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$178+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
May 18 — May 251
Mon 5/18
Mon 5/25
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 Wednesday or Monday and return on a Saturday

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 April 18, 2026.

This Trip.com deal was found by Cheapflights users on 4/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:00 am
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Wed 10/147:00 am
ORD
-
YHZ
2 stops7h 24m
Porter Airlines
Deal found 4/14$315
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/217:00 am
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Wed 5/2710:30 am
MDW
-
YHZ
2 stops11h 17m
Porter Airlines
Deal found 4/16$319
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:00 am
YHZ
-
ORD
2 stops8h 35m
Porter Airlines
Wed 9/911:45 am
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 4/13$339
This FlightHub deal was found by Cheapflights users on 4/16. 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.
Sun 10/41:40 pm
YHZ
-
ORD
2 stops9h 55m
Porter Airlines
Thu 10/811:45 am
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 4/16$341
This Kiwi.com deal was found by Cheapflights users on 4/13. 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.
Thu 5/218:15 pm
YHZ
-
MDW
1 stop15h 30m
Multiple Airlines
Wed 5/2710:30 am
MDW
-
YHZ
2 stops11h 17m
Multiple Airlines
Deal found 4/13$347
This FlightHub deal was found by Cheapflights users on 4/16. 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 9/47:00 am
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Tue 9/811:45 am
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 4/16$349
This Mytrip deal was found by Cheapflights users on 4/16. 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 5/2111:45 am
YHZ
-
ORD
1 stop9h 55m
Multiple Airlines
Wed 5/279:55 am
ORD
-
YHZ
2 stops11h 52m
Multiple Airlines
Deal found 4/16$355
This Porter Airlines deal was found by Cheapflights users on 4/14. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:40 pm
YHZ
-
ORD
2 stops9h 55m
Porter Airlines
Sat 9/197:00 am
ORD
-
YHZ
2 stops7h 24m
Porter Airlines
Deal found 4/14$361
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Mon 5/411:00 pm
YHZ
-
MDW
1 stop12h 45m
Multiple Airlines
Fri 5/810:30 am
MDW
-
YHZ
1 stop8h 55m
Multiple Airlines
Deal found 4/14$367
This FlightHub deal was found by Cheapflights users on 4/15. 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 5/137:00 am
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Wed 5/2010:30 am
MDW
-
YHZ
2 stops11h 17m
Porter Airlines
Deal found 4/15$368
This eDestinos deal was found by Cheapflights users on 4/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/143:30 pm
YHZ
-
ORD
1 stop26h 56m
WestJet
Tue 6/1611:30 am
ORD
-
YHZ
1 stop8h 15m
WestJet
Deal found 4/13$379

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 April 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$315
(Trip.com)

One-way from

$178
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$479

Good round-trip deal

$213 or less

Good one-way deal

$205 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 April 2026
Search Deals
Price to beat on a round-trip flight from Halifax Intl to Chicago (CHI).
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 April 18, 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 - MDW

YHZMDW

Halifax Intl

Thu 5/21

7:00 am-2:35 pm

2 stops9h 35m

Chicago Midway

Wed 5/27

3:20 pm-11:47 pm

2 stops6h 27m

$354

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 9/18

8:00 am-2:35 pm

1 stop8h 35m

Chicago O'Hare Intl

Sat 9/19

7:00 am-4:24 pm

2 stops7h 24m

$361

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 6/14

3:30 pm-4:26 pm

1 stop26h 56m

Chicago O'Hare Intl

Tue 6/16

11:30 am-9:45 pm

1 stop8h 15m

$379

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 7/8

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Wed 7/22

6:00 am-9:40 pm

2 stops13h 40m

$431

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 6/17

7:00 am-2:35 pm

2 stops9h 35m

Chicago Midway

Wed 6/24

3:20 pm-11:44 pm

2 stops6h 24m

$438

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 7/8

8:00 am-2:35 pm

2 stops8h 35m

Chicago Midway

Wed 7/22

10:25 am-11:44 pm

2 stops11h 19m

$464

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 5/31

8:00 am-9:40 am

1 stop27h 40m

Chicago Midway

Sun 6/7

6:00 am-9:45 pm

2 stops13h 45m

$471

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 8/25

7:00 am-2:35 pm

2 stops9h 35m

Chicago Midway

Sat 8/29

10:25 am-11:44 pm

2 stops11h 19m

$474
Quickest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 6/18

8:00 am-2:35 pm

2 stops8h 35m

Chicago Midway

Thu 6/25

3:20 pm-11:44 pm

2 stops6h 24m

$474

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 6/18

8:30 am-6:29 pm

2 stops11h 59m

Chicago O'Hare Intl

Thu 6/25

7:17 pm-9:40 pm

1 stop24h 23m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 34 resultsSorted by cheapest first
1
2
3
4

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 April.
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 April 10, 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 $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.

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 April 18, 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
9,605 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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
9,605 reviews
United Airlines
7.4
Good
9,605 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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
10,935 reviews
United Airlines
7.4
Good
9,605 reviews

Overall

7.4

Comfort

7.3

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.6

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 9h 35m. Fly via Porter Airlines or WestJet to get the fastest option. Halifax and Chicago are separated by a distance of 1231 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 cheapest flights from Halifax to Chicago?

    On average you can expect to pay $425 for a flight from Halifax to Chicago. The cheapest flight overall is $153 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at $315.

  • 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

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 April 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$182Average$506FlexibilityNo cancel feeOn-time67%

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