HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$157+ 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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Halifax to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 5, 2026.

This FlightHub deal was found by Cheapflights users on 2/5. 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 9/107:00 am
YHZ
-
MDW
2 stops11h 50m
Porter Airlines
Sun 9/1310:25 am
MDW
-
YHZ
2 stops11h 09m
Porter Airlines
Deal found 2/5$268
This Porter Airlines deal was found by Cheapflights users on 2/5. 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.
Sat 2/288:30 am
YHZ
-
MDW
1 stop5h 25m
Porter Airlines
Thu 3/511:00 am
MDW
-
YHZ
2 stops8h 27m
Porter Airlines
Deal found 2/5$294
This Porter Airlines deal was found by Cheapflights users on 2/3. 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.
Mon 4/207:00 am
YHZ
-
MDW
2 stops10h 20m
Porter Airlines
Tue 4/2111:00 am
MDW
-
YHZ
1 stop7h 05m
Porter Airlines
Deal found 2/3$315
This FlightHub deal was found by Cheapflights users on 2/4. 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 stop6h 54m
WestJet
Mon 6/227:35 pm
ORD
-
YHZ
1 stop24h 05m
WestJet
Deal found 2/4$327
This FlightHub deal was found by Cheapflights users on 2/4. 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 8/56:15 pm
YHZ
-
ORD
2 stops17h 49m
WestJet
Wed 8/191:15 pm
ORD
-
YHZ
2 stops30h 00m
WestJet
Deal found 2/4$329
This Justfly.com deal was found by Cheapflights users on 2/5. 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 9/116:15 pm
YHZ
-
ORD
2 stops19h 53m
WestJet
Mon 9/1410:35 am
ORD
-
YHZ
1 stop9h 05m
WestJet
Deal found 2/5$332
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/258:20 pm
YHZ
-
MDW
1 stop15h 50m
Multiple Airlines
Wed 3/411:00 am
MDW
-
YHZ
1 stop8h 55m
Multiple Airlines
Deal found 2/5$334
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/198:20 pm
YHZ
-
ORD
2 stops29h 27m
Multiple Airlines
Wed 2/258:30 am
ORD
-
YHZ
1 stop31h 01m
Multiple Airlines
Deal found 2/3$347
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 3/56:40 pm
YHZ
-
MDW
1 stop17h 25m
Porter Airlines
Thu 3/1211:00 am
MDW
-
YHZ
1 stop7h 05m
Porter Airlines
Deal found 2/5$348
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/258:20 pm
YHZ
-
MDW
1 stop15h 50m
Multiple Airlines
Thu 3/511:00 am
MDW
-
YHZ
1 stop7h 05m
Multiple Airlines
Deal found 2/5$351
This WestJet deal was found by Cheapflights users on 2/5. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:15 pm
YHZ
-
ORD
2 stops17h 49m
WestJet
Sun 9/138:55 am
ORD
-
YHZ
2 stops8h 20m
WestJet
Deal found 2/5$354
This FlightHub deal was found by Cheapflights users on 2/3. 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 6/188:15 pm
YHZ
-
ORD
2 stops24h 26m
WestJet
Thu 6/257:35 pm
ORD
-
YHZ
1 stop24h 05m
WestJet
Deal found 2/3$371

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$294
(Porter Airlines)

One-way from

$157
(FlightHub)

Popular in

January

Cheapest in

September

Average price

$301

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. 4% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 February 5, 2026.
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

Sat 2/28

8:30 am-11:55 am

1 stop5h 25m

Chicago Midway

Thu 3/5

11:00 am-9:27 pm

2 stops8h 27m

$294

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 2/28

8:30 am-11:55 am

1 stop5h 25m

Chicago Midway

Wed 3/4

11:00 am-11:54 pm

2 stops10h 54m

$294

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 4/20

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Tue 4/21

11:00 am-11:54 pm

2 stops10h 54m

$315

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 6/19

6:15 pm-7:48 pm

2 stops27h 33m

Chicago O'Hare Intl

Mon 6/22

7:35 pm-9:40 pm

1 stop24h 05m

$331

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 3/5

6:40 pm-10:05 am

1 stop17h 25m

Chicago Midway

Thu 3/12

11:00 am-8:05 pm

1 stop7h 05m

$348

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 2/19

8:20 pm-9:13 pm

2 stops26h 53m

Chicago O'Hare Intl

Wed 2/25

8:30 am-5:31 pm

1 stop31h 01m

$367

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 6/18

8:15 pm-6:41 pm

2 stops24h 26m

Chicago O'Hare Intl

Thu 6/25

7:35 pm-9:40 pm

1 stop24h 05m

$371

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 3/17

1:20 pm-10:36 am

2 stops23h 16m

Chicago O'Hare Intl

Tue 3/24

6:36 pm-4:15 pm

1 stop19h 39m

$388

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 3/21

6:00 am-1:01 pm

1 stop9h 01m

Chicago O'Hare Intl

Sat 3/28

3:55 pm-1:41 am

1 stop7h 46m

$401

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 5/10

6:20 am-12:43 pm

1 stop8h 23m

Chicago O'Hare Intl

Mon 5/11

5:30 pm-8:10 am

1 stop12h 40m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 26 results
1
2
3

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 February.
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 January 30, 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 $100). 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 February 5, 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
9,240 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

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
9,240 reviews
United Airlines
7.4
Good
9,240 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

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
10,694 reviews
United Airlines
7.4
Good
9,240 reviews

Entertainment

7.1

Crew

8.1

Food

6.6

Overall

7.4

Boarding

7.7

Comfort

7.3

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 5h 25m. 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 54% 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 $371 for a flight from Halifax to Chicago. The cheapest flight overall is $371 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at $356.

  • 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 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$182Average$480FlexibilityNo cancel feeOn-time67%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.