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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
7 Feb — 14 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 Monday or Tuesday and return on a Monday
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 8 January 2026.
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 8 January 2026.
Sat 16/56:45 a.m.YHZ - MDW
2 stops11h 39mPorter Airlines
Wed 20/59:40 a.m.MDW - YHZ
2 stops11h 49mPorter Airlines
Deal found 7/1C$ 352
Sat 14/28:30 a.m.YHZ - MDW
1 stop5h 25mPorter Airlines
Wed 18/211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 7/1C$ 373
Mon 20/48:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Tue 21/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 5/1C$ 398
Thu 5/28:45 a.m.YHZ - ORD
1 stop27h 50mMultiple Airlines
Tue 10/212:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 8/1C$ 402
Thu 22/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Wed 28/17:20 a.m.ORD - YHZ
2 stops25h 30mMultiple Airlines
Deal found 8/1C$ 417
Sat 21/37:00 a.m.YHZ - MDW
2 stops6h 50mPorter Airlines
Wed 25/311:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 8/1C$ 469
Thu 22/18:20 p.m.YHZ - MDW
1 stop15h 50mMultiple Airlines
Wed 28/11:20 p.m.MDW - YHZ
2 stops26h 11mMultiple Airlines
Deal found 8/1C$ 475
Thu 15/18:45 a.m.YHZ - ORD
1 stop12h 56mMultiple Airlines
Sun 25/112:21 p.m.ORD - YHZ
1 stop27h 10mMultiple Airlines
Deal found 7/1C$ 477
Tue 28/48:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Fri 1/59:40 a.m.MDW - YHZ
2 stops11h 49mPorter Airlines
Deal found 7/1C$ 478
Sat 16/53:30 p.m.YHZ - ORD
1 stop27h 13mWestJet
Wed 20/55:30 p.m.ORD - YHZ
1 stop12h 40mWestJet
Deal found 7/1C$ 492
Sat 16/53:30 p.m.YHZ - ORD
2 stops16h 01mMultiple Airlines
Wed 20/59:04 a.m.ORD - YHZ
2 stops13h 20mMultiple Airlines
Deal found 7/1C$ 543
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 8 January 2026.
Sat 16/56:45 a.m.YHZ - MDW
2 stops11h 39mPorter Airlines
Wed 20/59:40 a.m.MDW - YHZ
2 stops11h 49mPorter Airlines
Deal found 7/1C$ 352
Thu 5/28:45 a.m.YHZ - ORD
1 stop27h 50mMultiple Airlines
Tue 10/212:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 8/1C$ 402
Sat 16/53:30 p.m.YHZ - ORD
1 stop27h 13mWestJet
Wed 20/55:30 p.m.ORD - YHZ
1 stop12h 40mWestJet
Deal found 7/1C$ 492
Mon 20/48:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Tue 21/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 5/1C$ 398
Thu 22/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Wed 28/17:20 a.m.ORD - YHZ
2 stops25h 30mMultiple Airlines
Deal found 8/1C$ 417
Sat 14/28:30 a.m.YHZ - MDW
1 stop5h 25mPorter Airlines
Wed 18/211:05 a.m.MDW - YHZ
2 stops6h 51mPorter Airlines
Deal found 7/1C$ 433
Thu 22/18:20 p.m.YHZ - MDW
1 stop15h 50mMultiple Airlines
Wed 28/11:20 p.m.MDW - YHZ
2 stops26h 11mMultiple Airlines
Deal found 8/1C$ 475
Sat 21/37:00 a.m.YHZ - MDW
2 stops6h 50mPorter Airlines
Wed 25/311:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 8/1C$ 469
Tue 28/43:30 p.m.YHZ - ORD
2 stops28h 34mWestJet
Fri 1/55:03 p.m.ORD - YHZ
2 stops25h 42mWestJet
Deal found 7/1C$ 579
Tue 28/48:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Fri 1/59:40 a.m.MDW - YHZ
2 stops11h 49mPorter Airlines
Deal found 7/1C$ 478
Sat 16/53:30 p.m.YHZ - ORD
2 stops16h 01mMultiple Airlines
Wed 20/59:04 a.m.ORD - YHZ
2 stops13h 20mMultiple Airlines
Deal found 7/1C$ 543
Sun 22/28:45 a.m.YHZ - ORD
1 stop14h 12mMultiple Airlines
Sun 1/37:35 a.m.ORD - YHZ
2 stops40h 06mMultiple Airlines
Deal found 6/1C$ 553
Tue 28/41:20 p.m.YHZ - ORD
2 stops11h 23mMultiple Airlines
Fri 1/55:30 p.m.ORD - YHZ
1 stop12h 40mMultiple Airlines
Deal found 7/1C$ 579
Sat 21/37:00 a.m.YHZ - ORD
2 stops14h 45mMultiple Airlines
Wed 25/312:44 p.m.ORD - YHZ
2 stops34h 57mMultiple Airlines
Deal found 8/1C$ 581
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 8 January 2026 and is based on user searches.
