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 13/1. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
14 Jan — 21 Jan1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in September or January, booked 64 days in advance, depart on a Monday or Wednesday and return on a Wednesday
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 15 December 2025.
Wed 31/129:00 a.m.YHZ - ORD
2 stops15h 24mMultiple Airlines
Tue 6/15:00 a.m.ORD - YHZ
1 stop9h 15mMultiple Airlines
Deal found 13/12C$ 558
Tue 30/128:45 a.m.YHZ - ORD
1 stop27h 33mMultiple Airlines
Tue 6/15:00 a.m.ORD - YHZ
1 stop9h 15mMultiple Airlines
Deal found 13/12C$ 571
Wed 31/129:00 a.m.YHZ - ORD
1 stop12h 02mMultiple Airlines
Mon 5/13:26 p.m.ORD - YHZ
1 stop22h 49mMultiple Airlines
Deal found 13/12C$ 595
Wed 31/129:00 a.m.YHZ - ORD
2 stops15h 24mMultiple Airlines
Wed 7/15:29 p.m.ORD - YHZ
1 stop22h 02mMultiple Airlines
Deal found 14/12C$ 596
Wed 31/125:35 a.m.YHZ - ORD
2 stops9h 26mAir Canada
Wed 31/123:55 p.m.ORD - YHZ
1 stop6h 31mAir Canada
Deal found 13/12C$ 665
Wed 31/125:35 a.m.YHZ - ORD
2 stops9h 26mAir Canada
Thu 1/17:15 a.m.ORD - YHZ
1 stop14h 51mAir Canada
Deal found 13/12C$ 719
Wed 31/125:35 a.m.YHZ - ORD
2 stops9h 26mAir Canada
Tue 6/18:45 p.m.ORD - YHZ
2 stops12h 19mAir Canada
Deal found 13/12C$ 722
Tue 30/127:00 a.m.YHZ - ORD
1 stop14h 58mAir Canada
Sun 4/16:00 a.m.ORD - YHZ
1 stop15h 54mAir Canada
Deal found 13/12C$ 724
Wed 31/125:35 a.m.YHZ - ORD
2 stops9h 26mAir Canada
Sun 4/16:00 a.m.ORD - YHZ
1 stop15h 54mAir Canada
Deal found 13/12C$ 730
Wed 31/129:00 a.m.YHZ - MDW
1 stop14h 58mMultiple Airlines
Fri 2/14:15 p.m.MDW - YHZ
2 stops18h 20mMultiple Airlines
Deal found 13/12C$ 753
Fri 26/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Mon 29/1211:00 a.m.MDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 14/12C$ 761
Wed 31/129:00 a.m.YHZ - MDW
1 stop14h 58mMultiple Airlines
Thu 1/17:44 a.m.MDW - YHZ
2 stops11h 21mMultiple Airlines
Deal found 13/12C$ 774
Best flights from Halifax to Chicago
Discover carefully curated flight deals from Halifax to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 15 December 2025.
Sat 28/28:30 a.m.YHZ - MDW
1 stop5h 25mPorter Airlines
Mon 9/311:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 14/12C$ 449
Fri 30/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Sun 1/27:00 a.m.ORD - YHZ
2 stops25h 50mMultiple Airlines
Deal found 14/12C$ 508
Thu 29/111:35 a.m.YHZ - ORD
1 stop8h 13mMultiple Airlines
Sun 1/28:40 p.m.ORD - YHZ
1 stop12h 10mMultiple Airlines
Deal found 13/12C$ 519
Thu 12/38:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Sun 15/311:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 13/12C$ 584
Fri 30/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Sat 31/15:32 p.m.ORD - YHZ
2 stops21h 59mMultiple Airlines
Deal found 14/12C$ 541
Fri 30/18:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Sat 31/11:26 p.m.MDW - YHZ
2 stops10h 15mMultiple Airlines
Deal found 14/12C$ 545
Thu 12/26:40 a.m.YHZ - MDW
2 stops10h 40mPorter Airlines
Sun 15/211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 15/12C$ 611
Fri 30/16:30 a.m.YHZ - ORD
1 stop8h 00mPorter Airlines
