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 28/5. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
17 Jan — 24 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 18 December 2025.
Thu 25/121:00 p.m.YHZ - ORD
1 stop7h 53mAir Canada
Thu 1/16:00 a.m.ORD - YHZ
1 stop15h 54mAir Canada
Deal found 17/12C$ 853
Thu 25/126:30 a.m.YHZ - ORD
1 stop8h 03mAmerican Airlines
Thu 1/16:15 a.m.ORD - YHZ
2 stops16h 07mAmerican Airlines
Deal found 17/12C$ 854
Fri 26/1211:20 a.m.YHZ - ORD
1 stop5h 35mAir Canada
Thu 1/16:00 a.m.ORD - YHZ
1 stop15h 54mAir Canada
Deal found 17/12C$ 857
Sat 27/126:00 a.m.YHZ - MDW
2 stops28h 49mWestJet
Fri 2/16:08 p.m.MDW - YHZ
2 stops29h 33mWestJet
Deal found 18/12C$ 875
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Wed 31/1211:00 a.m.MDW - YHZ
2 stops8h 29mPorter Airlines
Deal found 15/12C$ 878
Sat 27/126:00 a.m.YHZ - ORD
2 stops16h 36mWestJet
Fri 2/19:41 a.m.ORD - YHZ
2 stops38h 00mWestJet
Deal found 16/12C$ 922
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 16/12C$ 938
Fri 26/126:00 a.m.YHZ - ORD
2 stops17h 34mWestJet
Thu 1/17:00 a.m.ORD - YHZ
2 stops16h 41mWestJet
Deal found 17/12C$ 941
Fri 26/126:55 a.m.YHZ - ORD
1 stop6h 23mAir Canada
Fri 2/16:00 a.m.ORD - YHZ
1 stop8h 14mAir Canada
Deal found 16/12C$ 988
Fri 26/126:00 a.m.YHZ - ORD
2 stops17h 34mWestJet
Fri 2/19:41 a.m.ORD - YHZ
2 stops38h 00mWestJet
Deal found 17/12C$ 1,000
Fri 26/126:00 a.m.YHZ - MDW
2 stops37h 26mWestJet
Fri 2/16:08 p.m.MDW - YHZ
2 stops29h 33mWestJet
Deal found 18/12C$ 1,003
Fri 26/126:00 a.m.YHZ - MDW
2 stops37h 26mWestJet
Thu 1/16:08 p.m.MDW - YHZ
2 stops29h 33mWestJet
Deal found 18/12C$ 1,026
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 18 December 2025.
Tue 14/47:00 a.m.YHZ - MDW
2 stops10h 20mPorter Airlines
Wed 15/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 17/12C$ 338
Mon 12/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Thu 15/18:43 p.m.ORD - YHZ
2 stops23h 12mMultiple Airlines
Deal found 15/12C$ 467
Wed 21/16:00 a.m.YHZ - MDW
2 stops13h 55mWestJet
Sat 24/19:33 a.m.MDW - YHZ
2 stops14h 08mWestJet
Deal found 16/12C$ 543
Thu 2/48:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Sun 5/411:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 17/12C$ 488
Fri 30/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Mon 2/27:00 a.m.ORD - YHZ
2 stops25h 50mMultiple Airlines
Deal found 15/12C$ 517
Tue 13/16:00 a.m.YHZ - ORD
2 stops29h 41mWestJet
Tue 20/112:15 p.m.ORD - YHZ
2 stops11h 26mWestJet
Deal found 16/12C$ 564
Sat 17/18:45 a.m.YHZ - ORD
1 stop12h 56mMultiple Airlines
Sat 24/17:21 p.m.ORD - YHZ
2 stops28h 20mMultiple Airlines
Deal found 17/12C$ 525
Wed 21/17:05 p.m.YHZ - MDW
2 stops17h 00mPorter Airlines
Sat 24/112:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 16/12C$ 539
Sat 17/16:00 a.m.YHZ - ORD
2 stops14h 58mWestJet
Sat 24/110:35 a.m.ORD - YHZ
2 stops13h 06mWestJet
Deal found 17/12C$ 577
Fri 16/18:45 a.m.YHZ - MDW
2 stops17h 02mMultiple Airlines
Mon 19/111:05 a.m.MDW - YHZ
1 stop7h 05mMultiple Airlines
Deal found 17/12C$ 543
Tue 27/16:00 a.m.YHZ - ORD
2 stops29h 41mWestJet
Thu 19/27:10 a.m.ORD - YHZ
2 stops16h 31mWestJet
Deal found 16/12C$ 601
Fri 16/11:10 p.m.YHZ - ORD
1 stop8h 54mMultiple Airlines
Mon 19/12:20 p.m.ORD - YHZ
1 stop15h 08mMultiple Airlines
Deal found 17/12C$ 558
Last-minute flights from Halifax to Chicago
Discover last-minute flight deals from Halifax to Chicago. Data last updated 18 December 2025 and is based on user searches.
