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 20/1. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
22 Jan — 29 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 23 December 2025.
Sun 21/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Sun 28/1211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 20/12C$ 709
Fri 26/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 23/12C$ 834
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 22/12C$ 899
Fri 26/126:30 a.m.YHZ - ORD
1 stop8h 03mMultiple Airlines
Thu 1/16:02 p.m.ORD - YHZ
2 stops29h 39mMultiple Airlines
Deal found 21/12C$ 947
Thu 25/121:00 p.m.YHZ - ORD
1 stop7h 53mAir Canada
Thu 1/12:37 p.m.ORD - YHZ
1 stop7h 17mAir Canada
Deal found 22/12C$ 984
Fri 26/121:00 p.m.YHZ - ORD
1 stop7h 53mAir Canada
Fri 2/17:15 a.m.ORD - YHZ
1 stop6h 32mAir Canada
Deal found 21/12C$ 990
Fri 26/126:00 a.m.YHZ - ORD
2 stops13h 22mWestJet
Fri 2/16:02 p.m.ORD - YHZ
2 stops29h 39mWestJet
Deal found 22/12C$ 995
Fri 26/125:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Thu 1/12:37 p.m.ORD - YHZ
1 stop7h 17mAir Canada
Deal found 23/12C$ 1,002
Thu 25/126:10 p.m.YHZ - ORD
2 stops29h 24mWestJet
Thu 1/17:00 a.m.ORD - YHZ
2 stops16h 41mWestJet
Deal found 21/12C$ 1,023
Sun 21/121:15 p.m.YHZ - ORD
1 stop8h 30mAir Canada
Sun 28/1212:50 p.m.ORD - YHZ
1 stop6h 26mAir Canada
Deal found 20/12C$ 1,024
Thu 25/126:00 a.m.YHZ - MDW
2 stops28h 49mWestJet
Thu 1/16:08 p.m.MDW - YHZ
2 stops29h 33mWestJet
Deal found 21/12C$ 1,045
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 23 December 2025.
Tue 14/47:00 a.m.YHZ - MDW
2 stops10h 20mPorter Airlines
Wed 15/411:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 21/12C$ 319
Wed 4/21:20 p.m.YHZ - ORD
2 stops12h 27mMultiple Airlines
Wed 11/27:20 a.m.ORD - YHZ
2 stops25h 30mMultiple Airlines
Deal found 21/12C$ 414
Tue 27/16:00 a.m.YHZ - ORD
2 stops16h 47mWestJet
Sat 28/25:37 p.m.ORD - YHZ
2 stops30h 04mWestJet
Deal found 22/12C$ 585
Sat 10/16:55 a.m.YHZ - ORD
1 stop6h 11mAir Canada
Sat 17/110:00 a.m.ORD - YHZ
2 stops7h 44mAir Canada
Deal found 22/12C$ 611
Wed 4/24:50 p.m.YHZ - MDW
2 stops19h 20mPorter Airlines
Wed 11/211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 21/12C$ 505
Fri 16/110:40 p.m.YHZ - ORD
2 stops27h 06mMultiple Airlines
Mon 19/15:15 a.m.ORD - YHZ
2 stops27h 35mMultiple Airlines
Deal found 21/12C$ 515
Sat 10/16:40 a.m.YHZ - MDW
2 stops7h 10mPorter Airlines
Sat 17/112:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 22/12C$ 537
Fri 6/210:40 p.m.YHZ - ORD
2 stops24h 23mMultiple Airlines
Fri 13/22:20 p.m.ORD - YHZ
1 stop15h 08mMultiple Airlines
Deal found 22/12C$ 585
Fri 3/48:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Sun 5/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 22/12C$ 556
Wed 18/26:55 a.m.YHZ - ORD
1 stop16h 18mMultiple Airlines
Sat 21/24:42 p.m.ORD - YHZ
2 stops30h 59mMultiple Airlines
Deal found 21/12C$ 618
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 22/12C$ 595
Tue 27/16:30 a.m.YHZ - ORD
1 stop7h 55mPorter Airlines
Sat 28/21:21 p.m.ORD - YHZ
1 stop6h 16mPorter Airlines
Deal found 22/12C$ 617
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 23 December 2025 and is based on user searches.
