Cheap Flights from Halifax, NS to Chicago, IL from $166

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On Cheapflightsplus.com you will find 331 connecting flights from Halifax to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $166, 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: $166 (one-way), $285 (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 $166. Take a look at the list of flights with layovers from Halifax to Chicago from $166. There’re no direct flights. The fastest connecting flight – 5h 20m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $166 Find flight	08:30 Halifax Halifax Int.	12:00 Chicago Midway	5h 30m layover 0h 40m - Toronto	Porter Airlines	PD2280 PD2387
from $195 Find flight	06:25 Halifax Halifax Int.	12:00 Chicago Midway	7h 35m layover 3h 11m - Toronto	Porter Airlines	PD200 PD2387
from $208 Find flight	05:00 Halifax Halifax Int.	08:57 Chicago O'Hare International	5h 57m layover 1h 13m - Toronto	United Airlines	UA8265 UA8533
from $211 Find flight	07:10 Halifax Halifax Int.	12:09 Chicago O'Hare International	6h 59m layover 2h 9m - Toronto	United Airlines	UA8267 UA3556
from $211 Find flight	12:20 Halifax Halifax Int.	18:39 Chicago O'Hare International	8h 19m layover 3h 36m - Toronto	United Airlines	UA8271 UA3542
from $211 Find flight	15:15 Halifax Halifax Int.	22:57 Chicago O'Hare International	9h 42m layover 4h 22m - Newark	United Airlines	UA3681 UA1308
from $211 Find flight	10:30 Halifax Halifax Int.	22:57 Chicago O'Hare International	14h 27m layover 9h 7m - Newark	United Airlines	UA6624 UA1308
from $235 Find flight	16:35 Halifax Halifax Int.	11:40+1 день Chicago Midway	21h 5m layover 13h 53m - Tampa	Porter Airlines	PD561 F91185
from $263 Find flight	16:35 Halifax Halifax Int.	09:38+1 день Chicago O'Hare International	19h 3m layover 11h 35m - Tampa	Porter Airlines	PD561 NK1066
from $169 Find flight	06:30 Halifax Halifax Int.	12:00 Chicago Midway	7h 30m layover 0h 47m - Ottawa 1h 27m - Toronto	Porter Airlines	PD2230 PD2206 PD2387
from $215 Find flight	05:00 Halifax Halifax Int.	18:34 Chicago O'Hare International	15h 34m layover 1h 23m - Toronto 7h 34m - Washington D.C.	United Airlines	UA8265 UA8266 UA2497
from $215 Find flight	07:20 Halifax Halifax Int.	23:20 Chicago O'Hare International	18h 0m layover 3h 14m - Toronto 8h 25m - Washington D.C.	United Airlines	UA8267 UA8670 UA1738
from $247 Find flight	16:55 Halifax Halifax Int.	11:48+2 дня Chicago Midway	44h 53m layover 23h 17m - Orlando 8h 17m - Las Vegas	WestJet	WS1040 F91875 F92330
from $260 Find flight	12:20 Halifax Halifax Int.	09:34+1 день Chicago O'Hare International	23h 14m layover 5h 46m - Toronto 11h 1m - Washington D.C.	United Airlines	UA8271 UA3466 UA599
from $260 Find flight	11:20 Halifax Halifax Int.	09:34+1 день Chicago O'Hare International	24h 14m layover 6h 46m - Toronto 11h 1m - Washington D.C.	United Airlines	UA8263 UA3466 UA599
from $266 Find flight	11:20 Halifax Halifax Int.	00:20+1 день Chicago Midway	15h 0m layover 4h 51m - Orlando 1h 3m - Philadelphia	Porter Airlines	PD559 F94170 F94367

