$180+ Cheap flights from Halifax (YHZ) to Chicago (CHI)
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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Sep 11 — Sep 181
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Halifax to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Halifax to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Halifax to ChicagoExplore 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 August 12, 2026.
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 August 12, 2026.
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
1 stop5h 50m
Wed 9/233:40 pm -
1 stop6h 55m
Deal found 8/7![Air Canada logo]()
$311
This Air Canada deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
1 stop5h 50m
Wed 9/303:40 pm -
1 stop6h 55m
Deal found 8/10![Air Canada logo]()
$313
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
1 stop5h 50m
Sun 9/203:40 pm -
1 stop6h 55m
Deal found 8/9![Air Canada logo]()
$315
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop5h 50m
Tue 9/293:40 pm -
1 stop6h 55m
Deal found 8/7![Air Canada logo]()
$318
This FlightHub deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
2 stops9h 35m
Tue 10/611:45 am -
2 stops9h 59m
Deal found 8/9![Porter Airlines logo]()
$323
This Air Canada deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:15 am -
1 stop5h 45m
Mon 9/143:40 pm -
1 stop6h 55m
Deal found 8/10![Air Canada logo]()
$323
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:25 am -
1 stop5h 50m
Sat 9/263:40 pm -
1 stop6h 55m
Deal found 8/7![Air Canada logo]()
$324
This Air Canada deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:45 am -
1 stop6h 32m
Tue 10/203:40 pm -
1 stop6h 15m
Deal found 8/10![Air Canada logo]()
$326
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop5h 50m
Mon 10/58:45 am -
1 stop5h 17m
Deal found 8/9![Air Canada logo]()
$328
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:05 am -
1 stop7h 02m
Mon 11/304:30 pm -
1 stop6h 18m
Deal found 8/7![Air Canada logo]()
$329
This Justfly.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:00 am -
2 stops9h 35m
Sat 10/311:45 am -
2 stops9h 59m
Deal found 8/10![Porter Airlines logo]()
$331
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:25 am -
1 stop5h 54m
Thu 9/1011:05 am -
1 stop6h 05m
Deal found 8/7![Air Canada logo]()
$331
Best flights from Halifax to ChicagoDiscover 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 August 12, 2026.
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 August 12, 2026.
This Air Canada deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 am -
1 stop5h 50m
Sat 9/128:45 am -
1 stop5h 17m
Deal found 8/11![Air Canada logo]()
$337
This FlightHub deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:00 am -
2 stops8h 35m
Tue 9/111:45 am -
2 stops9h 59m
Deal found 8/7![Porter Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am -
1 stop7h 59m
Mon 9/145:00 am -
1 stop7h 03m
Deal found 8/6![United Airlines logo]()
$380
This Mytrip deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am -
2 stops9h 35m
Sat 9/1911:45 am -
1 stop7h 40m
Deal found 8/10![Multiple Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:33 pm -
2 stops8h 57m
Tue 9/111:30 am -
1 stop9h 48m
Deal found 8/7![Delta logo]()
$399
This Porter Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:25 am -
2 stops9h 10m
Fri 10/23:20 pm -
2 stops6h 24m
Deal found 8/10![Porter Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:30 am -
2 stops12h 21m
Thu 9/106:00 am -
1 stop5h 27m
Deal found 8/7![Delta logo]()
$418
This United Airlines deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:10 pm -
2 stops10h 18m
Sun 9/135:00 am -
1 stop9h 00m
Deal found 8/8![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:30 pm -
2 stops10h 27m
Sat 9/58:05 am -
2 stops13h 08m
Deal found 8/8![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:30 pm -
2 stops10h 29m
Wed 9/308:05 am -
2 stops11h 05m
Deal found 8/8![Delta logo]()
$433
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:30 pm -
1 stop5h 03m
Wed 9/301:19 pm -
1 stop5h 51m
Deal found 8/10![Delta logo]()
$434
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:30 pm -
1 stop7h 00m
Tue 9/296:40 am -
2 stops12h 30m
Deal found 8/7![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:30 pm -
2 stops9h 14m
Sat 9/266:05 am -
2 stops13h 05m
Deal found 8/7![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:30 pm -
2 stops10h 29m
Sat 9/266:40 am -
2 stops12h 30m
Deal found 8/7![Delta logo]()
$440
This Delta deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/73:30 pm -