Mon 12/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Thu 15/18:43 p.m.ORD - YHZ
2 stops23h 12mMultiple Airlines
Deal found 15/12C$ 467
Mon 12/18:45 a.m.YHZ - MDW
1 stop16h 24mMultiple Airlines
Thu 15/11:28 p.m.MDW - YHZ
2 stops10h 13mMultiple Airlines
Deal found 15/12C$ 565
Tue 13/14:50 p.m.YHZ - MDW
2 stops19h 15mPorter Airlines
Tue 20/111:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 16/12C$ 548
Tue 13/16:00 a.m.YHZ - MDW
2 stops28h 52mWestJet
Tue 20/19:32 a.m.MDW - YHZ
2 stops14h 09mWestJet
Deal found 16/12C$ 564
Tue 13/16:00 a.m.YHZ - ORD
2 stops29h 41mWestJet
Tue 20/112:15 p.m.ORD - YHZ
2 stops11h 26mWestJet
Deal found 16/12C$ 564
Fri 16/18:45 a.m.YHZ - MDW
2 stops17h 02mMultiple Airlines
Mon 19/111:05 a.m.MDW - YHZ
1 stop7h 05mMultiple Airlines
Deal found 17/12C$ 543
Fri 16/11:10 p.m.YHZ - ORD
1 stop8h 54mMultiple Airlines
Mon 19/12:20 p.m.ORD - YHZ
1 stop15h 08mMultiple Airlines
Deal found 17/12C$ 558
Sat 17/18:45 a.m.YHZ - ORD
1 stop12h 56mMultiple Airlines
Sat 24/17:21 p.m.ORD - YHZ
2 stops28h 20mMultiple Airlines
Deal found 17/12C$ 525
Sat 17/16:00 a.m.YHZ - ORD
2 stops14h 58mWestJet
Sat 24/110:35 a.m.ORD - YHZ
2 stops13h 06mWestJet
Deal found 17/12C$ 577
Wed 21/17:05 p.m.YHZ - MDW
2 stops17h 00mPorter Airlines
Sat 24/112:45 p.m.MDW - YHZ
1 stop5h 25mPorter Airlines
Deal found 16/12C$ 539
Wed 21/16:00 a.m.YHZ - ORD
2 stops12h 57mWestJet
Sat 24/15:35 p.m.ORD - YHZ
2 stops30h 06mWestJet
Deal found 16/12C$ 543
Fri 30/18:45 a.m.YHZ - ORD
1 stop11h 07mMultiple Airlines
Mon 2/27:00 a.m.ORD - YHZ
2 stops25h 50mMultiple Airlines
Deal found 15/12C$ 517
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 18 December 2025.
