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 24/2. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
24 Dec — 31 Dec1
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
Find 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 24 November 2025.
Mon 8/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Sun 14/1211:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 23/11C$ 467
Mon 8/1210:40 p.m.YHZ - MDW
1 stop13h 25mMultiple Airlines
Sun 14/124:15 p.m.MDW - YHZ
1 stop27h 40mMultiple Airlines
Deal found 23/11C$ 486
Sat 13/128:25 a.m.YHZ - MDW
1 stop5h 25mPorter Airlines
Tue 30/1211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 21/11C$ 532
Mon 15/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Mon 29/1211:00 a.m.MDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 21/11C$ 594
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Mon 29/1211:00 a.m.MDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 24/11C$ 653
Mon 8/127:00 a.m.YHZ - ORD
1 stop8h 01mAir Canada
Sun 14/127:05 a.m.ORD - YHZ
1 stop6h 42mAir Canada
Deal found 23/11C$ 653
Sat 27/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Mon 29/123:55 p.m.ORD - YHZ
1 stop6h 31mAir Canada
Deal found 23/11C$ 654
Wed 24/129:00 a.m.YHZ - ORD
1 stop12h 02mMultiple Airlines
Sun 28/125:05 a.m.ORD - YHZ
2 stops34h 33mMultiple Airlines
Deal found 21/11C$ 667
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 22/11C$ 704
Thu 25/126:55 a.m.YHZ - ORD
1 stop6h 23mAir Canada
Thu 1/18:40 p.m.ORD - YHZ
1 stop10h 45mAir Canada
Deal found 24/11C$ 704
Mon 22/128:45 a.m.YHZ - MDW
1 stop15h 13mMultiple Airlines
Tue 30/124:15 p.m.MDW - YHZ
2 stops21h 51mMultiple Airlines
Deal found 24/11C$ 725
Sat 13/126:00 a.m.YHZ - ORD
2 stops12h 22mWestJet
Tue 30/129:41 a.m.ORD - YHZ
2 stops14h 00mWestJet
Deal found 21/11C$ 730
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 24 November 2025.
Mon 13/48:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Thu 16/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 21/11C$ 371
Sun 11/18:45 a.m.YHZ - ORD
1 stop12h 32mMultiple Airlines
Tue 13/17:45 p.m.ORD - YHZ
2 stops27h 56mMultiple Airlines
Deal found 24/11C$ 516
Thu 8/15:05 a.m.YHZ - ORD
1 stop6h 08mAir Canada
Thu 15/13:55 p.m.ORD - YHZ
1 stop6h 31mAir Canada
Deal found 24/11C$ 561
Mon 8/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Sun 14/1211:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 23/11C$ 467
Thu 8/18:20 p.m.YHZ - ORD
2 stops27h 19mMultiple Airlines
Thu 15/13:25 p.m.ORD - YHZ
3 stops28h 30mMultiple Airlines
Deal found 24/11C$ 522
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 22/11C$ 513
Thu 22/18:20 p.m.YHZ - ORD
2 stops27h 19mMultiple Airlines
Sun 25/17:00 a.m.ORD - YHZ
2 stops25h 50mMultiple Airlines
Deal found 22/11C$ 546
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 24/11C$ 644
Wed 15/411:20 a.m.YHZ - ORD
1 stop5h 35mAir Canada
Thu 16/43:45 p.m.ORD - YHZ
1 stop6h 20mAir Canada
Deal found 21/11C$ 644
Wed 15/41:10 p.m.YHZ - ORD
1 stop8h 25mPorter Airlines
Thu 16/49:40 a.m.ORD - YHZ
2 stops9h 25mPorter Airlines
Deal found 23/11C$ 644
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 24 November 2025 and is based on user searches.
Mon 8/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Sun 14/1211:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 23/11C$ 467
Mon 8/1210:40 p.m.YHZ - MDW
1 stop13h 25mMultiple Airlines
Sun 14/124:15 p.m.MDW - YHZ
1 stop27h 40mMultiple Airlines
Deal found 23/11C$ 486
Mon 8/127:00 a.m.YHZ - ORD
1 stop8h 01mAir Canada
Sun 14/127:05 a.m.ORD - YHZ
1 stop6h 42mAir Canada
Deal found 23/11C$ 653
Sat 13/128:25 a.m.YHZ - MDW
1 stop5h 25mPorter Airlines
Tue 30/1211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 21/11C$ 532
Sat 13/126:00 a.m.YHZ - ORD
2 stops12h 22mWestJet
Tue 30/129:41 a.m.ORD - YHZ
2 stops14h 00mWestJet
Deal found 21/11C$ 730
Mon 15/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Mon 29/1211:00 a.m.MDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 21/11C$ 594
Mon 22/128:45 a.m.YHZ - MDW
1 stop15h 13mMultiple Airlines
Tue 30/124:15 p.m.MDW - YHZ
2 stops21h 51mMultiple Airlines
Deal found 24/11C$ 725
Wed 24/129:00 a.m.YHZ - ORD
1 stop12h 02mMultiple Airlines
Sun 28/125:05 a.m.ORD - YHZ
2 stops34h 33mMultiple Airlines
Deal found 21/11C$ 667
Thu 25/126:55 a.m.YHZ - ORD
1 stop6h 23mAir Canada
Thu 1/18:40 p.m.ORD - YHZ
1 stop10h 45mAir Canada
Deal found 24/11C$ 704
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Mon 29/1211:00 a.m.MDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 24/11C$ 653
Sat 27/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Mon 29/123:55 p.m.ORD - YHZ
1 stop6h 31mAir Canada
Deal found 23/11C$ 654
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 22/11C$ 704
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 24 November 2025.