1 stop5h 03m
Mon 9/141:19 pm -
1 stop5h 51m
Deal found 8/9![Delta logo]()
$442
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:30 pm -
2 stops10h 29m
Sat 9/192:00 pm -
1 stop5h 10m
Deal found 8/10![Delta logo]()
$442
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:30 pm -
2 stops9h 14m
Sat 9/129:29 am -
1 stop9h 41m
Deal found 8/11![Delta logo]()
$449
Last-minute flights from Halifax to ChicagoDiscover last-minute flight deals from Halifax to Chicago. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Halifax to Chicago. Data last updated August 12, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:25 am -
1 stop5h 54m
Thu 9/1011:05 am -
1 stop6h 05m
Deal found 8/7![Air Canada logo]()
$331
This Air Canada deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:15 am -
1 stop5h 45m
Mon 9/143:40 pm -
1 stop6h 55m
Deal found 8/10![Air Canada logo]()
$323
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:25 am -
1 stop5h 50m
Sat 9/193:40 pm -
1 stop6h 55m
Deal found 8/9![Air Canada logo]()
$332
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
1 stop5h 50m
Wed 9/233:40 pm -
1 stop6h 55m
Deal found 8/7![Air Canada logo]()
$311
This Air Canada deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
1 stop5h 50m
Wed 9/303:40 pm -
1 stop6h 55m
Deal found 8/10![Air Canada logo]()
$313
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:25 am -
1 stop5h 50m
Sun 9/203:40 pm -
1 stop6h 55m
Deal found 8/9![Air Canada logo]()
$315
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:25 am -
1 stop5h 50m
Sat 9/263:40 pm -
1 stop6h 55m
Deal found 8/7![Air Canada logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:45 am -
1 stop25h 15m
Sat 9/263:20 pm -
1 stop17h 25m
Deal found 8/7![Multiple Airlines logo]()
$333
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop5h 50m
Tue 9/293:40 pm -
1 stop6h 55m
Deal found 8/7![Air Canada logo]()
$318
This FlightHub deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
2 stops9h 35m
Tue 10/611:45 am -
2 stops9h 59m
Deal found 8/9![Porter Airlines logo]()
$323
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:25 am -
1 stop5h 50m
Mon 10/58:45 am -
1 stop5h 17m
Deal found 8/9![Air Canada logo]()
$328
This Justfly.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:00 am -
2 stops9h 35m
Sat 10/311:45 am -
2 stops9h 59m
Deal found 8/10![Porter Airlines logo]()
$331
One-way flights from Halifax to ChicagoSearch for one-way flight options from Halifax to Chicago. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
Search for one-way flight options from Halifax to Chicago. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:45 am -
1 stop6h 32m
Deal found 8/7![Air Canada logo]()
$180
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:25 am -
1 stop5h 50m
Deal found 8/9![Air Canada logo]()
$181
This Air Canada deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:25 am -
1 stop5h 51m
Deal found 8/9![Air Canada logo]()
$183
This Air Canada deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1011:30 am -
1 stop5h 22m
Deal found 8/11![Air Canada logo]()
$185
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/62:30 pm -
1 stop7h 35m
Deal found 8/7![Air Canada logo]()
$187
This Delta deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:17 pm -
1 stop8h 14m
Deal found 8/7![Delta logo]()
$188
This Air Canada deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:15 am -
1 stop5h 45m
Deal found 8/7![Air Canada logo]()
$191
This Air Canada deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:25 am -
1 stop5h 51m
Deal found 8/11![Air Canada logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:25 pm -
2 stops23h 10m
Deal found 8/11![Porter Airlines logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:25 am -
2 stops9h 10m
Deal found 8/10![Porter Airlines logo]()
$198
This Justfly.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:00 am -
2 stops9h 35m
Deal found 8/10![Porter Airlines logo]()
$199
This Trip.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:00 am -
1 stop8h 35m
Deal found 8/9![Porter Airlines logo]()
$201
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 August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (Air Canada) |
One-way from | $180 (Air Canada) |
Popular in | January |
Cheapest in | December |
Average price | $343 |
Good round-trip deal | $361 or less |
Good one-way deal | $299 or less |
Cheapflights Fare Finder
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 2,558,603 searches. Data last updated August 12, 2026.