Sun 1/23:37 p.m.ORD - YHZ
1 stop6h 50mPorter Airlines
Deal found 13/12C$ 636
Wed 31/129:00 a.m.YHZ - ORD
1 stop12h 02mMultiple Airlines
Mon 5/13:26 p.m.ORD - YHZ
1 stop22h 49mMultiple Airlines
Deal found 13/12C$ 595
Wed 28/18:30 a.m.YHZ - MDW
1 stop27h 35mPorter Airlines
Sat 31/112:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 13/12C$ 643
Wed 31/129:00 a.m.YHZ - ORD
2 stops15h 24mMultiple Airlines
Wed 7/15:29 p.m.ORD - YHZ
1 stop22h 02mMultiple Airlines
Deal found 14/12C$ 596
Thu 29/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Sat 31/15:32 p.m.ORD - YHZ
2 stops21h 59mMultiple Airlines
Deal found 14/12C$ 602
Fri 30/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Mon 2/22:50 p.m.ORD - YHZ
2 stops18h 00mMultiple Airlines
Deal found 14/12C$ 607
Tue 6/17:00 a.m.YHZ - ORD
2 stops14h 02mMultiple Airlines
Tue 20/15:15 a.m.ORD - YHZ
2 stops18h 26mMultiple Airlines
Deal found 13/12C$ 617
Fri 30/18:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Mon 2/211:05 a.m.MDW - YHZ
1 stop7h 05mMultiple Airlines
Deal found 14/12C$ 626
Tue 6/16:00 a.m.YHZ - MDW
2 stops8h 48mMultiple Airlines
Tue 20/111:05 a.m.MDW - YHZ
1 stop7h 05mMultiple Airlines
Deal found 13/12C$ 657
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 15 December 2025 and is based on user searches.
Sat 3/18:45 a.m.YHZ - ORD
1 stop31h 36mMultiple Airlines
Tue 6/15:00 a.m.ORD - YHZ
1 stop9h 15mMultiple Airlines
Deal found 13/12C$ 527
Fri 9/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Fri 16/15:15 a.m.ORD - YHZ
2 stops27h 35mMultiple Airlines
Deal found 12/12C$ 552
Fri 16/18:20 p.m.YHZ - ORD
2 stops23h 32mMultiple Airlines
Mon 19/17:20 a.m.ORD - YHZ
2 stops25h 30mMultiple Airlines
Deal found 13/12C$ 493
Wed 28/16:40 a.m.YHZ - ORD
2 stops13h 12mMultiple Airlines
Sat 31/112:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 14/12C$ 509
Wed 28/16:00 a.m.YHZ - MDW
2 stops8h 46mMultiple Airlines
Sun 1/21:00 p.m.MDW - YHZ
1 stop26h 31mMultiple Airlines
Deal found 14/12C$ 552
Thu 29/16:00 a.m.YHZ - ORD
1 stop13h 48mMultiple Airlines
Sun 1/22:00 p.m.ORD - YHZ
1 stop9h 41mMultiple Airlines
Deal found 14/12C$ 414
Thu 29/16:00 a.m.YHZ - MDW
2 stops8h 46mMultiple Airlines
Sun 1/21:00 p.m.MDW - YHZ
1 stop26h 31mMultiple Airlines
Deal found 13/12C$ 520
Fri 30/18:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Sun 1/21:00 p.m.MDW - YHZ
1 stop26h 31mMultiple Airlines
Deal found 14/12C$ 487
Fri 30/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Sun 1/27:00 a.m.ORD - YHZ
2 stops25h 50mMultiple Airlines
Deal found 14/12C$ 508
Fri 30/18:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Mon 2/21:00 p.m.MDW - YHZ
2 stops19h 50mMultiple Airlines
Deal found 14/12C$ 522
Fri 30/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Sat 31/15:32 p.m.ORD - YHZ
2 stops21h 59mMultiple Airlines
Deal found 14/12C$ 541
Fri 30/18:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Sat 31/11:26 p.m.MDW - YHZ
2 stops10h 15mMultiple Airlines
Deal found 14/12C$ 545
One-way flights from Halifax to Chicago
Search for one-way flight options from Halifax to Chicago. Find affordable one-way fares based on user searches. Data last updated 15 December 2025.
