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Cheap flights from Halifax to Chicago from C$ 243

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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
5 Aug — 12 Aug1
1 adult
1 adult, Economy, 0 bags

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 6 July 2026.

Mon 12/108:00 a.m.
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Fri 23/103:20 p.m.
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 2/7C$ 419
Fri 25/98:00 a.m.
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Tue 6/1011:45 a.m.
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 2/7C$ 422
Fri 24/78:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Sun 26/73:20 p.m.
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 1/7C$ 429
Tue 1/98:00 a.m.
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
Tue 8/911:45 a.m.
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 2/7C$ 429
Thu 30/77:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Thu 6/810:25 a.m.
MDW
-
YHZ
2 stops11h 19m
Porter Airlines
Deal found 1/7C$ 449
Wed 12/88:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Wed 26/810:25 a.m.
MDW
-
YHZ
2 stops11h 19m
Porter Airlines
Deal found 2/7C$ 450
Fri 31/78:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Fri 7/83:15 p.m.
MDW
-
YHZ
2 stops6h 29m
Porter Airlines
Deal found 2/7C$ 454
Wed 12/86:25 a.m.
YHZ
-
ORD
1 stop5h 51m
Air Canada
Wed 26/88:40 a.m.
ORD
-
YHZ
1 stop5h 27m
Air Canada
Deal found 2/7C$ 456
Fri 25/96:25 a.m.
YHZ
-
ORD
1 stop5h 52m
Air Canada
Tue 6/108:45 a.m.
ORD
-
YHZ
1 stop5h 17m
Air Canada
Deal found 2/7C$ 457
Mon 20/74:50 p.m.
YHZ
-
ORD
Nonstop3h 53m
United Airlines
Thu 6/86:00 a.m.
ORD
-
YHZ
1 stop15h 55m
United Airlines
Deal found 2/7C$ 463
Wed 2/96:25 a.m.
YHZ
-
ORD
1 stop5h 51m
Air Canada
Sun 6/98:40 a.m.
ORD
-
YHZ
1 stop5h 27m
Air Canada
Deal found 1/7C$ 464
Fri 23/105:15 a.m.
YHZ
-
ORD
1 stop5h 45m
Air Canada
Fri 23/105:35 p.m.
ORD
-
YHZ
1 stop6h 19m
Air Canada
Deal found 2/7C$ 470

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 6 July 2026.

Round-trip from

C$ 419

One-way from

C$ 243

Popular in

January

Cheapest in

September

Average price

C$ 701

Good round-trip deal

C$ 703 or less

Good one-way deal

C$ 311 or less
Porter Airlines
  • Porter Airlines
  • 12/10-23/10
  • 3 total stops
  • 14h 59m total
  • Halifax to Chicago
Search Deals
United Airlines
  • United Airlines
  • 5/9
  • Nonstop
  • 3h 45m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 6 July 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

Fri 24/7

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

2 stops8h 35m

Chicago Midway

Sun 26/7

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 461

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$ 507

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 25/8

6:25 a.m.-10:16 a.m.

1 stop5h 51m

Chicago O'Hare Intl

Sat 29/8

2:35 p.m.-11:55 p.m.

1 stop7h 20m

C$ 520

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 2/9

6:30 a.m.-4:59 p.m.

2 stops12h 29m

Chicago Midway

Sun 6/9

9:24 a.m.-9:10 p.m.

1 stop9h 46m

C$ 548

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 2/9

6:30 a.m.-4:17 p.m.

2 stops11h 47m

Chicago O'Hare Intl

Sun 6/9

11:22 a.m.-9:10 p.m.

1 stop7h 48m

C$ 548

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 24/7

5:05 p.m.-10:05 p.m.

1 stop7h 00m

Chicago O'Hare Intl

Sun 26/7

8:45 a.m.-4:07 p.m.

1 stop5h 22m

C$ 552

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 25/8

3:30 p.m.-6:33 p.m.

1 stop5h 03m

Chicago Midway

Sat 29/8

9:24 a.m.-9:10 p.m.

1 stop9h 46m

C$ 554
Quickest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 30/7

3:30 p.m.-8:31 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Thu 6/8

1:59 p.m.-9:10 p.m.

1 stop5h 11m

C$ 554

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 24/7

6:10 p.m.-8:28 a.m.

2 stops16h 18m

Chicago O'Hare Intl

Sun 26/7

4:37 p.m.-1:54 a.m.

1 stop7h 17m

C$ 576

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 21/7

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

1 stop8h 35m

Chicago Midway

Fri 24/7

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 596

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 29 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$ 89). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 680). 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 6 July 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 6 July 2026.

The most flights from YHZ to CHI are scheduled on a Saturday (4 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.

Detroit (DTW) is the most affordable 1-stop option, with an average round-trip price of C$ 505.

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.

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 6 July 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
7.9
Good
442 reviews
Check prices

Overall

7.9

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

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
7.9
Good
442 reviews
Porter Airlines
7.9
Good
442 reviews
Check prices

Overall

7.9

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

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
9,945 reviews
Porter Airlines
7.9
Good
442 reviews
Check prices

Overall

7.9

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

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
3,398 reviews
Porter Airlines
7.9
Good
442 reviews
Check prices

Overall

7.9

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

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
11,313 reviews
Porter Airlines
7.9
Good
442 reviews
Check prices

Overall

7.9

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

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. 2 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$ 461, Porter Airlines can have you in Chicago from Halifax in 8h 35m. The distance from Halifax to Chicago is about 1981 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$ 232, was found to be the cheapest airline from Halifax to Chicago. An alternate airline flying to your destination would be Air Canada. Users have found that United Airlines is 61% 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: American Airlines (100%), Qatar Airways (100%), Envoy Air (100%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 696 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 244 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 419.

  • 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$ 89). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 680). 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 2 airlines flying from Halifax to Chicago

Discover the top 2 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 6 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 232AverageC$ 232FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 294AverageC$ 606FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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