Use the filters below to find and compare flights from Halifax to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HalifaxChicago
YHZ Halifax Intl - ORD Chicago O'Hare Intl
YHZORD
Halifax Intl
Wed 9/9
6:25 am-10:15 am
1 stop5h 50m
Chicago O'Hare Intl
Sat 9/12
8:45 am-4:02 pm
1 stop5h 17m
$337
HalifaxChicago
YHZ Halifax Intl - MDW Chicago Midway
YHZMDW
Halifax Intl
Fri 8/28
8:00 am-2:35 pm
2 stops8h 35m
Chicago Midway
Tue 9/1
11:45 am-11:44 pm
2 stops9h 59m
$360
HalifaxChicago
YHZ Halifax Intl - ORD Chicago O'Hare Intl
YHZORD
Halifax Intl
Thu 9/10
7:00 am-12:59 pm
1 stop7h 59m
Chicago O'Hare Intl
Mon 9/14
5:00 am-2:03 pm
1 stop7h 03m
$380
HalifaxChicago
YHZ Halifax Intl - MDW Chicago Midway
YHZMDW
Halifax Intl
Sat 9/12
7:00 am-2:35 pm
2 stops9h 35m
Chicago Midway
Sat 9/19
11:45 am-9:25 pm
1 stop7h 40m
$391
HalifaxChicago
YHZ Halifax Intl - ORD Chicago O'Hare Intl
YHZORD
Halifax Intl
Fri 8/28
1:33 pm-8:30 pm
2 stops8h 57m
Chicago O'Hare Intl
Tue 9/1
11:30 am-11:18 pm
1 stop9h 48m
$399
HalifaxChicago
YHZ Halifax Intl - MDW Chicago Midway
YHZMDW
Halifax Intl
Fri 9/25
7:25 am-2:35 pm
2 stops9h 10m
Chicago Midway
Fri 10/2
3:20 pm-11:44 pm
2 stops6h 24m
$406
HalifaxChicago
YHZ Halifax Intl - ORD Chicago O'Hare Intl
YHZORD
Halifax Intl
Sun 9/6
6:30 am-4:51 pm
2 stops12h 21m
Chicago O'Hare Intl
Thu 9/10
6:00 am-1:27 pm
1 stop5h 27m
$418
HalifaxChicago
YHZ Halifax Intl - ORD Chicago O'Hare Intl
YHZORD
Halifax Intl
Sat 8/29
3:30 pm-11:57 pm
2 stops10h 27m
Chicago O'Hare Intl
Sat 9/5
8:05 am-11:13 pm
2 stops13h 08m
$419
HalifaxChicago
YHZ Halifax Intl - ORD Chicago O'Hare Intl
YHZORD
Halifax Intl
Tue 9/22
3:30 pm-11:59 pm
2 stops10h 29m
Chicago O'Hare Intl
Wed 9/30
8:05 am-9:10 pm
2 stops11h 05m
$433
Quickest round-trip
HalifaxChicago
YHZ Halifax Intl - MDW Chicago Midway
YHZMDW
Halifax Intl
Wed 9/16
3:30 pm-6:33 pm
1 stop5h 03m
Chicago Midway
Wed 9/30
1:19 pm-9:10 pm
1 stop5h 51m
$434
Showing 1-10 of 35 resultsSorted by cheapest first
Compare providers for flights from Halifax to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Halifax to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Halifax-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Halifax-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Halifax-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Halifax-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Halifax-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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.
YHZ-CHI
YHZ-ORD
YHZ-MDW
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
YHZ-CHI
YHZ-ORD
YHZ-MDW
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 $266). Flying from Halifax to Chicago in January is currently the most expensive (average of $690). 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 August 12, 2026.
When flying from Halifax to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Halifax to Chicago?
Airfare is below average for this route at the moment.
Halifax to Chicago flights typically cost between $313 and $409 in September.The cheapest round-trip price found within the last 5 days was $311 on Air Canada (Sep 16-Sep 23).
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Halifax
Popular flights
Alternative routes for Halifax to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 12, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Halifax to Chicago by cabin class
Find flights from Halifax to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Halifax and Chicago flights
Browse other Halifax and Chicago flight options. Last updated on August 12, 2026.
Other flights from Halifax
Browse through other flights departing from Halifax. Flights are based on user searches made on Cheapflights and were last updated on August 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Halifax to Chicago
Discover the top airline 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 2,558,603 searches. Data last updated August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$182 | Average$479 | FlexibilityNo cancel fee | On-time67% |