Cheap Flights from Halifax, NS to Chicago, IL from $184

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On Cheapflightsplus.com you will find 1 direct and 418 connecting flights from Halifax to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $184, book and save on cheap plane tickets and last minute offers. Also check out YHZ-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Halifax to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $184 (one-way), $316 (round-trip).

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Best Flights from Halifax to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Halifax to Chicago with the lowest price of $184. The fastest direct flight takes 3h 45m and the fastest connecting – 5h 26m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $571 Find flight	17:00 Halifax Halifax Int.	18:45 Chicago O'Hare International	3h 45m	United Airlines	UA5934
from $184 Find flight	18:30 Halifax Halifax Int.	08:19+1 день Chicago Midway	15h 49m layover 11h 30m - Toronto	WestJet	WS281 PD2387
from $184 Find flight	15:20 Halifax Halifax Int.	08:19+1 день Chicago Midway	18h 59m layover 14h 40m - Toronto	WestJet	WS277 PD2387
from $184 Find flight	08:30 Halifax Halifax Int.	08:19+1 день Chicago Midway	25h 49m layover 21h 31m - Toronto	WestJet	WS249 PD2387
from $185 Find flight	08:30 Halifax Halifax Int.	16:24 Chicago Midway	9h 54m layover 5h 36m - Toronto	WestJet	WS249 PD2393
from $205 Find flight	18:45 Halifax Halifax Int.	08:19+1 день Chicago Midway	15h 34m layover 11h 19m - Toronto	Porter Airlines	PD206 PD2387
from $205 Find flight	17:20 Halifax Halifax Int.	08:19+1 день Chicago Midway	16h 59m layover 12h 21m - Toronto	Porter Airlines	PD2292 PD2387
from $205 Find flight	08:25 Halifax Halifax Int.	08:19+1 день Chicago Midway	25h 54m layover 21h 40m - Toronto	Porter Airlines	PD204 PD2387
from $205 Find flight	06:30 Halifax Halifax Int.	08:19+1 день Chicago Midway	27h 49m layover 23h 34m - Toronto	Porter Airlines	PD200 PD2387
from $206 Find flight	08:25 Halifax Halifax Int.	16:24 Chicago Midway	9h 59m layover 5h 45m - Toronto	Porter Airlines	PD204 PD2393
from $206 Find flight	06:30 Halifax Halifax Int.	16:24 Chicago Midway	11h 54m layover 7h 39m - Toronto	Porter Airlines	PD200 PD2393
from $218 Find flight	11:05 Halifax Halifax Int.	08:19+1 день Chicago Midway	23h 14m layover 18h 59m - Toronto	Porter Airlines	PD202 PD2387
from $198 Find flight	09:15 Halifax Halifax Int.	08:19+1 день Chicago Midway	25h 4m layover 2h 58m - Montreal 16h 55m - Toronto	Porter Airlines	PD2324 PD2466 PD2387
from $199 Find flight	06:45 Halifax Halifax Int.	16:24 Chicago Midway	11h 39m layover 0h 41m - Ottawa 5h 57m - Toronto	Porter Airlines	PD2230 PD2210 PD2393
from $203 Find flight	06:45 Halifax Halifax Int.	16:24 Chicago Midway	11h 39m layover 3h 6m - Ottawa 3h 32m - Toronto	Porter Airlines	PD2230 PD2216 PD2393
from $228 Find flight	12:00 Halifax Halifax Int.	23:10 Chicago O'Hare International	13h 10m layover 3h 19m - Ottawa 3h 53m - Newark	Porter Airlines	PD242 PD2339 NK329