Tue 13/111:35 a.m.YHZ - ORD
2 stops14h 11mMultiple Airlines
Deal found 14/12C$ 248
Fri 16/110:40 p.m.YHZ - ORD
2 stops17h 59mMultiple Airlines
Deal found 14/12C$ 249
Thu 15/16:40 a.m.YHZ - ORD
2 stops15h 01mMultiple Airlines
Deal found 15/12C$ 255
Tue 27/16:00 a.m.YHZ - ORD
2 stops19h 46mMultiple Airlines
Deal found 13/12C$ 257
Mon 12/16:00 a.m.YHZ - ORD
2 stops31h 22mMultiple Airlines
Deal found 15/12C$ 259
Wed 14/16:30 a.m.YHZ - ORD
1 stop7h 55mPorter Airlines
Deal found 15/12C$ 266
Mon 12/16:30 a.m.YHZ - ORD
1 stop8h 00mPorter Airlines
Deal found 13/12C$ 267
Tue 13/16:30 a.m.YHZ - ORD
1 stop7h 55mPorter Airlines
Deal found 15/12C$ 270
Tue 27/16:40 a.m.YHZ - MDW
3 stops31h 25mMultiple Airlines
Deal found 13/12C$ 284
Sun 18/18:30 a.m.YHZ - MDW
2 stops17h 32mMultiple Airlines
Deal found 14/12C$ 300
Mon 2/310:40 p.m.YHZ - MDW
1 stop13h 25mMultiple Airlines
Deal found 14/12C$ 326
Tue 27/16:00 a.m.YHZ - MDW
2 stops8h 49mWestJet
Deal found 13/12C$ 332
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 15 December 2025.
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 15 December 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 - MDW
YHZMDW
Halifax Intl
Sat 28/2
8:30 a.m.-11:55 a.m.
1 stop5h 25m
Chicago Midway
Mon 9/3
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 449
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 30/1
8:45 a.m.-5:52 p.m.
1 stop11h 07m
Chicago O'Hare Intl
Sun 1/2
7:00 a.m.-10:50 a.m.
2 stops25h 50m
C$ 508
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 29/1
11:35 a.m.-5:48 p.m.
1 stop8h 13m
Chicago O'Hare Intl
Sun 1/2
8:40 p.m.-10:50 a.m.
1 stop12h 10m
C$ 519
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 30/1
8:45 a.m.-5:52 p.m.
1 stop11h 07m
Chicago O'Hare Intl
Sat 31/1
5:32 p.m.-5:31 p.m.
2 stops21h 59m
C$ 541
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Fri 30/1
8:45 a.m.-7:52 p.m.
1 stop13h 07m
Chicago Midway
Sat 31/1
1:26 p.m.-1:41 a.m.
2 stops10h 15m
C$ 545
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Thu 12/3
8:30 a.m.-3:20 p.m.
1 stop8h 50m
Chicago Midway
Sun 15/3
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 584
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 31/12
9:00 a.m.-7:02 p.m.
1 stop12h 02m
Chicago O'Hare Intl
Mon 5/1
3:26 p.m.-4:15 p.m.
1 stop22h 49m
C$ 595
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 31/12
9:00 a.m.-10:24 p.m.
2 stops15h 24m
Chicago O'Hare Intl
Wed 7/1
5:29 p.m.-5:31 p.m.
1 stop22h 02m
C$ 596
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 29/1
8:45 a.m.-5:52 p.m.
1 stop11h 07m
Chicago O'Hare Intl
Sat 31/1
5:32 p.m.-5:31 p.m.
2 stops21h 59m
C$ 602
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 30/1
8:45 a.m.-5:52 p.m.
1 stop11h 07m
Chicago O'Hare Intl
Mon 2/2
2:50 p.m.-10:50 a.m.
2 stops18h 00m
C$ 607
Flights are sorted by cheapest round-trip flights first.
Deals found on 14/12
Showing 1-10 of 29 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 12 December 2025.
To ensure you get the cheapest price possible for a flight from Halifax to Chicago, you should look to book at least 63 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, September is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 138). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 607). 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 15 December 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 54% on your trip compared to booking a flight at noon.
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 49% 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.
Newark (EWR) is the most affordable 1-stop option, with an average round-trip price of C$ 401.
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 Toronto (YTZ) have the shortest average one-way travel time for 1-stop routes: 5h 30m.
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 Newark (EWR) offer the fastest connection on this route, with an average layover time of 1h 42m.
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 15 December 2025.
Read through reviews of airlines operating flights from Halifax to Chicago, such as Porter Airlines,United Airlines, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
It's good. Planes are new and fresh. WiFi is best and stands out
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. 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$ 449, Porter Airlines can have you in Chicago from Halifax in 5h 25m. The distance from Halifax to Chicago is about 1981 km.
What are the cheapest airlines flying from Halifax to Chicago round-trip?
United Airlines, at C$ 225, 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 56% 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%), Envoy Air (100%), SkyWest Airlines (75%).
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$ 138). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 607). 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.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 15 December 2025.
Browse through other flights departing from Halifax. Flights are based on user searches made on Cheapflights and were last updated on 15 December 2025.
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 15 December 2025.
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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