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Cheap flights from Halifax to Chicago from C$ 309

YHZ — CHI
2 Nov — 9 Nov1
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

Tue 17/1111:25 a.m. -
1 stop5h 37m
Tue 24/113:40 p.m. -
1 stop6h 35m
Deal found 3/10C$ 553
Tue 10/116:05 a.m. -
1 stop7h 02m
Tue 10/113:40 p.m. -
1 stop6h 35m
Deal found 3/10C$ 557
Tue 8/122:10 p.m. -
1 stop6h 31m
Wed 9/129:34 p.m. -
1 stop13h 50m
Deal found 28/9C$ 578
Fri 13/115:15 a.m. -
1 stop7h 52m
Mon 16/113:50 p.m. -
1 stop6h 25m
Deal found 3/10C$ 583
Tue 8/126:05 a.m. -
1 stop7h 02m
Wed 9/128:45 a.m. -
2 stops9h 03m
Deal found 28/9C$ 586
Fri 20/1111:25 a.m. -
1 stop5h 35m
Sun 29/117:05 a.m. -
1 stop6h 50m
Deal found 2/10C$ 590
Wed 25/115:10 a.m. -
1 stop7h 57m
Sun 29/114:30 p.m. -
1 stop7h 28m
Deal found 1/10C$ 600
Sat 31/105:15 a.m. -
1 stop7h 52m
Sat 7/113:40 p.m. -
1 stop6h 35m
Deal found 3/10C$ 603
Fri 30/105:00 a.m. -
1 stop6h 23m
Sun 8/117:05 a.m. -
1 stop6h 50m
Deal found 2/10C$ 604
Wed 18/116:40 a.m. -
2 stops7h 00m
Wed 2/1212:20 p.m. -
2 stops9h 25m
Deal found 29/9C$ 607
Fri 30/106:00 a.m. -
2 stops12h 47m
Sun 8/119:29 a.m. -
2 stops14h 26m
Deal found 2/10C$ 899
Mon 19/107:25 a.m. -
2 stops9h 10m
Fri 23/103:20 p.m. -
2 stops6h 29m
Deal found 30/9C$ 949

Find flight deals from Halifax to Chicago

Round-trip from

C$ 553

One-way from

C$ 322

Popular in

November

Cheapest in

August

Average price

C$ 678

Good round-trip deal

C$ 899 or less
Air Canada
  • Air Canada
  • 17/11-24/11
  • 2 total stops
  • 12h 12m total
  • Halifax to Chicago
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Air Canada
  • Air Canada
  • 28/10-31/12
  • 1 total stop
  • 7h 52m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 163 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 68 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Price to beat on a round-trip 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

Thu 31/12

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

1 stop10h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 355

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 28/10

6:30 a.m.-3:37 p.m.

2 stops35h 07m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 366

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 27/10

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

1 stop11h 51m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 366

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 26/10

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

1 stop11h 51m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 366
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sun 27/12

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

2 stops7h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 372

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 1/1

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

2 stops7h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 372

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 16/11

10:00 a.m.-6:30 p.m.

3 stops34h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 373

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 4/12

2:10 p.m.-8:06 p.m.

1 stop7h 56m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 385

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sun 1/11

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

1 stop11h 51m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 386

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 30/11

10:25 a.m.-3:38 p.m.

1 stop7h 13m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 388

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/9

Showing 1-10 of 37 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, August is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 526). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 983). 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$ 499 and C$ 678 in November.
The cheapest round-trip price found within the last 5 days was C$ 553 on Air Canada (17 Nov-24 Nov).

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$ 473.

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,WestJet, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
466 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

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
466 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

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
3,450 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

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
11,712 reviews
Porter Airlines
8.0
Very good
466 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

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$ 578, United Airlines can have you in Chicago from Halifax in 6h 31m. 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$ 275, was found to be the cheapest airline from Halifax to Chicago.. Users have found that Air Canada is 59% 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 (88%), Qatar Airways (88%), Envoy Air (88%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 944 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 771 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 645.

  • 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, August is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 526). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 983). 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$ 275AverageC$ 626FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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