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

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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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 Arrival 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 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
    Find
  • AC - Air Canada
    from $342
    Find
  • PD - Porter Airlines
    from $166
    Find
  • UA - United Airlines
    from $208
    Find
  • WS - WestJet
    from $247
    Find
  • TS - Air Transat
    from $303
    Find
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
    Find
  • Halifax Int.-YHZ
    from $166
    Find
  • Shearwater-YAW
    Find

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
    Find
  • Chicago NAS-NOH
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • 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.

    To find a plane ticket, please select dates.

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