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Cheap flights from Halifax to Chicago from $215

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Halifax to Chicago departing on 1/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
7:00 am - 3:20 pm
YHZ
-
MDW
10h 20m2 stops
Porter Airlines Logo
11:00 am - 8:05 pm
MDW
-
YHZ
7h 05m1 stop
$238Porter Airlines
Tue, Apr 14 - Wed, Apr 15
Porter Airlines Logo
7:00 am - 3:20 pm
YHZ
-
MDW
10h 20m2 stops
Porter Airlines Logo
11:00 am - 8:05 pm
MDW
-
YHZ
7h 05m1 stop
$246Porter Airlines
Tue, Apr 14 - Wed, Apr 15
Porter Airlines Logo
8:30 am - 3:20 pm
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 am - 8:05 pm
MDW
-
YHZ
7h 05m1 stop
$274Porter Airlines
Tue, Apr 14 - Wed, Apr 15
Porter Airlines Logo
8:30 am - 3:20 pm
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 am - 8:05 pm
MDW
-
YHZ
7h 05m1 stop
$282Porter Airlines
Tue, Apr 14 - Wed, Apr 15
Porter Airlines Logo
7:00 am - 3:20 pm
YHZ
-
MDW
10h 20m2 stops
Porter Airlines Logo
11:00 am - 11:54 pm
MDW
-
YHZ
10h 54m2 stops
$295Porter Airlines
Tue, Apr 14 - Wed, Apr 15
Porter Airlines Logo
8:25 am - 3:20 pm
YHZ
-
MDW
8h 55m2 stops
Porter Airlines Logo
11:00 am - 8:05 pm
MDW
-
YHZ
7h 05m1 stop
$299Porter Airlines
Tue, Apr 14 - Wed, Apr 15
Porter Airlines Logo
8:30 am - 3:20 pm
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 am - 9:05 pm
MDW
-
YHZ
8h 05m2 stops
$324Porter Airlines
Thu, Apr 2 - Sun, Apr 5
Porter Airlines Logo
8:30 am - 3:20 pm
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 am - 8:05 pm
MDW
-
YHZ
7h 05m1 stop
$327Porter Airlines
Thu, Apr 2 - Sun, Apr 5
Porter Airlines Logo
8:25 am - 3:20 pm
YHZ
-
MDW
8h 55m2 stops
Porter Airlines Logo
11:00 am - 11:54 pm
MDW
-
YHZ
10h 54m2 stops
$335Porter Airlines
Tue, Apr 14 - Wed, Apr 15
Porter Airlines Logo
7:00 am - 3:20 pm
YHZ
-
MDW
10h 20m2 stops
Porter Airlines Logo
11:00 am - 11:54 pm
MDW
-
YHZ
10h 54m2 stops
$349Porter Airlines
Tue, Apr 14 - Wed, Apr 15

WestJet flights from Halifax to Chicago Midway Airport

Our best WestJet deals on Halifax to Chicago Midway Airport flight tickets
WestJet
Jan 13
YHZ6:00 amHalifax Intl
28h 52m
2 stops
MDW8:52 amChicago Midway
Jan 20
MDW9:32 amChicago Midway
14h 09m
2 stops
YHZ1:41 amHalifax Intl
$409
Find similar
WestJet
Dec 27
YHZ6:00 amHalifax Intl
28h 49m
2 stops
MDW8:49 amChicago Midway
Jan 2
MDW6:08 pmChicago Midway
29h 33m
2 stops
YHZ1:41 amHalifax Intl
$635
Find similar
WestJet
Dec 27
YHZ6:00 amHalifax Intl
28h 49m
2 stops
MDW8:49 amChicago Midway
Jan 2
MDW6:08 pmChicago Midway
29h 33m
2 stops
YHZ1:41 amHalifax Intl
$655
Find similar

Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
Apr 14
YHZ7:00 amHalifax Intl
10h 20m
2 stops
MDW3:20 pmChicago Midway
Apr 15
MDW11:00 amChicago Midway
7h 05m
1 stop
YHZ8:05 pmHalifax Intl
$245
Find similar
Porter Airlines
Apr 14
YHZ7:00 amHalifax Intl
10h 20m
2 stops
MDW3:20 pmChicago Midway
Apr 15
MDW11:00 amChicago Midway
7h 05m
1 stop
YHZ8:05 pmHalifax Intl
$246
Find similar
Porter Airlines
Apr 14
YHZ8:30 amHalifax Intl
8h 50m
1 stop
MDW3:20 pmChicago Midway
Apr 15
MDW11:00 amChicago Midway
7h 05m
1 stop
YHZ8:05 pmHalifax Intl
$274
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Halifax to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Halifax to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$238

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$246

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$274

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$282

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-11:54 pm

2 stops10h 54m

$295

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

8:25 am-3:20 pm

2 stops8h 55m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$299

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 4/2

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Sun 4/5

11:00 am-9:05 pm

2 stops8h 05m

$324

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 4/2

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Sun 4/5

11:00 am-8:05 pm

1 stop7h 05m

$327

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

8:25 am-3:20 pm

2 stops8h 55m

Chicago Midway

Wed 4/15

11:00 am-11:54 pm

2 stops10h 54m

$335

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-11:54 pm

2 stops10h 54m

$349

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Halifax to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Halifax to Chicago Midway Airport flights?

You could potentially save up to 6% on your flight if you consider stops on a Halifax to Chicago Midway Airport flight.

When to book flights from Halifax to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Halifax to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Halifax to Chicago Midway Airport (YHZ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Halifax to Chicago Midway Airport

Fastest flight time

6h 50m

Direct flights

None
The fastest flight from Halifax to Chicago Midway Airport takes 6h 50m
There are no direct flights from Halifax to Chicago Midway Airport. There are no popular flight routes from Halifax to Chicago Midway Airport.
Search flight deals

  • How far is Halifax Intl to Chicago Midway by plane?

    Chicago Midway is 1227.6 mi away from Halifax Intl. By plane, this route typically takes 6h 50m.

  • When did momondo last update prices for flights from Halifax Intl Airport to Chicago Midway Airport?

    Prices for flights from Halifax Intl Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Halifax Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Halifax Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Halifax to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Halifax.

Can I find flights from Halifax to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Halifax which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Halifax to Chicago?

momondo helps you find the best flight between Halifax and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Halifax to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Halifax to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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