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Cheap flights from Halifax to Chicago from C$ 254

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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
18 Jul — 25 Jul1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in September or December, booked 66 days in advance, depart on a Monday or Friday and return on a Monday

Cheap flight deals from Halifax to Chicago

Enter your travel dates to find the best prices.

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 18 June 2026.

Thu 17/97:00 a.m.
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Wed 23/93:20 p.m.
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 14/6C$ 469
Fri 25/97:00 a.m.
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Tue 29/97:00 a.m.
ORD
-
YHZ
2 stops7h 29m
Porter Airlines
Deal found 15/6C$ 480
Wed 19/82:30 p.m.
YHZ
-
ORD
1 stop7h 35m
Air Canada
Tue 22/93:40 p.m.
ORD
-
YHZ
1 stop6h 15m
Air Canada
Deal found 15/6C$ 481
Tue 14/75:15 a.m.
YHZ
-
ORD
1 stop5h 45m
Air Canada
Tue 21/78:45 a.m.
ORD
-
YHZ
1 stop7h 31m
Air Canada
Deal found 13/6C$ 487
Wed 15/78:00 a.m.
YHZ
-
MDW
2 stops27h 40m
Porter Airlines
Thu 16/73:20 p.m.
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 13/6C$ 488
Thu 17/97:00 a.m.
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Sun 20/93:20 p.m.
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 14/6C$ 490
Mon 13/77:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Wed 22/710:25 a.m.
MDW
-
YHZ
2 stops11h 19m
Porter Airlines
Deal found 16/6C$ 492
Thu 17/96:20 a.m.
YHZ
-
ORD
1 stop10h 15m
Multiple Airlines
Sun 20/911:45 a.m.
ORD
-
YHZ
1 stop21h 00m
Multiple Airlines
Deal found 14/6C$ 499
Thu 20/88:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Wed 26/810:20 a.m.
MDW
-
YHZ
2 stops11h 24m
Porter Airlines
Deal found 17/6C$ 502
Wed 23/92:50 p.m.
YHZ
-
ORD
1 stop11h 38m
United Airlines
Sat 26/94:00 p.m.
ORD
-
YHZ
1 stop5h 55m
United Airlines
Deal found 17/6C$ 511
Tue 25/88:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Sat 29/810:20 a.m.
MDW
-
YHZ
2 stops11h 24m
Porter Airlines
Deal found 16/6C$ 513
Tue 25/86:25 a.m.
YHZ
-
ORD
1 stop5h 51m
Air Canada
Sat 29/88:45 a.m.
ORD
-
YHZ
1 stop7h 31m
Air Canada
Deal found 17/6C$ 513

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 18 June 2026.

Round-trip from

C$ 469

One-way from

C$ 254

Popular in

January

Cheapest in

September

Average price

C$ 627

Good round-trip deal

C$ 590 or less

Good one-way deal

C$ 383 or less
Porter Airlines
  • Porter Airlines
  • 17/9-23/9
  • 4 total stops
  • 15h 59m total
  • Halifax to Chicago
Search Deals
9/9
  • 9/9
  • 1 total stop
  • 16h 45m total
  • Halifax to Chicago
Search Deals
High demand for flights, 1% potential price rise
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 629,999 searches. Data last updated 18 June 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

Sat 26/9

7:00 a.m.-2:35 p.m.

2 stops9h 35m

Chicago O'Hare Intl

Tue 29/9

11:45 a.m.-11:44 p.m.

2 stops9h 59m

C$ 480

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 20/8

7:00 a.m.-2:35 p.m.

2 stops9h 35m

Chicago Midway

Wed 26/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 501

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 26/9

7:00 a.m.-9:32 p.m.

1 stop16h 32m

Chicago O'Hare Intl

Tue 29/9

4:00 p.m.-11:55 p.m.

1 stop5h 55m

C$ 512

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 23/9

2:50 p.m.-12:28 a.m.