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 12, 2025

Flight Schedule Halifax (Nova Scotia) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Halifax to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
17:00 — 18:45	17:00 — 18:45 UA5934 United Airlines Halifax — Chicago	3h 45m	Find flight from$571
05:25 — 09:08	05:00 — 06:47 UA8265 United Airlines Halifax — Toronto 1h 21m stop 08:00 — 08:57 UA8533 United Airlines Toronto — Chicago	5h 43m including layover	Find flight from$242
05:25 — 10:53	05:25 — 06:54 UA8265 United Airlines Halifax — Toronto 3h 6m stop 10:00 — 10:53 UA8278 United Airlines Toronto — Chicago	7h 28m including layover	Find flight from$242
07:00 — 11:49	07:00 — 08:22 UA3446 United Airlines Halifax — Newark 1h 48m stop 10:10 — 11:49 UA1525 United Airlines Newark — Chicago	6h 49m including layover	Find flight from$242
07:00 — 13:07	07:00 — 08:22 UA3446 United Airlines Halifax — Newark 3h 7m stop 11:29 — 13:07 UA1875 United Airlines Newark — Chicago	8h 7m including layover	Find flight from$242
08:30 — 08:19 +1 day	08:30 — 09:59 WS249 WestJet Halifax — Toronto 21h 31m stop 07:55 — 08:45 PD2387 Porter Airlines Toronto — Chicago	25h 49m including layover	Find flight from$184
08:30 — 16:24	08:30 — 09:59 WS249 WestJet Halifax — Toronto 5h 36m stop 15:35 — 16:24 PD2393 Porter Airlines Toronto — Chicago	9h 54m including layover	Find flight from$185
10:25 — 16:35	10:25 — 11:54 UA6624 United Airlines Halifax — Newark 3h 1m stop 14:55 — 16:35 UA2009 United Airlines Newark — Chicago	8h 10m including layover	Find flight from$242
10:25 — 21:26	10:25 — 11:56 UA6624 United Airlines Halifax — Newark 7h 51m stop 19:46 — 21:28 UA546 United Airlines Newark — Chicago	13h 1m including layover	Find flight from$242
11:05 — 08:19 +1 day	11:05 — 12:31 PD202 Porter Airlines Halifax — Toronto 18h 59m stop 07:55 — 08:45 PD2387 Porter Airlines Toronto — Chicago	23h 14m including layover	Find flight from$218
11:45 — 08:19 +1 day	11:45 — 13:10 F8657 Freedom Airlines Halifax — Toronto 18h 20m stop 07:55 — 08:45 PD2387 Porter Airlines Toronto — Chicago	22h 34m including layover	Find flight from$231
13:30 — 19:29	13:30 — 14:57 UA8159 United Airlines Halifax — Toronto 3h 40m stop 18:35 — 19:29 UA8293 United Airlines Toronto — Chicago	7h 59m including layover	Find flight from$242
15:20 — 08:19 +1 day	15:20 — 16:51 WS277 WestJet Halifax — Toronto 14h 40m stop 07:55 — 08:45 PD2387 Porter Airlines Toronto — Chicago	18h 59m including layover	Find flight from$184
15:20 — 16:24 +1 day	15:20 — 16:50 WS277 WestJet Halifax — Toronto 22h 45m stop 15:35 — 16:24 PD2393 Porter Airlines Toronto — Chicago	27h 4m including layover	Find flight from$208
17:20 — 08:19 +1 day	17:15 — 19:04 PD2292 Porter Airlines Halifax — Toronto 12h 21m stop 07:55 — 08:45 PD2387 Porter Airlines Toronto — Chicago	16h 59m including layover	Find flight from$205
17:20 — 16:24 +1 day	17:15 — 19:04 PD2292 Porter Airlines Halifax — Toronto 20h 26m stop 15:35 — 16:24 PD2393 Porter Airlines Toronto — Chicago	25h 4m including layover	Find flight from$242
18:30 — 08:19 +1 day	18:30 — 20:01 WS281 WestJet Halifax — Toronto 11h 30m stop 07:55 — 08:45 PD2387 Porter Airlines Toronto — Chicago	15h 49m including layover	Find flight from$184
18:45 — 08:19 +1 day	14:40 — 16:14 PD206 Porter Airlines Halifax — Toronto 11h 19m stop 09:30 — 10:20 PD2387 Porter Airlines Toronto — Chicago	15h 34m including layover	Find flight from$205
23:00 — 08:19 +1 day	11:15 — 12:55 F8651 Freedom Airlines Halifax — Toronto 7h 5m stop 09:30 — 10:20 PD2387 Porter Airlines Toronto — Chicago	11h 19m including layover	Find flight from$234
23:00 — 16:24 +1 day	23:00 — 00:25 F8651 Freedom Airlines Halifax — Toronto 15h 10m stop 15:35 — 16:24 PD2393 Porter Airlines Toronto — Chicago	19h 24m including layover	Find flight from$234
06:45 — 16:24	06:30 — 07:48 PD2230 Porter Airlines Halifax — Ottawa 41m stop 09:40 — 10:48 PD2210 Porter Airlines Ottawa — Toronto 5h 57m stop 15:50 — 16:40 PD2393 Porter Airlines Toronto — Chicago	11h 39m including layover	Find flight from$199
06:45 — 16:24	06:45 — 07:54 PD2230 Porter Airlines Halifax — Ottawa 3h 6m stop 11:00 — 12:02 PD2216 Porter Airlines Ottawa — Toronto 3h 32m stop 15:35 — 16:24 PD2393 Porter Airlines Toronto — Chicago	11h 39m including layover	Find flight from$203
09:15 — 08:19 +1 day	09:15 — 10:12 PD2324 Porter Airlines Halifax — Montreal 2h 58m stop 13:10 — 14:32 PD2466 Porter Airlines Montreal — Toronto 16h 55m stop 07:55 — 08:45 PD2387 Porter Airlines Toronto — Chicago	25h 4m including layover	Find flight from$198
09:15 — 16:24	08:15 — 09:24 PD2324 Porter Airlines Halifax — Montreal 2h 58m stop 11:50 — 13:15 PD2466 Porter Airlines Montreal — Toronto 1h stop 15:50 — 16:40 PD2393 Porter Airlines Toronto — Chicago	9h 9m including layover	Find flight from$203
12:00 — 18:43 +1 day	12:00 — 12:51 PD242 Porter Airlines Halifax — Ottawa 3h 34m stop 16:25 — 19:41 PD505 Porter Airlines Ottawa — Orlando 20h 52m stop 16:33 — 18:43 NK506 Spirit Airlines Orlando — Chicago	32h 43m including layover	Find flight from$199
12:00 — 19:58 +1 day	12:00 — 12:51 PD242 Porter Airlines Halifax — Ottawa 3h 34m stop 16:25 — 19:41 PD505 Porter Airlines Ottawa — Orlando 22h 5m stop 17:46 — 19:58 NK1109 Spirit Airlines Orlando — Chicago	33h 58m including layover	Find flight from$218
19:55 — 20:40 +1 day	19:55 — 20:52 TS7338 Air Transat Halifax — Montreal 9h 53m stop 06:45 — 10:20 TS844 Air Transat Montreal — Miami 8h stop 18:20 — 20:40 NK3 Spirit Airlines Miami — Chicago	26h 45m including layover	Find flight from$246