Tue 24/28:45 a.m.YHZ - ORD
1 stop9h 34mMultiple Airlines
Deal found 21/11C$ 251
Tue 23/126:55 a.m.YHZ - ORD
1 stop30h 19mMultiple Airlines
Deal found 24/11C$ 255
Thu 21/57:40 a.m.YHZ - ORD
1 stop11h 03mWestJet
Deal found 24/11C$ 257
Wed 21/16:40 a.m.YHZ - ORD
2 stops30h 01mMultiple Airlines
Deal found 24/11C$ 259
Thu 8/16:30 a.m.YHZ - ORD
1 stop8h 00mPorter Airlines
Deal found 24/11C$ 269
Wed 24/129:00 a.m.YHZ - ORD
1 stop12h 02mMultiple Airlines
Deal found 24/11C$ 271
Tue 6/16:55 a.m.YHZ - ORD
1 stop30h 19mMultiple Airlines
Deal found 22/11C$ 272
Tue 20/16:30 a.m.YHZ - ORD
1 stop7h 55mPorter Airlines
Deal found 24/11C$ 276
Sat 21/26:30 a.m.YHZ - ORD
1 stop8h 03mPorter Airlines
Deal found 21/11C$ 278
Tue 6/16:55 a.m.YHZ - MDW
2 stops41h 22mMultiple Airlines
Deal found 22/11C$ 279
Mon 19/16:30 a.m.YHZ - ORD
1 stop8h 00mPorter Airlines
Deal found 22/11C$ 282
Sun 25/16:00 a.m.YHZ - ORD
2 stops31h 22mMultiple Airlines
Deal found 22/11C$ 283
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 24 November 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 24 November 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
Mon 13/4
8:25 a.m.-3:20 p.m.
2 stops8h 55m
Chicago Midway
Thu 16/4
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 371
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Mon 8/12
8:25 a.m.-3:20 p.m.
1 stop8h 55m
Chicago Midway
Sun 14/12
11:00 a.m.-11:54 p.m.
2 stops10h 54m
C$ 467
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$ 513
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Sun 11/1
8:45 a.m.-7:17 p.m.
1 stop12h 32m
Chicago O'Hare Intl
Tue 13/1
7:45 p.m.-1:41 a.m.
2 stops27h 56m
C$ 516
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 8/1
8:20 p.m.-9:39 p.m.
2 stops27h 19m
Chicago O'Hare Intl
Thu 15/1
3:25 p.m.-9:55 p.m.
3 stops28h 30m
C$ 522
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 22/1
8:20 p.m.-9:39 p.m.
2 stops27h 19m
Chicago O'Hare Intl
Sun 25/1
7:00 a.m.-10:50 a.m.
2 stops25h 50m
C$ 546
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 8/1
5:05 a.m.-9:13 a.m.
1 stop6h 08m
Chicago O'Hare Intl
Thu 15/1
3:55 p.m.-12:26 a.m.
1 stop6h 31m
C$ 561
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Thu 12/3
6:55 a.m.-11:18 a.m.
1 stop6h 23m
Chicago O'Hare Intl
Sun 15/3
3:35 p.m.-12:21 a.m.
1 stop6h 46m
C$ 644
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 15/4
11:20 a.m.-2:55 p.m.
1 stop5h 35m
Chicago O'Hare Intl
Thu 16/4
3:45 p.m.-12:05 a.m.
1 stop6h 20m
C$ 644
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 15/4
1:10 p.m.-7:35 p.m.
1 stop8h 25m
Chicago O'Hare Intl
Thu 16/4
9:40 a.m.-9:05 p.m.
2 stops9h 25m
C$ 644
Flights are sorted by cheapest round-trip flights first.
Deals found on 21/11
Showing 1-10 of 24 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 21 November 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$ 141). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 622). 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 24 November 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 43% 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$ 411.
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 24 November 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$ 371, Porter Airlines can have you in Chicago from Halifax in 8h 55m. 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$ 230, 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 (90%).
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$ 141). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 622). 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 24 November 2025.
Browse through other flights departing from Halifax. Flights are based on user searches made on Cheapflights and were last updated on 24 November 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 24 November 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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