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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
7 Jan — 14 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 8 December 2025.
Tue 30/126:55 a.m.YHZ - ORD
1 stop10h 47mMultiple Airlines
Wed 21/17:20 a.m.ORD - YHZ
2 stops25h 30mMultiple Airlines
Deal found 5/12C$ 489
Fri 26/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Wed 21/17:15 a.m.ORD - YHZ
1 stop6h 32mAir Canada
Deal found 5/12C$ 647
Fri 26/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
2 stops8h 05mPorter Airlines
Deal found 8/12C$ 673
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
2 stops8h 05mPorter Airlines
Deal found 6/12C$ 703
Thu 25/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Thu 1/112:50 p.m.ORD - YHZ
1 stop9h 16mAir Canada
Deal found 6/12C$ 707
Fri 26/1211:35 a.m.YHZ - ORD
3 stops22h 56mMultiple Airlines
Wed 21/15:15 a.m.ORD - YHZ
2 stops27h 35mMultiple Airlines
Deal found 5/12C$ 776
Thu 25/125:30 p.m.YHZ - MDW
1 stop18h 35mPorter Airlines
Mon 29/1211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 7/12C$ 837
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 December 2025.
Tue 14/48:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Wed 15/411:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 6/12C$ 379
Wed 28/18:20 p.m.YHZ - MDW
1 stop15h 50mMultiple Airlines
Sat 31/112:45 p.m.MDW - YHZ
1 stop5h 25mMultiple Airlines
Deal found 7/12C$ 439
Wed 28/16:00 a.m.YHZ - ORD
2 stops16h 47mWestJet
Sat 31/15:35 p.m.ORD - YHZ
2 stops30h 06mWestJet
Deal found 7/12C$ 568
Fri 26/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Wed 21/17:15 a.m.ORD - YHZ
1 stop6h 32mAir Canada
Deal found 5/12C$ 647
Wed 1/48:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Sun 5/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 6/12C$ 380
Thu 2/48:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Sun 5/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 6/12C$ 380
Sun 15/26:40 a.m.YHZ - MDW
2 stops10h 40mPorter Airlines
Sun 15/311:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 5/12C$ 489
Tue 30/126:55 a.m.YHZ - ORD
1 stop10h 47mMultiple Airlines
Wed 21/110:48 a.m.ORD - YHZ
1 stop28h 43mMultiple Airlines
Deal found 5/12C$ 594
Wed 1/45:35 a.m.YHZ - ORD
1 stop6h 33mAir Canada
Sun 5/43:45 p.m.ORD - YHZ
1 stop6h 20mAir Canada
Deal found 6/12C$ 647
Tue 14/411:20 a.m.YHZ - ORD
1 stop5h 35mAir Canada
Wed 15/43:45 p.m.ORD - YHZ
1 stop6h 20mAir Canada
Deal found 5/12C$ 649
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 6/12C$ 649
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 8 December 2025 and is based on user searches.
Thu 25/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Thu 1/112:50 p.m.ORD - YHZ
1 stop9h 16mAir Canada
Deal found 6/12C$ 707
Fri 26/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Wed 21/17:15 a.m.ORD - YHZ
1 stop6h 32mAir Canada
Deal found 5/12C$ 647
Fri 26/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
2 stops8h 05mPorter Airlines
Deal found 8/12C$ 673
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
2 stops8h 05mPorter Airlines
Deal found 6/12C$ 703
Tue 30/126:55 a.m.YHZ - ORD
1 stop10h 47mMultiple Airlines
Wed 21/17:20 a.m.ORD - YHZ
2 stops25h 30mMultiple Airlines
Deal found 5/12C$ 489
Fri 2/18:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Mon 19/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 6/12C$ 674
Wed 28/18:20 p.m.YHZ - MDW
1 stop15h 50mMultiple Airlines
Sat 31/112:45 p.m.MDW - YHZ
1 stop5h 25mMultiple Airlines
Deal found 7/12C$ 439
Wed 28/17:05 p.m.YHZ - MDW
2 stops17h 00mPorter Airlines
Sat 31/112:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 7/12C$ 547
Wed 28/16:00 a.m.YHZ - ORD
2 stops16h 47mWestJet
Sat 31/15:35 p.m.ORD - YHZ
2 stops30h 06mWestJet
Deal found 7/12C$ 568
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 7/12C$ 573
Wed 28/16:30 a.m.YHZ - ORD
1 stop7h 55mPorter Airlines
Sat 31/13:37 p.m.ORD - YHZ
1 stop6h 50mPorter Airlines
Deal found 7/12C$ 631
Wed 28/16:00 a.m.YHZ - MDW
2 stops13h 29mWestJet
Sat 31/15:00 p.m.MDW - YHZ
2 stops30h 41mWestJet
Deal found 7/12C$ 647
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 December 2025.
