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 29/1. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
30 Jan — 6 Feb1
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 March, booked 64 days in advance, depart on a Tuesday or Monday and return on a Monday
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 31 December 2025.
Wed 31/125:50 a.m.YHZ - ORD
1 stop11h 03mMultiple Airlines
Sat 10/18:27 p.m.ORD - YHZ
1 stop19h 04mMultiple Airlines
Deal found 30/12C$ 991
Wed 31/125:50 a.m.YHZ - ORD
1 stop11h 03mMultiple Airlines
Tue 6/19:34 a.m.ORD - YHZ
2 stops12h 20mMultiple Airlines
Deal found 30/12C$ 1,005
Wed 31/121:10 p.m.YHZ - ORD
1 stop8h 13mAmerican Airlines
Tue 6/13:37 p.m.ORD - YHZ
1 stop6h 45mAmerican Airlines
Deal found 30/12C$ 1,057
Wed 31/121:10 p.m.YHZ - ORD
1 stop8h 13mAmerican Airlines
Mon 5/13:04 p.m.ORD - YHZ
1 stop7h 18mAmerican Airlines
Deal found 30/12C$ 1,146
Tue 30/128:45 a.m.YHZ - ORD
1 stop11h 06mMultiple Airlines
Tue 6/14:38 p.m.ORD - YHZ
2 stops42h 47mMultiple Airlines
Deal found 30/12C$ 1,280
Wed 31/125:50 a.m.YHZ - ORD
1 stop11h 03mMultiple Airlines
Mon 5/14:38 p.m.ORD - YHZ
2 stops16h 12mMultiple Airlines
Deal found 30/12C$ 1,303
Tue 30/1211:20 p.m.YHZ - ORD
1 stop15h 41mAir Canada
Tue 6/13:35 p.m.ORD - YHZ
1 stop6h 31mAir Canada
Deal found 30/12C$ 1,392
Wed 31/129:00 a.m.YHZ - MDW
2 stops34h 38mMultiple Airlines
Tue 6/111:05 a.m.MDW - YHZ
1 stop7h 05mMultiple Airlines
Deal found 31/12C$ 1,620
Tue 30/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Tue 6/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 30/12C$ 1,754
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 31 December 2025.
Fri 6/21:10 p.m.YHZ - ORD
2 stops22h 02mMultiple Airlines
Wed 11/212:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 30/12C$ 400
Sun 15/36:40 a.m.YHZ - MDW
2 stops10h 40mPorter Airlines
Wed 18/311:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 31/12C$ 504
Thu 12/36:55 a.m.YHZ - ORD
1 stop6h 23mAir Canada
Sun 15/33:35 p.m.ORD - YHZ
1 stop6h 46mAir Canada
Deal found 29/12C$ 663
Thu 12/28:20 p.m.YHZ - MDW
1 stop15h 50mMultiple Airlines
Tue 17/211:05 a.m.MDW - YHZ
1 stop21h 45mMultiple Airlines
Deal found 29/12C$ 446
Tue 24/31:20 p.m.YHZ - ORD
2 stops12h 18mMultiple Airlines
Mon 30/32:20 p.m.ORD - YHZ
1 stop15h 08mMultiple Airlines
Deal found 30/12C$ 516
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 29/12C$ 576
Wed 25/36:55 a.m.YHZ - ORD
1 stop12h 29mMultiple Airlines
Mon 30/36:59 p.m.ORD - YHZ
2 stops27h 23mMultiple Airlines
Deal found 30/12C$ 550
Thu 12/26:10 p.m.YHZ - ORD
1 stop21h 25mMultiple Airlines
Tue 17/212:44 p.m.ORD - YHZ
2 stops34h 57mMultiple Airlines
Deal found 30/12C$ 554
Fri 6/27:05 p.m.YHZ - MDW
2 stops18h 45mPorter Airlines
Wed 11/211:00 a.m.MDW - YHZ
2 stops10h 58mPorter Airlines
Deal found 30/12C$ 686
Fri 6/28:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Wed 11/26:35 p.m.MDW - YHZ
2 stops38h 15mMultiple Airlines
Deal found 30/12C$ 565
Mon 5/110:40 p.m.YHZ - MDW
1 stop13h 30mMultiple Airlines
Mon 12/14:31 p.m.MDW - YHZ
2 stops31h 10mMultiple Airlines
Deal found 28/12C$ 572
Tue 24/38:45 a.m.YHZ - ORD
1 stop16h 53mMultiple Airlines
Sun 29/35:40 p.m.ORD - YHZ
2 stops15h 10mMultiple Airlines
Deal found 30/12C$ 594
Tue 24/38:45 a.m.YHZ - ORD
1 stop16h 53mMultiple Airlines
Sat 28/39:50 a.m.ORD - YHZ
2 stops13h 51mMultiple Airlines
Deal found 30/12C$ 617
Direct flights from Halifax to Chicago
Explore direct flight options from Halifax to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 31 December 2025.
Mon 1/65:00 p.m.YHZ - ORD
Nonstop3h 43mAir Canada
Wed 3/610:35 a.m.ORD - YHZ
Nonstop3h 12mAir Canada
Deal found 30/12C$ 720
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 31 December 2025 and is based on user searches.