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on July 12, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Halifax to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Halifax and Chicago is 1970 miles. Time difference between the cities is 2h. Airplanes depart 05:05 to 23:00 from 3 Halifax airports and arrive 05:05 to 23:00 to 7 Chicago airports. Average flight time is 3h 45m.

The fastest flight 3h 45m
Average flight time 3h 45m
The earliest flight 05:05
The latest flight 23:00
Distance 1225 ml

The cheapest months to travel to Chicago are october (from 184 $), september (from 184 $), december (from 202 $).

The most expensive months are february (from 359 $), november (from 352 $), august (from 222 $).

What is the lowest airfare Halifax to Chicago?

The cheapest plane ticket found by our users is $184. This airfare is for economy class on one-way WS249 flight by WestJet for October 7, 2025 which leaves Halifax Int. in Halifax at 08:30 am and arrives at Chicago Midway at 08:19.

Economy class

$184

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Business class

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First class

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Popular Airlines on the Route

The flight Halifax — Chicago is served by 6 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Air Canada - 14 departures per week at the price of from $ 401 . And the most expensive tickets are offered by Freedom Airlines airline - from $ 1077.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA5934 by United Airlines takes 3h 45m and the cheapest is WS249 by WestJet for $571.

UA - United Airlines

from $571

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Connecting Flights

There are 418 flights with layovers on the route. The fastest connecting flight is AC663 by Air Canada takes 5h 26m and the cheapest is WS249 by WestJet for $184.

F8 - Freedom Airlines

from $231

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AC - Air Canada

from $401

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PD - Porter Airlines

from $198

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WS - WestJet

from $184

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UA - United Airlines

from $242

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TS - Air Transat

from $246

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Airports

You can fly from Halifax to Chicago from 3 airports (Dwtown Waterfront H/P, Halifax Int., Shearwater).

Halifax airports

Dwtown Waterfront H/P-YWF

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Halifax Int.-YHZ

from $184
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Shearwater-YAW

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from Halifax by 6 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top International Destinations from Halifax

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Halifax — New York

from $56

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Halifax — Orlando

from $59

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Halifax — Las Vegas

from $55

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Halifax — Tampa

from $65

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Halifax — Miami

from $66

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Halifax — Nashville

from $70

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Halifax — Chicago

from $56

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Halifax — Los Angeles

from $79

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Halifax — Philadelphia

from $64

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Halifax — Houston

from $69

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
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That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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