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 09, 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
05:00 — 08:57	05:00 — 06:47 UA8265 United Airlines Halifax — Toronto 1h 13m stop 08:00 — 08:57 UA8533 United Airlines Toronto — Chicago	5h 57m including layover	Find flight from$208
05:00 — 10:04	05:00 — 06:47 UA8265 United Airlines Halifax — Toronto 2h 13m stop 09:00 — 10:05 UA1538 United Airlines Toronto — Chicago	7h 4m including layover	Find flight from$208
06:00 — 12:10	06:00 — 07:43 WS243 WestJet Halifax — Toronto 3h 40m stop 11:20 — 12:10 PD2387 Porter Airlines Toronto — Chicago	8h 10m including layover	Find flight from$293
06:25 — 12:00	06:25 — 07:59 PD200 Porter Airlines Halifax — Toronto 3h 11m stop 11:10 — 12:00 PD2387 Porter Airlines Toronto — Chicago	7h 35m including layover	Find flight from$195
07:10 — 12:09	07:10 — 08:51 UA8267 United Airlines Halifax — Toronto 2h 9m stop 11:00 — 12:13 UA3556 United Airlines Toronto — Chicago	6h 59m including layover	Find flight from$211
07:20 — 11:59	07:20 — 09:01 UA8267 United Airlines Halifax — Toronto 1h 59m stop 11:00 — 11:59 UA1063 United Airlines Toronto — Chicago	6h 39m including layover	Find flight from$381
08:30 — 12:00	08:40 — 10:40 PD2280 Porter Airlines Halifax — Toronto 40m stop 09:30 — 10:20 PD2387 Porter Airlines Toronto — Chicago	5h 30m including layover	Find flight from$166
08:45 — 16:40	08:40 — 10:40 PD2280 Porter Airlines Halifax — Toronto 5h 5m stop 15:50 — 16:40 PD2393 Porter Airlines Toronto — Chicago	9h 55m including layover	Find flight from$196
10:30 — 22:57	10:30 — 12:18 UA6624 United Airlines Halifax — Newark 9h 7m stop 21:25 — 22:57 UA1308 United Airlines Newark — Chicago	14h 27m including layover	Find flight from$211
10:30 — 16:26	10:30 — 12:18 UA6624 United Airlines Halifax — Newark 2h 27m stop 14:45 — 16:26 UA276 United Airlines Newark — Chicago	7h 56m including layover	Find flight from$383
11:20 — 18:50	11:20 — 14:30 PD559 Porter Airlines Halifax — Orlando 2h 16m stop 16:46 — 18:50 NK1147 Spirit Airlines Orlando — Chicago	9h 30m including layover	Find flight from$305
11:20 — 20:58	11:20 — 14:30 PD559 Porter Airlines Halifax — Orlando 4h 24m stop 18:54 — 20:58 NK1842 Spirit Airlines Orlando — Chicago	11h 38m including layover	Find flight from$305
12:20 — 18:39	12:20 — 13:54 UA8271 United Airlines Halifax — Toronto 3h 36m stop 17:30 — 18:43 UA3542 United Airlines Toronto — Chicago	8h 19m including layover	Find flight from$211
12:20 — 19:32	12:20 — 13:54 AC609 Air Canada Halifax — Toronto 4h 41m stop 18:35 — 19:32 AC509 Air Canada Toronto — Chicago	9h 12m including layover	Find flight from$461
13:10 — 18:37	13:10 — 14:44 UA8159 United Airlines Halifax — Toronto 2h 46m stop 17:30 — 18:37 UA3608 United Airlines Toronto — Chicago	7h 27m including layover	Find flight from$427
13:10 — 19:32	13:10 — 14:44 UA8159 United Airlines Halifax — Toronto 3h 51m stop 18:35 — 19:32 UA8293 United Airlines Toronto — Chicago	8h 22m including layover	Find flight from$427
14:40 — 10:20 +1 day	14:40 — 16:14 PD206 Porter Airlines Halifax — Toronto 17h 16m stop 09:30 — 10:20 PD2387 Porter Airlines Toronto — Chicago	21h 40m including layover	Find flight from$382
14:40 — 16:40 +1 day	14:40 — 16:14 PD206 Porter Airlines Halifax — Toronto 23h 36m stop 15:50 — 16:40 PD2393 Porter Airlines Toronto — Chicago	28h including layover	Find flight from$382
15:15 — 22:57	15:15 — 16:53 UA3681 United Airlines Halifax — Newark 4h 22m stop 21:29 — 23:00 UA1308 United Airlines Newark — Chicago	9h 42m including layover	Find flight from$211
15:15 — 20:07	15:15 — 16:53 UA3681 United Airlines Halifax — Newark 1h 32m stop 18:25 — 20:07 UA254 United Airlines Newark — Chicago	6h 52m including layover	Find flight from$381
16:35 — 11:40 +1 day	16:35 — 20:00 PD561 Porter Airlines Halifax — Tampa 13h 53m stop 09:54 — 11:41 F91185 Frontier Airlines Tampa — Chicago	21h 5m including layover	Find flight from$235
16:35 — 09:38 +1 day	16:35 — 20:00 PD561 Porter Airlines Halifax — Tampa 11h 35m stop 07:35 — 09:38 NK1066 Spirit Airlines Tampa — Chicago	19h 3m including layover	Find flight from$263
18:40 — 10:20 +1 day	18:35 — 20:35 PD2284 Porter Airlines Halifax — Toronto 12h 50m stop 09:30 — 10:20 PD2387 Porter Airlines Toronto — Chicago	17h 40m including layover	Find flight from$308
18:40 — 16:40 +1 day	18:35 — 20:35 PD2284 Porter Airlines Halifax — Toronto 19h 10m stop 15:50 — 16:40 PD2393 Porter Airlines Toronto — Chicago	24h including layover	Find flight from$332
20:55 — 10:20 +1 day	19:55 — 21:29 PD210 Porter Airlines Halifax — Toronto 11h 1m stop 09:30 — 10:20 PD2387 Porter Airlines Toronto — Chicago	15h 25m including layover	Find flight from$308
20:55 — 16:40 +1 day	19:55 — 21:29 PD210 Porter Airlines Halifax — Toronto 17h 21m stop 15:50 — 16:40 PD2393 Porter Airlines Toronto — Chicago	21h 45m including layover	Find flight from$332
21:50 — 10:54 +1 day	21:50 — 22:37 AC1599 Air Canada Halifax — Montreal 10h 38m stop 09:15 — 10:54 AC8959 Air Canada Montreal — Chicago	15h 4m including layover	Find flight from$418