Tue 30/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Tue 6/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 30/12C$ 1,754
Wed 31/125:50 a.m.YHZ - ORD
1 stop11h 03mMultiple Airlines
Sat 10/18:27 p.m.ORD - YHZ
1 stop19h 04mMultiple Airlines
Deal found 30/12C$ 991
Wed 31/125:50 a.m.YHZ - ORD
1 stop11h 03mMultiple Airlines
Tue 6/19:34 a.m.ORD - YHZ
2 stops12h 20mMultiple Airlines
Deal found 30/12C$ 1,005
Wed 31/121:10 p.m.YHZ - ORD
1 stop8h 13mAmerican Airlines
Tue 6/13:37 p.m.ORD - YHZ
1 stop6h 45mAmerican Airlines
Deal found 30/12C$ 1,057
Wed 31/129:00 a.m.YHZ - MDW
2 stops34h 38mMultiple Airlines
Tue 6/111:05 a.m.MDW - YHZ
1 stop7h 05mMultiple Airlines
Deal found 31/12C$ 1,620
Thu 1/15:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Sat 10/17:15 a.m.ORD - YHZ
1 stop6h 32mAir Canada
Deal found 30/12C$ 1,006
Thu 1/19:00 a.m.YHZ - ORD
2 stops28h 00mMultiple Airlines
Sat 10/18:27 p.m.ORD - YHZ
1 stop19h 04mMultiple Airlines
Deal found 30/12C$ 1,053
Thu 1/14:50 p.m.YHZ - MDW
2 stops19h 15mPorter Airlines
Sat 10/112:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 30/12C$ 1,108
Mon 5/110:40 p.m.YHZ - MDW
1 stop13h 30mMultiple Airlines
Mon 12/14:31 p.m.MDW - YHZ
2 stops31h 10mMultiple Airlines
Deal found 28/12C$ 572
Mon 5/11:20 p.m.YHZ - ORD
2 stops21h 11mMultiple Airlines
Mon 12/12:20 p.m.ORD - YHZ
1 stop15h 08mMultiple Airlines
Deal found 28/12C$ 711
Mon 5/18:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Mon 12/111:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 28/12C$ 839
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 31 December 2025.
Thu 29/18:45 a.m.YHZ - ORD
1 stop27h 50mMultiple Airlines
Deal found 31/12C$ 197
Tue 27/16:40 a.m.YHZ - ORD
2 stops13h 12mMultiple Airlines
Deal found 31/12C$ 212
Sun 1/28:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Deal found 31/12C$ 216
Mon 2/31:10 p.m.YHZ - ORD
2 stops22h 12mMultiple Airlines
Deal found 30/12C$ 235
Mon 26/16:40 a.m.YHZ - ORD
2 stops32h 33mMultiple Airlines
Deal found 30/12C$ 237
Sat 31/16:00 a.m.YHZ - ORD
2 stops15h 44mMultiple Airlines
Deal found 30/12C$ 240
Fri 30/110:40 p.m.YHZ - ORD
3 stops19h 55mMultiple Airlines
Deal found 31/12C$ 242
Mon 2/210:40 p.m.YHZ - ORD
2 stops25h 24mMultiple Airlines
Deal found 31/12C$ 249
Sun 1/26:00 a.m.YHZ - MDW
3 stops31h 45mMultiple Airlines
Deal found 31/12C$ 298
Fri 13/210:40 p.m.YHZ - MDW
2 stops36h 14mMultiple Airlines
Deal found 30/12C$ 423
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 31 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 31 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 - ORD
YHZORD
Halifax Intl
Fri 6/2
1:10 p.m.-9:12 a.m.
2 stops22h 02m
Chicago O'Hare Intl
Wed 11/2
12:44 p.m.-5:31 p.m.
1 stop26h 47m
C$ 400
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Thu 12/2
8:20 p.m.-10:10 a.m.
1 stop15h 50m
Chicago Midway
Tue 17/2
11:05 a.m.-10:50 a.m.
1 stop21h 45m
C$ 446
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Sun 15/3
6:40 a.m.-3:20 p.m.
2 stops10h 40m
Chicago Midway
Wed 18/3
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 504
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Tue 24/3
1:20 p.m.-11:38 p.m.
2 stops12h 18m
Chicago O'Hare Intl
Mon 30/3
2:20 p.m.-7:28 a.m.
1 stop15h 08m
C$ 516
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 25/3
6:55 a.m.-5:24 p.m.
1 stop12h 29m
Chicago O'Hare Intl
Mon 30/3
6:59 p.m.-12:22 a.m.
2 stops27h 23m
C$ 550
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 12/2
6:10 p.m.-1:35 p.m.
1 stop21h 25m
Chicago O'Hare Intl
Tue 17/2
12:44 p.m.-1:41 a.m.
2 stops34h 57m
C$ 554
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Fri 6/2
8:45 a.m.-7:52 p.m.
1 stop13h 07m
Chicago Midway
Wed 11/2
6:35 p.m.-10:50 a.m.
2 stops38h 15m
C$ 565
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Mon 5/1
10:40 p.m.-10:10 a.m.
1 stop13h 30m
Chicago Midway
Mon 12/1
4:31 p.m.-1:41 a.m.
2 stops31h 10m
C$ 572
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$ 576
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Tue 24/3
8:45 a.m.-11:38 p.m.
1 stop16h 53m
Chicago O'Hare Intl
Sun 29/3
5:40 p.m.-10:50 a.m.
2 stops15h 10m
C$ 594
Flights are sorted by cheapest round-trip flights first.
Deals found on 31/12
Showing 1-10 of 27 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 26 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$ 137). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 604). 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’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 50% 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.
Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 358.
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 31 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$ 504, Porter Airlines can have you in Chicago from Halifax in 10h 40m. 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$ 223, 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 57% 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: SkyWest Airlines (100%), Air Canada (100%), United Airlines (100%).
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$ 137). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 604). 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 31 December 2025.
Browse through other flights departing from Halifax. Flights are based on user searches made on Cheapflights and were last updated on 31 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 31 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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