Thu 15/18:45 a.m.YHZ - ORD
1 stop12h 56mMultiple Airlines
Sun 25/112:21 p.m.ORD - YHZ
1 stop27h 10mMultiple Airlines
Deal found 7/1C$ 477
Thu 15/18:30 a.m.YHZ - MDW
1 stop27h 35mPorter Airlines
Sun 25/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 7/1C$ 708
Thu 22/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Wed 28/17:20 a.m.ORD - YHZ
2 stops25h 30mMultiple Airlines
Deal found 8/1C$ 417
Thu 22/18:20 p.m.YHZ - MDW
1 stop15h 50mMultiple Airlines
Wed 28/11:20 p.m.MDW - YHZ
2 stops26h 11mMultiple Airlines
Deal found 8/1C$ 475
Thu 22/18:30 a.m.YHZ - MDW
1 stop27h 35mPorter Airlines
Wed 28/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 8/1C$ 713
Thu 5/28:45 a.m.YHZ - ORD
1 stop27h 50mMultiple Airlines
Tue 10/212:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 8/1C$ 402
Thu 5/28:30 a.m.YHZ - MDW
1 stop27h 40mPorter Airlines
Tue 10/211:05 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 8/1C$ 616
Sat 14/28:30 a.m.YHZ - MDW
1 stop5h 25mPorter Airlines
Wed 18/211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 7/1C$ 373
Sat 14/28:30 a.m.YHZ - ORD
2 stops18h 10mMultiple Airlines
Wed 18/25:15 a.m.ORD - YHZ
1 stop9h 00mMultiple Airlines
Deal found 7/1C$ 553
Sun 22/28:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Sun 1/311:00 a.m.MDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 6/1C$ 706
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 8 January 2026.
Thu 5/28:30 a.m.YHZ - ORD
3 stops28h 05mMultiple Airlines
Deal found 6/1C$ 203
Tue 3/26:40 a.m.YHZ - ORD
2 stops17h 04mMultiple Airlines
Deal found 7/1C$ 211
Mon 2/28:30 a.m.YHZ - ORD
3 stops39h 14mMultiple Airlines
Deal found 6/1C$ 220
Sat 14/28:30 a.m.YHZ - MDW
1 stop5h 25mPorter Airlines
Deal found 7/1C$ 225
Fri 6/21:10 p.m.YHZ - ORD
2 stops22h 02mMultiple Airlines
Deal found 7/1C$ 234
Sun 8/26:40 a.m.YHZ - ORD
3 stops37h 49mMultiple Airlines
Deal found 6/1C$ 242
Tue 3/37:00 a.m.YHZ - ORD
3 stops28h 22mMultiple Airlines
Deal found 6/1C$ 245
Wed 4/28:20 p.m.YHZ - ORD
3 stops28h 56mMultiple Airlines
Deal found 6/1C$ 246
Mon 2/310:40 p.m.YHZ - ORD
2 stops35h 33mMultiple Airlines
Deal found 6/1C$ 249
Wed 4/36:40 a.m.YHZ - MDW
2 stops33h 46mMultiple Airlines
Deal found 7/1C$ 256
Fri 20/21:10 p.m.YHZ - MDW
2 stops27h 45mMultiple Airlines
Deal found 6/1C$ 281
Sat 14/26:00 a.m.YHZ - MDW
2 stops30h 06mWestJet
Deal found 7/1C$ 359
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 8 January 2026.
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 16/5
6:45 a.m.-4:24 p.m.
2 stops11h 39m
Chicago Midway
Wed 20/5
9:40 a.m.-11:29 p.m.
2 stops11h 49m
C$ 352
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Mon 20/4
8:25 a.m.-3:20 p.m.
2 stops8h 55m
Chicago Midway
Tue 21/4
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 398
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 5/2
8:45 a.m.-10:35 a.m.
1 stop27h 50m
Chicago O'Hare Intl
Tue 10/2
12:44 p.m.-5:31 p.m.
1 stop26h 47m
C$ 402
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 22/1
8:45 a.m.-5:52 p.m.
1 stop11h 07m
Chicago O'Hare Intl
Wed 28/1
7:20 a.m.-10:50 a.m.
2 stops25h 30m
C$ 417
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Sat 14/2
8:30 a.m.-11:55 a.m.
1 stop5h 25m
Chicago Midway
Wed 18/2
11:05 a.m.-7:56 p.m.
2 stops6h 51m
C$ 433
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Sat 21/3
7:00 a.m.-11:50 a.m.
2 stops6h 50m
Chicago Midway
Wed 25/3
11:00 a.m.-11:54 p.m.
2 stops10h 54m
C$ 469
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Thu 22/1
8:20 p.m.-10:10 a.m.
1 stop15h 50m
Chicago Midway
Wed 28/1
1:20 p.m.-5:31 p.m.
2 stops26h 11m
C$ 475
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Tue 28/4
8:30 a.m.-3:20 p.m.
1 stop8h 50m
Chicago Midway
Fri 1/5
9:40 a.m.-11:29 p.m.
2 stops11h 49m
C$ 478
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Sat 16/5
3:30 p.m.-4:43 p.m.
1 stop27h 13m
Chicago O'Hare Intl
Wed 20/5
5:30 p.m.-8:10 a.m.
1 stop12h 40m
C$ 492
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Sat 16/5
3:30 p.m.-5:31 a.m.
2 stops16h 01m
Chicago O'Hare Intl
Wed 20/5
9:04 a.m.-12:24 a.m.
2 stops13h 20m
C$ 543
Flights are sorted by cheapest round-trip flights first.
Deals found on 6/1
Showing 1-10 of 28 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 2 January 2026.
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 February is currently the most expensive (average of C$ 705). 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 51% 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$ 362.
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 8 January 2026.
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$ 352, Porter Airlines can have you in Chicago from Halifax in 11h 39m. The distance from Halifax to Chicago is about 1981 km. This flight may include one or multiple stops.
What are the cheapest airlines flying from Halifax to Chicago round-trip?
United Airlines, at C$ 226, 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 58% cheaper than the other options available to this destination.
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 February is currently the most expensive (average of C$ 705). 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 8 January 2026.
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 8 January 2026.
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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