3/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:00 am
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Mon 9/143:20 pm
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 3/19$313
This FlightHub deal was found by Cheapflights users on 3/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Mon 10/53:20 pm
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 3/19$321
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Mon 5/48:00 am
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Mon 5/113:20 pm
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 3/21$360
This Kiwi.com deal was found by Cheapflights users on 3/21. 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.
Sat 4/188:25 am
YHZ
-
MDW
1 stop5h 45m
Porter Airlines
Wed 4/2211:00 am
MDW
-
YHZ
1 stop7h 05m
Porter Airlines
Deal found 3/21$372
This FlightHub deal was found by Cheapflights users on 3/22. 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 6/193:30 pm
YHZ
-
ORD
1 stop7h 01m
WestJet
Mon 6/227:01 am
ORD
-
YHZ
1 stop12h 44m
WestJet
Deal found 3/22$372
This FlightHub deal was found by Cheapflights users on 3/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/183:30 pm
YHZ
-
ORD
1 stop27h 06m
WestJet
Thu 6/258:55 am
ORD
-
YHZ
1 stop10h 50m
WestJet
Deal found 3/19$374
This FlightHub deal was found by Cheapflights users on 3/20. 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.
Wed 7/293:30 pm
YHZ
-
ORD
1 stop5h 11m
WestJet
Mon 8/37:35 pm
ORD
-
YHZ
1 stop24h 10m
WestJet
Deal found 3/20$383
This Mytrip deal was found by Cheapflights users on 3/18. 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.
Fri 4/247:00 am
YHZ
-
MDW
2 stops10h 20m
Porter Airlines
Thu 4/3011:00 am
MDW
-
YHZ
2 stops6h 51m
Porter Airlines
Deal found 3/18$387
This FlightHub deal was found by Cheapflights users on 3/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:30 pm
YHZ
-
ORD
1 stop5h 11m
Multiple Airlines
Mon 10/53:20 pm
ORD
-
YHZ
2 stops6h 24m
Multiple Airlines
Deal found 3/19$394
This FlightHub deal was found by Cheapflights users on 3/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:30 pm
YHZ
-
ORD
1 stop5h 11m
Multiple Airlines
Sun 10/411:45 am
ORD
-
YHZ
2 stops9h 59m
Multiple Airlines
Deal found 3/19$395
This FlightHub deal was found by Cheapflights users on 3/20. 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.
Wed 7/297:00 am
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Mon 8/310:25 am
MDW
-
YHZ
2 stops11h 19m
Porter Airlines
Deal found 3/20$399

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$312
(Mytrip)

One-way from

$176
(Mytrip)

Popular in

January

Cheapest in

September

Average price

$334
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. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 23, 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 7/1

3:30 pm-8:24 pm

1 stop6h 54m

Chicago O'Hare Intl

Sat 7/11

5:45 pm-9:45 pm

1 stop26h 00m

$374

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 4/18

8:25 am-12:10 pm

1 stop5h 45m

Chicago Midway

Wed 4/22

11:00 am-11:54 pm

2 stops10h 54m

$393

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 7/29

8:00 am-2:35 pm

2 stops8h 35m

Chicago Midway

Mon 8/3

3:20 pm-11:44 pm

2 stops6h 24m

$421

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 8/5

8:00 am-2:35 pm

2 stops8h 35m

Chicago Midway

Mon 8/10

3:20 pm-11:44 pm

2 stops6h 24m

$423

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 5/22

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Mon 5/25

3:20 pm-11:44 pm

2 stops6h 24m

$441

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 4/22

11:00 pm-10:15 am

1 stop13h 15m

Chicago Midway

Wed 4/29

11:00 am-12:19 am

1 stop11h 19m

$480

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 5/4

8:00 am-9:40 am

1 stop27h 40m

Chicago Midway

Mon 5/11

3:20 pm-12:24 pm

1 stop19h 04m

$487

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 6/5

3:30 pm-10:29 am

1 stop20h 59m

Chicago O'Hare Intl

Tue 6/9

8:55 am-9:45 pm

1 stop10h 50m

$509

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 7/29

12:55 pm-7:40 pm

1 stop8h 45m

Chicago O'Hare Intl

Mon 8/3

7:35 pm-9:45 pm

1 stop24h 10m

$512

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 8/4

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Mon 8/10

3:20 pm-11:44 pm

2 stops6h 24m

$518

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 39 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 March.
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

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 March 13, 2026.

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 $98). Flying from Halifax to Chicago in March is currently the most expensive (average of $563). 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 March 23, 2026.
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
9,462 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,462 reviews
United Airlines
7.4
Good
9,462 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
Air Canada
7.1
Good
10,835 reviews
United Airlines
7.4
Good
9,462 reviews

Boarding

7.7

Entertainment

7.1

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 01m. Fly via Porter Airlines or WestJet 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 58% less than the average price by searching for this airline.

  • 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 $98). Flying from Halifax to Chicago in March is currently the most expensive (average of $563). 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

Browse thousands of different options on Cheapflights for your next trip

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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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$182Average$481FlexibilityNo cancel feeOn-time67%

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