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
3 Feb — 10 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
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 4 January 2026.
Sun 1/26:40 a.m.YHZ - MDW
2 stops10h 40mPorter Airlines
Sun 8/211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 3/1C$ 354
Mon 20/48:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Tue 21/411:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 3/1C$ 397
Sun 1/26:00 a.m.YHZ - MDW
1 stop11h 20mMultiple Airlines
Sun 8/24:15 p.m.MDW - YHZ
1 stop16h 35mMultiple Airlines
Deal found 3/1C$ 445
Fri 6/28:45 a.m.YHZ - ORD
1 stop12h 56mMultiple Airlines
Wed 11/25:32 p.m.ORD - YHZ
2 stops39h 18mMultiple Airlines
Deal found 2/1C$ 457
Fri 30/110:40 p.m.YHZ - MDW
1 stop15h 10mMultiple Airlines
Mon 2/211:00 a.m.MDW - YHZ
1 stop7h 10mMultiple Airlines
Deal found 3/1C$ 460
Fri 30/110:40 p.m.YHZ - MDW
2 stops12h 12mMultiple Airlines
Sun 1/24:15 p.m.MDW - YHZ
1 stop16h 35mMultiple Airlines
Deal found 2/1C$ 471
Fri 30/18:30 a.m.YHZ - ORD
3 stops17h 16mMultiple Airlines
Sun 1/28:43 p.m.ORD - YHZ
2 stops18h 48mMultiple Airlines
Deal found 3/1C$ 552
Sun 1/28:45 a.m.YHZ - ORD
1 stop27h 56mMultiple Airlines
Sun 8/24:38 p.m.ORD - YHZ
2 stops40h 12mMultiple Airlines
Deal found 3/1C$ 566
Fri 30/18:30 a.m.YHZ - ORD
3 stops17h 16mMultiple Airlines
Mon 2/28:43 p.m.ORD - YHZ
3 stops25h 15mMultiple Airlines
Deal found 3/1C$ 573
Fri 30/16:00 a.m.YHZ - ORD
2 stops12h 30mWestJet
Sun 1/25:25 p.m.ORD - YHZ
2 stops30h 16mWestJet
Deal found 3/1C$ 607
Wed 21/16:00 a.m.YHZ - ORD
2 stops17h 03mMultiple Airlines
Fri 23/112:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 3/1C$ 618
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 4 January 2026.
Sun 1/26:40 a.m.YHZ - MDW
2 stops10h 40mPorter Airlines
Sun 8/211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 3/1C$ 354
Sun 1/26:00 a.m.YHZ - MDW
1 stop11h 20mMultiple Airlines
Sun 8/24:15 p.m.MDW - YHZ
1 stop16h 35mMultiple Airlines
Deal found 3/1C$ 445
Fri 30/16:00 a.m.YHZ - ORD
2 stops12h 30mWestJet
Sun 1/25:25 p.m.ORD - YHZ
2 stops30h 16mWestJet
Deal found 3/1C$ 607
Mon 20/48:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Tue 21/411:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 3/1C$ 397
Fri 6/28:45 a.m.YHZ - ORD
1 stop12h 56mMultiple Airlines
Wed 11/25:32 p.m.ORD - YHZ
2 stops39h 18mMultiple Airlines
Deal found 2/1C$ 457
Fri 30/110:40 p.m.YHZ - MDW
2 stops12h 12mMultiple Airlines
Mon 2/211:05 a.m.MDW - YHZ
1 stop21h 45mMultiple Airlines
Deal found 3/1C$ 471
Fri 30/110:40 p.m.YHZ - MDW
2 stops12h 12mMultiple Airlines
Sun 1/24:15 p.m.MDW - YHZ
1 stop16h 35mMultiple Airlines
Deal found 2/1C$ 471
Thu 5/38:20 a.m.YHZ - ORD
1 stop31h 15mWestJet
Mon 9/32:20 p.m.ORD - YHZ
1 stop15h 08mWestJet
Deal found 2/1C$ 623
Fri 30/18:30 a.m.YHZ - ORD
3 stops17h 16mMultiple Airlines
Sun 1/28:43 p.m.ORD - YHZ
2 stops18h 48mMultiple Airlines
Deal found 3/1C$ 552
Sun 1/28:45 a.m.YHZ - ORD
1 stop27h 56mMultiple Airlines
Sun 8/24:38 p.m.ORD - YHZ
2 stops40h 12mMultiple Airlines
Deal found 3/1C$ 566
Wed 21/16:00 a.m.YHZ - ORD
2 stops17h 03mMultiple Airlines
Fri 23/112:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 3/1C$ 618
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 4 January 2026 and is based on user searches.