Wed 4/26:00 a.m.YHZ - ORD
2 stops42h 36mMultiple Airlines
Deal found 8/12C$ 228
Mon 9/26:00 a.m.YHZ - ORD
2 stops31h 22mMultiple Airlines
Deal found 8/12C$ 231
Tue 20/111:35 a.m.YHZ - ORD
2 stops14h 11mMultiple Airlines
Deal found 6/12C$ 247
Tue 3/211:35 a.m.YHZ - ORD
2 stops25h 47mMultiple Airlines
Deal found 6/12C$ 254
Wed 4/32:10 p.m.YHZ - ORD
2 stops49h 25mMultiple Airlines
Deal found 8/12C$ 258
Tue 6/11:20 p.m.YHZ - ORD
2 stops27h 01mMultiple Airlines
Deal found 7/12C$ 261
Tue 20/16:30 a.m.YHZ - ORD
1 stop7h 55mPorter Airlines
Deal found 6/12C$ 262
Wed 7/11:20 p.m.YHZ - ORD
2 stops30h 32mMultiple Airlines
Deal found 7/12C$ 264
Tue 20/111:35 a.m.YHZ - MDW
3 stops26h 30mMultiple Airlines
Deal found 6/12C$ 269
Mon 2/26:00 a.m.YHZ - ORD
2 stops12h 58mMultiple Airlines
Deal found 5/12C$ 271
Wed 4/26:30 a.m.YHZ - ORD
1 stop7h 55mPorter Airlines
Deal found 5/12C$ 272
Fri 6/211:10 a.m.YHZ - ORD
2 stops34h 34mMultiple Airlines
Deal found 6/12C$ 274
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 8 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 8 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
Tue 14/4
8:30 a.m.-3:20 p.m.
1 stop8h 50m
Chicago Midway
Wed 15/4
11:00 a.m.-11:54 p.m.
2 stops10h 54m
C$ 379
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Wed 1/4
8:30 a.m.-3:20 p.m.
1 stop8h 50m
Chicago Midway
Sun 5/4
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 380
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Thu 2/4
8:30 a.m.-3:20 p.m.
1 stop8h 50m
Chicago Midway
Sun 5/4
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 380
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Wed 28/1
8:20 p.m.-10:10 a.m.
1 stop15h 50m
Chicago Midway
Sat 31/1
12:45 p.m.-8:10 p.m.
1 stop5h 25m
C$ 439
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Sun 15/2
6:40 a.m.-3:20 p.m.
2 stops10h 40m
Chicago Midway
Sun 15/3
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 489
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 28/1
6:00 a.m.-8:47 p.m.
2 stops16h 47m
Chicago O'Hare Intl
Sat 31/1
5:35 p.m.-1:41 a.m.
2 stops30h 06m
C$ 568
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Tue 30/12
6:55 a.m.-3:42 p.m.
1 stop10h 47m
Chicago O'Hare Intl
Wed 21/1
10:48 a.m.-5:31 p.m.
1 stop28h 43m
C$ 594
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 26/12
5:35 a.m.-11:18 a.m.
1 stop7h 43m
Chicago O'Hare Intl
Wed 21/1
7:15 a.m.-3:47 p.m.
1 stop6h 32m
C$ 647
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 1/4
5:35 a.m.-10:08 a.m.
1 stop6h 33m
Chicago O'Hare Intl
Sun 5/4
3:45 p.m.-12:05 a.m.
1 stop6h 20m
C$ 647
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Tue 14/4
11:20 a.m.-2:55 p.m.
1 stop5h 35m
Chicago O'Hare Intl
Wed 15/4
3:45 p.m.-12:05 a.m.
1 stop6h 20m
C$ 649
Flights are sorted by cheapest round-trip flights first.
Deals found on 8/12
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 5 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$ 609). 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 8 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.
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 48% 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$ 403.
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 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$ 647, Porter Airlines can have you in Chicago from Halifax in 7h 43m. The distance from Halifax to Chicago is about 1988 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$ 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$ 609). 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 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 8 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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