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

*Departure and arrival times - local. Updated on May 9, 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 05:00 to 21:50 from 3 Halifax airports and arrive 05:00 to 21:50 to 7 Chicago airports. Average flight time is 16h 20m.

The fastest flight 5h 20m
Average flight time 16h 20m
The earliest flight 05:00
The latest flight 21:50
Distance 1225 ml

The cheapest months to travel to Chicago are january (from 166 $), december (from 196 $), february (from 239 $).

The most expensive months are november (from 307 $), february (from 239 $), december (from 196 $).

What is the lowest airfare Halifax to Chicago?

The cheapest plane ticket found by our users is $166. This airfare is for economy class on one-way PD2280 flight by Porter Airlines for January 12, 2025 which leaves Halifax Int. in Halifax at 08:30 am and arrives at Chicago Midway at 12:00.

Economy class

$166

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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 - 62 departures per week at the price of from $ 342 . And the most expensive tickets are offered by Air Canada airline - from $ 1116.

Direct flights

There’re no direct flights on this route. Try flights with stops.

Connecting Flights

There are 331 flights with layovers on the route. The fastest connecting flight is AC1597 by Air Canada takes 5h 20m and the cheapest is PD2280 by Porter Airlines for $166.

F8 - Freedom Airlines

from $335

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AC - Air Canada

from $342

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PD - Porter Airlines

from $166

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UA - United Airlines

from $208

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WS - WestJet

from $247

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TS - Air Transat

from $303

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See more connecting flights

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 $166
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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?

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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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