Fri 26/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 23/12C$ 834
Fri 26/126:30 a.m.YHZ - ORD
1 stop8h 03mMultiple Airlines
Thu 1/16:02 p.m.ORD - YHZ
2 stops29h 39mMultiple Airlines
Deal found 21/12C$ 947
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 22/12C$ 899
Sat 10/16:40 a.m.YHZ - MDW
2 stops7h 10mPorter Airlines
Sat 17/112:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 22/12C$ 537
Sat 10/16:55 a.m.YHZ - ORD
1 stop6h 11mAir Canada
Sat 17/110:00 a.m.ORD - YHZ
2 stops7h 44mAir Canada
Deal found 22/12C$ 611
Fri 16/110:40 p.m.YHZ - ORD
2 stops27h 06mMultiple Airlines
Mon 19/15:15 a.m.ORD - YHZ
2 stops27h 35mMultiple Airlines
Deal found 21/12C$ 515
Fri 16/14:50 p.m.YHZ - MDW
2 stops21h 00mPorter Airlines
Mon 19/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 21/12C$ 646
Tue 27/16:00 a.m.YHZ - ORD
2 stops16h 47mWestJet
Sat 28/25:37 p.m.ORD - YHZ
2 stops30h 04mWestJet
Deal found 22/12C$ 585
Tue 27/11:20 p.m.YHZ - MDW
2 stops22h 45mPorter Airlines
Sat 28/212:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 22/12C$ 643
Tue 27/16:30 a.m.YHZ - ORD
1 stop7h 55mMultiple Airlines
Sat 28/210:35 a.m.ORD - YHZ
2 stops13h 06mMultiple Airlines
Deal found 22/12C$ 723
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 23 December 2025.
Tue 20/111:35 a.m.YHZ - ORD
2 stops25h 47mMultiple Airlines
Deal found 20/12C$ 237
Thu 22/18:20 p.m.YHZ - ORD
2 stops27h 44mMultiple Airlines
Deal found 20/12C$ 244
Mon 19/110:40 p.m.YHZ - ORD
2 stops37h 03mMultiple Airlines
Deal found 20/12C$ 246
Wed 21/18:20 p.m.YHZ - ORD
2 stops28h 16mMultiple Airlines
Deal found 20/12C$ 248
Mon 23/28:45 a.m.YHZ - ORD
1 stop16h 30mMultiple Airlines
Deal found 22/12C$ 251
Thu 5/28:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Deal found 21/12C$ 252
Sat 17/16:40 a.m.YHZ - ORD
2 stops15h 01mMultiple Airlines
Deal found 20/12C$ 257
Fri 23/110:40 p.m.YHZ - ORD
3 stops19h 55mMultiple Airlines
Deal found 20/12C$ 259
Tue 3/311:35 a.m.YHZ - ORD
2 stops14h 12mMultiple Airlines
Deal found 22/12C$ 260
Mon 5/18:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Deal found 20/12C$ 266
Sun 18/11:20 p.m.YHZ - MDW
2 stops12h 42mMultiple Airlines
Deal found 21/12C$ 285
Tue 3/311:35 a.m.YHZ - MDW
2 stops23h 18mMultiple Airlines
Deal found 22/12C$ 329
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 23 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 23 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
7:00 a.m.-3:20 p.m.
2 stops10h 20m
Chicago Midway
Wed 15/4
11:00 a.m.-11:54 p.m.
2 stops10h 54m
C$ 319
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Wed 4/2
1:20 p.m.-11:47 p.m.
2 stops12h 27m
Chicago O'Hare Intl
Wed 11/2
7:20 a.m.-10:50 a.m.
2 stops25h 30m
C$ 414
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Wed 4/2
4:50 p.m.-10:10 a.m.
2 stops19h 20m
Chicago Midway
Wed 11/2
11:00 a.m.-8:10 p.m.
1 stop7h 10m
C$ 505
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 16/1
10:40 p.m.-11:46 p.m.
2 stops27h 06m
Chicago O'Hare Intl
Mon 19/1
5:15 a.m.-10:50 a.m.
2 stops27h 35m
C$ 515
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Sat 10/1
6:40 a.m.-11:50 a.m.
2 stops7h 10m
Chicago Midway
Sat 17/1
12:45 p.m.-8:10 p.m.
1 stop5h 25m
C$ 537
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Fri 3/4
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$ 556
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Tue 27/1
6:00 a.m.-8:47 p.m.
2 stops16h 47m
Chicago O'Hare Intl
Sat 28/2
5:37 p.m.-1:41 a.m.
2 stops30h 04m
C$ 585
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 6/2
10:40 p.m.-9:03 p.m.
2 stops24h 23m
Chicago O'Hare Intl
Fri 13/2
2:20 p.m.-7:28 a.m.
1 stop15h 08m
C$ 585
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$ 595
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Sat 10/1
6:55 a.m.-11:06 a.m.
1 stop6h 11m
Chicago O'Hare Intl
Sat 17/1
10:00 a.m.-7:44 p.m.
2 stops7h 44m
C$ 611
Flights are sorted by cheapest round-trip flights first.
Deals found on 22/12
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 19 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$ 607). 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 23 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 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.
Newark (EWR) is the most affordable 1-stop option, with an average round-trip price of C$ 401.
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 23 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$ 319, Porter Airlines can have you in Chicago from Halifax in 10h 20m. 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$ 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: 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$ 138). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 607). 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 23 December 2025.
Browse through other flights departing from Halifax. Flights are based on user searches made on Cheapflights and were last updated on 23 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 23 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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