1 stop11h 38m

Chicago O'Hare Intl

Sat 26/9

4:00 p.m.-11:55 p.m.

1 stop5h 55m

C$ 512

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 23/9

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Sat 26/9

11:45 a.m.-11:44 p.m.

2 stops9h 59m

C$ 515

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 13/7

8:15 p.m.-9:40 a.m.

1 stop15h 25m

Chicago Midway

Wed 22/7

10:25 a.m.-9:25 p.m.

1 stop9h 00m

C$ 533

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 29/6

1:27 p.m.-7:11 p.m.

1 stop7h 44m

Chicago O'Hare Intl

Sat 4/7

8:30 a.m.-3:57 p.m.

1 stop5h 27m

C$ 533

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 15/7

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Thu 16/7

10:25 a.m.-11:44 p.m.

2 stops11h 19m

C$ 567

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 25/8

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Sat 29/8

10:20 a.m.-11:44 p.m.

2 stops11h 24m

C$ 568

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 4/7

4:50 p.m.-6:43 p.m.

Nonstop3h 53m

Chicago O'Hare Intl

Tue 7/7

2:25 p.m.-11:55 p.m.

1 stop7h 30m

C$ 579

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/6

Showing 1-10 of 31 resultsSorted by cheapest first
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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 C$ 88). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 672). 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 18 June 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 18 June 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?

What’s the top layover airport for flights from Halifax to Chicago?

Share of one-stop round-trip flights from Halifax to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Montreal (YUL) – chosen by Cheapflights users on 45% of one-stop itineraries from Halifax to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Halifax to Chicago?

Average round-trip fare for 1-stop flights from Halifax to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of C$ 290.

What’s the fastest layover option from Halifax to Chicago?

Shortest average travel time for 1-stop one-way flights from Halifax to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Detroit (DTW) have the shortest average one-way travel time for 1-stop routes: 5h 07m.

Which airport typically offers the quickest layover for flights from Halifax to Chicago?

Average layover duration for 1-stop one-way flights from Halifax to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Detroit (DTW) offer the fastest connection on this route, with an average layover time of 1h 27m.

How far ahead should I book a flight from Halifax to Chicago?

To ensure you get the cheapest price possible for a flight from Halifax to Chicago, you should look to book at least 42 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.

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 18 June 2026.
Read through reviews of airlines operating flights from Halifax to Chicago, such as Porter Airlines,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
438 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
United Airlines
7.4
Good
9,857 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
WestJet
7.2
Good
3,373 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Air Canada
7.1
Good
11,210 reviews
Porter Airlines
8.0
Very good
438 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.6

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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?

    For a flight from Halifax to Chicago, you will be flying from Halifax Intl. Halifax Intl (YHZ) is just 26.9 km from the centre of the city. Halifax Intl is the only Halifax airport and it handles 2 outbound flights to Chicago per day. 3 airlines have flights to Chicago from Halifax Intl on a regular basis.

  • How long is the flight from Halifax to Chicago?

    For as low as C$ 480, Porter Airlines can have you in Chicago from Halifax in 9h 35m. The distance from Halifax to Chicago is about 1988 km. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Halifax to Chicago round-trip?

    United Airlines, at C$ 229, was found to be the cheapest airline from Halifax to Chicago.Alternate airlines to your destination round-trip include Air Canada and Porter Airlines. Users have found that United Airlines is 63% cheaper than the other options available to this destination.

  • 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 C$ 792 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 307 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 469.

  • 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 C$ 88). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 672). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Halifax to Chicago

Discover the top 3 airlines 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 629,999 searches. Data last updated 18 June 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 229AverageC$ 229FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 290AverageC$ 692FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 474AverageC$ 661FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Halifax to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Halifax to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Halifax to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Halifax.

Can Cheapflights find flights from Halifax to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Halifax? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Halifax to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Halifax to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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