Thu 28/57:40 a.m.YHZ - ORD
1 stop11h 03mWestJet
Deal found 16/12C$ 231
Mon 19/110:40 p.m.YHZ - ORD
2 stops25h 24mMultiple Airlines
Deal found 17/12C$ 245
Wed 14/16:00 a.m.YHZ - ORD
2 stops17h 03mMultiple Airlines
Deal found 17/12C$ 247
Mon 12/110:40 p.m.YHZ - ORD
2 stops25h 24mMultiple Airlines
Deal found 16/12C$ 249
Tue 17/211:35 a.m.YHZ - ORD
2 stops25h 47mMultiple Airlines
Deal found 17/12C$ 252
Wed 18/28:20 p.m.YHZ - ORD
2 stops29h 04mMultiple Airlines
Deal found 16/12C$ 254
Thu 15/16:40 a.m.YHZ - ORD
2 stops13h 12mMultiple Airlines
Deal found 16/12C$ 255
Sun 18/16:00 a.m.YHZ - ORD
2 stops53h 43mMultiple Airlines
Deal found 17/12C$ 263
Fri 30/18:45 a.m.YHZ - MDW
1 stop13h 07mMultiple Airlines
Deal found 16/12C$ 296
Mon 2/31:20 p.m.YHZ - MDW
3 stops31h 47mMultiple Airlines
Deal found 17/12C$ 311
Fri 30/16:00 a.m.YHZ - MDW
2 stops13h 55mWestJet
Deal found 16/12C$ 338
Wed 24/129:00 a.m.YHZ - MDW
1 stop14h 58mMultiple Airlines
Deal found 16/12C$ 360
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 18 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 18 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.-8:05 p.m.
1 stop7h 05m
C$ 338
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Mon 12/1
8:45 a.m.-5:52 p.m.
1 stop11h 07m
Chicago O'Hare Intl
Thu 15/1
8:43 p.m.-9:55 p.m.
2 stops23h 12m
C$ 467
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Thu 2/4
8:25 a.m.-3:20 p.m.
2 stops8h 55m
Chicago Midway
Sun 5/4
11:00 a.m.-8:05 p.m.
1 stop7h 05m
C$ 488
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 30/1
8:45 a.m.-5:52 p.m.
1 stop11h 07m
Chicago O'Hare Intl
Mon 2/2
7:00 a.m.-10:50 a.m.
2 stops25h 50m
C$ 517
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Sat 17/1
8:45 a.m.-7:41 p.m.
1 stop12h 56m
Chicago O'Hare Intl
Sat 24/1
7:21 p.m.-1:41 a.m.
2 stops28h 20m
C$ 525
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Wed 21/1
7:05 p.m.-10:05 a.m.
2 stops17h 00m
Chicago Midway
Sat 24/1
12:45 p.m.-8:10 p.m.
1 stop5h 25m
C$ 539
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Wed 21/1
6:00 a.m.-5:55 p.m.
2 stops13h 55m
Chicago Midway
Sat 24/1
9:33 a.m.-1:41 a.m.
2 stops14h 08m
C$ 543
HalifaxChicago
YHZ - MDW
YHZMDW
Halifax Intl
Fri 16/1
8:45 a.m.-11:47 p.m.
2 stops17h 02m
Chicago Midway
Mon 19/1
11:05 a.m.-8:10 p.m.
1 stop7h 05m
C$ 543
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Fri 16/1
1:10 p.m.-8:04 p.m.
1 stop8h 54m
Chicago O'Hare Intl
Mon 19/1
2:20 p.m.-7:28 a.m.
1 stop15h 08m
C$ 558
HalifaxChicago
YHZ - ORD
YHZORD
Halifax Intl
Tue 13/1
6:00 a.m.-9:41 a.m.
2 stops29h 41m
Chicago O'Hare Intl
Tue 20/1
12:15 p.m.-1:41 a.m.
2 stops11h 26m
C$ 564
Flights are sorted by cheapest round-trip flights first.
Deals found on 16/12
Showing 1-10 of 25 results
1
2
3
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 12 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$ 608). 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 18 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.
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 49% 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$ 402.
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 18 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$ 338, 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$ 608). 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 18 December 2025.
Browse through other flights departing from Halifax. Flights are based on user searches made on Cheapflights and were last updated on 18 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 18 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.
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
We value your privacy
Cheapflights and its partners wish to use cookies or similar technologies to store and/or access information on and about your device and process personal data such as your IP address, device identifiers etc., in order to improve your experience on the site, to analyze navigation, to offer and measure personalized advertising, and to facilitate sharing on social networks. We also allow the use of third-party cookies (including those from our advertising partners) on our sites.
By clicking 'Accept', you consent to your data being processed by 0 vendors on this web site for the purposes described in this notice. You can review the vendors and their individual processing purposes on the .
To review individual processing purposes and cookie categories, please click ’Select individual purposes’. You can review and update your choices anytime by clicking the ’Privacy Preferences’ link in the page side navigation.