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Cheap flights from Halifax to Chicago from C$ 261

YHZ — CHI
23 Oct — 30 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

Sat 3/106:25 a.m. -
1 stop5h 47m
Sat 10/1011:05 a.m. -
1 stop6h 05m
Deal found 18/9C$ 431
Tue 6/106:25 a.m. -
1 stop5h 47m
Thu 12/117:05 a.m. -
1 stop6h 50m
Deal found 19/9C$ 452
Tue 6/106:25 a.m. -
1 stop5h 47m
Fri 13/114:30 p.m. -
1 stop7h 28m
Deal found 19/9C$ 459
Tue 24/1111:25 a.m. -
1 stop5h 27m
Sun 29/111:55 p.m. -
2 stops8h 20m
Deal found 19/9C$ 461
Sat 3/104:50 p.m. -
Nonstop3h 50m
Sat 10/108:45 a.m. -
1 stop5h 15m
Deal found 18/9C$ 464
Fri 13/115:00 a.m. -
1 stop6h 23m
Mon 16/114:30 p.m. -
1 stop7h 28m
Deal found 18/9C$ 466
Sat 31/106:05 a.m. -
1 stop7h 02m
Tue 3/111:55 p.m. -
1 stop5h 40m
Deal found 20/9C$ 468
Thu 26/117:15 a.m. -
2 stops10h 23m
Sun 29/111:55 p.m. -
2 stops8h 20m
Deal found 19/9C$ 475
Sat 21/116:05 a.m. -
2 stops11h 33m
Wed 25/113:45 p.m. -
1 stop6h 30m
Deal found 20/9C$ 479
Sat 3/108:00 p.m. -
1 stop17h 00m
Sat 10/103:20 p.m. -
2 stops23h 19m
Deal found 20/9C$ 518
Sat 3/106:20 a.m. -
1 stop10h 15m
Sat 10/1011:45 a.m. -
1 stop10h 07m
Deal found 18/9C$ 545
Sat 3/103:30 p.m. -
2 stops9h 14m
Sat 10/109:29 a.m. -
1 stop9h 41m
Deal found 18/9C$ 551

Find flight deals from Halifax to Chicago

Round-trip from

C$ 431

One-way from

C$ 261

Popular in

January

Cheapest in

December

Average price

C$ 496

Good round-trip deal

C$ 886 or less

Good one-way deal

C$ 558 or less
Air Canada
  • Air Canada
  • 3/10-10/10
  • 2 total stops
  • 11h 52m total
  • Halifax to Chicago
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Air Canada
  • Air Canada
  • 20/10-31/12
  • 1 total stop
  • 5h 47m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 27 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 September 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 - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 17/11

6:05 a.m.-11:07 a.m.

1 stop7h 02m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 261

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 20/11

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

1 stop7h 57m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 261

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 21/10

9:00 a.m.-2:55 p.m.

1 stop7h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 268
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 13/11

5:00 a.m.-9:23 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 270

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 19/10

2:50 p.m.-10:28 p.m.

1 stop9h 38m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 271

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 23/10

2:50 p.m.-10:28 p.m.

1 stop9h 38m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 273

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 20/10

7:15 a.m.-2:55 p.m.

2 stops9h 40m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 275

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 18/11

7:15 a.m.-3:38 p.m.

2 stops10h 23m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 277

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 2/11

6:40 a.m.-4:35 p.m.

2 stops11h 55m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 312

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 17/10

5:15 a.m.-9:48 a.m.

1 stop6h 33m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 313

Flights are sorted by cheapest round-trip flights first.

Deals found on 19/9

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

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$ 506). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 969). 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 below average for this route at the moment.
Halifax to Chicago flights typically cost between C$ 485 and C$ 610 in October.
The cheapest round-trip price found within the last 5 days was C$ 431 on Air Canada (3 Oct-10 Oct).

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

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?

Newark (EWR) is the most affordable 1-stop option, with an average round-trip price of C$ 467.

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 Newark (EWR) offer the fastest connection on this route, with an average layover time of 1h 18m.

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
462 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.4
Good
10,226 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
WestJet
7.2
Good
3,446 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,665 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Food

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

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$ 431, Air Canada can have you in Chicago from Halifax in 5h 47m. The distance from Halifax to Chicago is about 1988 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$ 271, 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 (100%), Qatar Airways (100%), Envoy Air (100%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 745 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 474 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 520.

  • 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$ 506). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 969). 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$ 271AverageC$ 607FlexibilityNo 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.

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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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