Wed 21/16:00 a.m.YHZ - ORD
2 stops17h 03mMultiple Airlines
Fri 23/112:44 p.m.ORD - YHZ
1 stop26h 47mMultiple Airlines
Deal found 3/1C$ 618
Fri 30/110:40 p.m.YHZ - MDW
1 stop15h 10mMultiple Airlines
Mon 2/211:00 a.m.MDW - YHZ
1 stop7h 10mMultiple Airlines
Deal found 3/1C$ 460
Fri 30/110:40 p.m.YHZ - MDW
2 stops12h 12mMultiple Airlines
Sun 1/24:15 p.m.MDW - YHZ
1 stop16h 35mMultiple Airlines
Deal found 2/1C$ 471
Fri 30/18:30 a.m.YHZ - ORD
3 stops17h 16mMultiple Airlines
Sun 1/28:43 p.m.ORD - YHZ
2 stops18h 48mMultiple Airlines
Deal found 3/1C$ 552
Fri 30/18:30 a.m.YHZ - ORD
3 stops17h 16mMultiple Airlines
Mon 2/28:43 p.m.ORD - YHZ
3 stops25h 15mMultiple Airlines
Deal found 3/1C$ 573
Fri 30/16:00 a.m.YHZ - ORD
2 stops12h 30mWestJet
Sun 1/25:25 p.m.ORD - YHZ
2 stops30h 16mWestJet
Deal found 3/1C$ 607
Sun 1/26:40 a.m.YHZ - MDW
2 stops10h 40mPorter Airlines
Sun 8/211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 3/1C$ 354
Sun 1/26:00 a.m.YHZ - MDW
1 stop11h 20mMultiple Airlines
Sun 8/24:15 p.m.MDW - YHZ
1 stop16h 35mMultiple Airlines
Deal found 3/1C$ 445
Sun 1/28:45 a.m.YHZ - ORD
1 stop27h 56mMultiple Airlines
Sun 8/24:38 p.m.ORD - YHZ
2 stops40h 12mMultiple Airlines
Deal found 3/1C$ 566
Fri 6/28:45 a.m.YHZ - ORD
1 stop12h 56mMultiple Airlines
Wed 11/25:32 p.m.ORD - YHZ
2 stops39h 18mMultiple Airlines
Deal found 2/1C$ 457
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 4 January 2026.
Thu 5/28:45 a.m.YHZ - ORD
1 stop27h 50mMultiple Airlines
Deal found 3/1C$ 246
Wed 4/28:30 a.m.YHZ - ORD
3 stops40h 06mMultiple Airlines
Deal found 3/1C$ 250
Mon 2/211:35 a.m.YHZ - ORD
2 stops25h 47mMultiple Airlines
Deal found 2/1C$ 258
Tue 3/26:40 a.m.YHZ - ORD
2 stops15h 01mMultiple Airlines
Deal found 2/1C$ 260
Thu 26/28:20 p.m.YHZ - ORD
2 stops37h 53mMultiple Airlines
Deal found 2/1C$ 265
Wed 4/311:35 a.m.YHZ - ORD
2 stops14h 12mMultiple Airlines
Deal found 2/1C$ 270
Sun 1/31:10 p.m.YHZ - ORD
1 stop8h 19mPorter Airlines
Deal found 2/1C$ 281
Mon 16/210:40 p.m.YHZ - ORD
2 stops25h 21mMultiple Airlines
Deal found 1/1C$ 288
Mon 16/27:00 a.m.YHZ - MDW
2 stops10h 20mPorter Airlines
Deal found 3/1C$ 325
Mon 16/26:00 a.m.YHZ - MDW
3 stops18h 29mMultiple Airlines
Deal found 3/1C$ 383
Sat 20/61:30 p.m.YHZ - MDW
2 stops22h 21mWestJet
Deal found 2/1C$ 439
Sat 20/63:30 p.m.YHZ - MDW
1 stop5h 01mDelta
Deal found 2/1C$ 542
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 4 January 2026.
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 4 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
Sun 1/2
6:40 a.m.-3:20 p.m.
2 stops10h 40m
Chicago Midway
Sun 8/2
11:00 a.m.-8:10 p.m.
1 stop7h 10m
C$ 354
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.-11:54 p.m.
2 stops10h 54m
C$ 397
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Sun 1/2
6:00 a.m.-3:20 p.m.
1 stop11h 20m
Chicago Midway
Sun 8/2
4:15 p.m.-10:50 a.m.
1 stop16h 35m
C$ 445
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 6/2
8:45 a.m.-7:41 p.m.
1 stop12h 56m
Chicago O'Hare Intl
Wed 11/2
5:32 p.m.-10:50 a.m.
2 stops39h 18m
C$ 457
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Fri 30/1
10:40 p.m.-8:52 a.m.
2 stops12h 12m
Chicago Midway
Mon 2/2
11:05 a.m.-10:50 a.m.
1 stop21h 45m
C$ 471
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Fri 30/1
10:40 p.m.-8:52 a.m.
2 stops12h 12m
Chicago Midway
Sun 1/2
4:15 p.m.-10:50 a.m.
1 stop16h 35m
C$ 471
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 30/1
8:30 a.m.-11:46 p.m.
3 stops17h 16m
Chicago O'Hare Intl
Sun 1/2
8:43 p.m.-5:31 p.m.
2 stops18h 48m
C$ 552
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Sun 1/2
8:45 a.m.-10:41 a.m.
1 stop27h 56m
Chicago O'Hare Intl
Sun 8/2
4:38 p.m.-10:50 a.m.
2 stops40h 12m
C$ 566
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 30/1
6:00 a.m.-4:30 p.m.
2 stops12h 30m
Chicago O'Hare Intl
Sun 1/2
5:25 p.m.-1:41 a.m.
2 stops30h 16m
C$ 607
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 21/1
6:00 a.m.-9:03 p.m.
2 stops17h 03m
Chicago O'Hare Intl
Fri 23/1
12:44 p.m.-5:31 p.m.
1 stop26h 47m
C$ 618
Flights are sorted by cheapest round-trip flights first.
Deals found on 2/1
Showing 1-10 of 25 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$ 137). Flying from Halifax to Chicago in February is currently the most expensive (average of C$ 700). 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.
How much does it cost to fly round-trip from Halifax to Chicago?
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$ 359.
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 4 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$ 354, 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$ 224, 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$ 137). Flying from Halifax to Chicago in February is currently the most expensive (average of C$ 700). 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 4 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 4 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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