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Cheap flights from Halifax to Chicago from C$ 266

YHZ — CHI
30 Sep — 7 Oct1
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

Fri 25/96:25 a.m. -
1 stop5h 50m
Mon 5/105:35 p.m. -
1 stop6h 19m
Deal found 26/8C$ 497
Sun 11/106:25 a.m. -
1 stop5h 52m
Sun 18/108:45 a.m. -
1 stop5h 17m
Deal found 27/8C$ 513
Fri 13/116:05 a.m. -
1 stop7h 02m
Mon 16/1112:50 p.m. -
1 stop7h 48m
Deal found 27/8C$ 520
Tue 1/125:10 a.m. -
1 stop7h 57m
Tue 8/123:45 p.m. -
1 stop6h 10m
Deal found 31/8C$ 525
Fri 25/97:00 a.m. -
2 stops9h 35m
Mon 5/103:20 p.m. -
2 stops6h 29m
Deal found 30/8C$ 526
Fri 25/92:50 p.m. -
1 stop10h 31m
Tue 6/103:00 p.m. -
1 stop6h 55m
Deal found 31/8C$ 536
Fri 18/95:15 a.m. -
1 stop5h 45m
Mon 21/93:40 p.m. -
1 stop6h 55m
Deal found 28/8C$ 538
Sun 4/107:00 a.m. -
2 stops9h 35m
Thu 8/103:20 p.m. -
2 stops6h 29m
Deal found 29/8C$ 541
Fri 13/116:40 a.m. -
2 stops7h 00m
Mon 16/1112:20 p.m. -
2 stops9h 25m
Deal found 31/8C$ 541
Sat 10/107:15 a.m. -
2 stops8h 10m
Sat 17/108:45 a.m. -
1 stop5h 15m
Deal found 31/8C$ 543
Sat 10/106:25 a.m. -
1 stop5h 52m
Thu 15/1011:05 a.m. -
1 stop6h 05m
Deal found 30/8C$ 544
Fri 25/93:30 p.m. -
1 stop5h 03m
Mon 5/109:29 a.m. -
1 stop9h 41m
Deal found 30/8C$ 640

Find flight deals from Halifax to Chicago

Round-trip from

C$ 497

One-way from

C$ 266

Popular in

January

Cheapest in

December

Average price

C$ 476

Good round-trip deal

C$ 809 or less

Good one-way deal

C$ 330 or less
Air Canada
  • Air Canada
  • 25/9-5/10
  • 2 total stops
  • 12h 09m total
  • Halifax to Chicago
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Air Canada
  • Air Canada
  • 17/9
  • 1 total stop
  • 5h 50m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 26 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 47 potential savings vs. average RT price).
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Average for round-trip flights in August 2026
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Price to beat on a round-trip flight from Halifax Intl to Chicago (CHI).
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Price to beat on a one-way flight from Halifax Intl to Chicago (CHI).
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Cheapflights Fare Finder

 
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 Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

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

2 stops9h 35m

Chicago Midway

Mon 5/10

3:20 p.m.-11:49 p.m.

2 stops6h 29m

C$ 526

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 25/9

2:50 p.m.-11:21 p.m.

1 stop10h 31m

Chicago O'Hare Intl

Tue 6/10

3:00 p.m.-11:55 p.m.

1 stop6h 55m

C$ 536

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 13/11

6:40 a.m.-11:40 a.m.

2 stops7h 00m

Chicago O'Hare Intl

Mon 16/11

12:20 p.m.-11:45 p.m.

2 stops9h 25m

C$ 541

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 25/9

2:50 p.m.-11:21 p.m.

1 stop10h 31m

Chicago O'Hare Intl

Mon 5/10

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

1 stop5h 55m

C$ 556

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 25/9

2:50 p.m.-11:21 p.m.

1 stop10h 31m

Chicago O'Hare Intl

Fri 2/10

3:00 p.m.-11:55 p.m.

1 stop6h 55m

C$ 558

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 5/12

6:40 a.m.-5:30 p.m.

2 stops12h 50m

Chicago O'Hare Intl

Thu 10/12

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

2 stops10h 00m

C$ 575
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 13/2

5:10 a.m.-11:07 a.m.

1 stop7h 57m

Chicago O'Hare Intl

Mon 15/2

3:45 p.m.-11:55 p.m.

1 stop6h 10m

C$ 579

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 2/11

2:10 p.m.-12:01 a.m.

1 stop11h 51m

Chicago O'Hare Intl

Thu 5/11

9:48 p.m.-1:24 p.m.

1 stop13h 36m

C$ 583

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 22/1

2:10 p.m.-10:15 p.m.

1 stop10h 05m

Chicago O'Hare Intl

Sun 24/1

5:55 a.m.-1:24 p.m.

1 stop5h 29m

C$ 583

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 15/9

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

1 stop11h 38m

Chicago O'Hare Intl

Wed 16/9

1:30 p.m.-11:55 p.m.

1 stop8h 25m

C$ 624

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/8

Showing 1-10 of 36 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

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, December is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 432). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 958). 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?

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.

How much does it cost to fly round-trip from Halifax to Chicago?

Airfare is typical for this route at the moment.
Halifax to Chicago flights typically cost between C$ 352 and C$ 519 in September.
The cheapest round-trip price found within the last 5 days was C$ 479 on United Airlines (29 Sep-3 Oct).

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

Montreal (YUL) – chosen by Cheapflights users on 43% of one-stop itineraries from Halifax to Chicago on Cheapflights.

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

Detroit (DTW) is the most affordable 1-stop option, with an average round-trip price of C$ 493.

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

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?

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

Reviews of airlines servicing Chicago

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
458 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,151 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
WestJet
7.2
Good
3,444 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,566 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Food

7.6

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

Related info for your journey

  • 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 0 outbound flights to Chicago per day. 1 airline has flights to Chicago from Halifax Intl on a regular basis.

  • How long is the flight from Halifax to Chicago?

    For as low as C$ 640, Porter Airlines can have you in Chicago from Halifax in 5h 03m. The distance from Halifax to Chicago is about 1981 km. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Halifax to Chicago round-trip?

    Air Canada, at C$ 268, was found to be the cheapest airline from Halifax to Chicago.. Users have found that Air Canada is 55% 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 (93%), Envoy Air (93%), Qatar Airways (89%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 689 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 304 while the most popular route, (Halifax Intl - Chicago Midway) is currently priced at C$ 526.

  • 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, December is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 432). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 958). 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

Top airline flying from Halifax to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 268AverageC$ 609FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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