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Cheap flights from Halifax to Chicago from C$ 282

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 26/8. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
8 Jul — 15 Jul1
1 adult

Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in January or February, booked 51 days in advance, depart on a Monday or Wednesday and return on a Wednesday

Cheap 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 3 July 2025.

Round-trip from

C$ 414

One-way from

C$ 282

Popular in

June

Cheapest in

January

Average price

C$ 576

Good round-trip deal

C$ 603 or less

Good one-way deal

C$ 460 or less
American Airlines
  • American Airlines
  • 18/7-19/7
  • 2 total stops
  • 14h 39m total
  • Halifax to Chicago
Delta
  • Delta
  • 26/8
  • 2 total stops
  • 11h 33m total
  • Halifax to Chicago
Highest demand for flights based on searches. 9% potential increase in price (C$ 77 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Halifax Intl to Chicago (CHI).
Price to beat on a one-way flight from Halifax Intl to Chicago (CHI).

Find flight deals from Halifax to Chicago

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 3 July 2025.

Fri 18/73:25 p.m.YHZ - ORD
2 stops11h 34mAmerican Airlines
Sat 19/78:09 a.m.ORD - YHZ
Nonstop3h 05mAmerican Airlines
Deal found 3/7C$ 414
Sat 16/81:15 p.m.YHZ - ORD
1 stop7h 59mDelta
Sat 6/97:15 a.m.ORD - YHZ
2 stops13h 28mDelta
Deal found 1/7C$ 522
Sat 16/86:40 a.m.YHZ - MDW
2 stops7h 48mDelta
Sat 6/99:31 a.m.MDW - YHZ
2 stops11h 12mDelta
Deal found 1/7C$ 523
Sat 12/77:15 a.m.YHZ - ORD
2 stops9h 49mAir Canada
Sat 19/79:55 a.m.ORD - YHZ
2 stops9h 16mAir Canada
Deal found 1/7C$ 566
Mon 21/76:45 a.m.YHZ - MDW
2 stops11h 39mPorter Airlines
Thu 24/79:40 a.m.MDW - YHZ
2 stops11h 49mPorter Airlines
Deal found 3/7C$ 572
Sat 19/75:00 p.m.YHZ - ORD
Nonstop3h 45mUnited Airlines
Sat 26/72:27 p.m.ORD - YHZ
1 stop7h 28mUnited Airlines
Deal found 1/7C$ 591
Fri 15/88:00 a.m.YHZ - ORD
3 stops29h 43mMultiple Airlines
Fri 22/86:56 a.m.ORD - YHZ
2 stops14h 33mMultiple Airlines
Deal found 1/7C$ 606
Sat 12/79:00 a.m.YHZ - MDW
1 stop13h 22mMultiple Airlines
Sat 19/79:40 a.m.MDW - YHZ
1 stop23h 20mMultiple Airlines
Deal found 1/7C$ 609
Sat 2/88:30 a.m.YHZ - ORD
2 stops15h 04mWestJet
Fri 8/89:00 a.m.ORD - YHZ
2 stops11h 40mWestJet
Deal found 1/7C$ 691
Sat 19/78:30 a.m.YHZ - MDW
2 stops15h 12mWestJet
Sat 26/77:21 p.m.MDW - YHZ
2 stops20h 19mWestJet
Deal found 1/7C$ 750

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 3 July 2025.
Use the filters below to find and compare flights from Halifax to Chicago that are best for you.

Fly from

Halifax

Fly to

Chicago

Route

Depart

Return

Price

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 18/7

3:25 p.m.-12:59 a.m.

2 stops11h 34m

Chicago O'Hare Intl

Sat 19/7

8:09 a.m.-1:14 p.m.

Nonstop3h 05m

C$ 414

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 16/8

1:15 p.m.-7:14 p.m.

1 stop7h 59m

Chicago O'Hare Intl

Sat 6/9

7:15 a.m.-10:43 p.m.

2 stops13h 28m

C$ 522

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 16/8

6:40 a.m.-3:28 p.m.

2 stops10h 48m

Chicago Midway

Sat 6/9

9:31 a.m.-10:43 p.m.

2 stops11h 12m

C$ 523

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 17/8

5:05 a.m.-9:09 a.m.

1 stop6h 04m

Chicago O'Hare Intl

Wed 3/9

8:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 571

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 21/7

6:45 a.m.-4:24 p.m.

2 stops11h 39m

Chicago Midway

Thu 24/7

9:40 a.m.-11:29 p.m.

2 stops11h 49m

C$ 572

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 19/7

5:00 p.m.-6:45 p.m.

Nonstop3h 45m

Chicago O'Hare Intl

Sat 26/7

2:27 p.m.-11:55 p.m.

1 stop7h 28m

C$ 591

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 15/8

8:00 a.m.-11:43 a.m.

3 stops29h 43m

Chicago O'Hare Intl

Fri 22/8

6:56 a.m.-11:29 p.m.

2 stops14h 33m

C$ 606

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 2/8

8:30 a.m.-9:34 p.m.

2 stops15h 04m

Chicago O'Hare Intl

Fri 8/8

9:00 a.m.-10:40 p.m.

2 stops11h 40m

C$ 691

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 19/7

8:30 a.m.-9:42 p.m.

2 stops15h 12m

Chicago Midway

Sat 26/7

7:21 p.m.-5:40 p.m.

2 stops20h 19m

C$ 750

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 16/8

11:00 p.m.-1:03 p.m.

2 stops16h 03m

Chicago Midway

Sat 23/8

7:17 p.m.-4:10 p.m.

3 stops18h 53m

C$ 1,071

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 18 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Halifax to Chicago. Price data was last updated on 27 June 2025.

To ensure you get the cheapest price possible for a flight from Halifax to Chicago, you should look to book at least 50 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.

What is the cheapest month to book a flight from Halifax to Chicago?

Currently, January is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 261). Flying from Halifax to Chicago in March is currently the most expensive (average of C$ 352). 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 3 July 2025.

A simple way to save on the total cost of your ticket is to fly from Halifax to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 42% on your trip compared to booking a flight in the afternoon.

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 3 July 2025.
Read through reviews of airlines operating flights from Halifax to Chicago, such as Porter Airlines,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Food

7.7

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Food

7.7

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
8.0
Very good

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Food

7.7

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Food

7.7

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Food

7.7

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Food

7.7

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 0 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Halifax Intl on a regular basis.

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

    American Airlines, at C$ 414, was found to be the cheapest airline from Halifax to Chicago.Alternate airlines to your destination round-trip include Delta and Air Canada. Users have found that American Airlines is 20% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Halifax to Chicago one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at C$ 282. Air Canada flights start at C$ 308 while deals on American Airlines start at C$ 316 one-way.

  • 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 (100%), American Airlines (100%), Air Canada (100%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 628 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 368 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 544.

  • 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, January is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 261). Flying from Halifax to Chicago in March is currently the most expensive (average of C$ 352). 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 4 airlines flying from Halifax to Chicago

Discover the top 4 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 3 July 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 358AverageC$ 494FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 396AverageC$ 424FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 403AverageC$ 551FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 501AverageC$ 611FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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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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