Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Halifax to Chicago from $195

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 4/18. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Halifax to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
7:00 am - 4:50 pm
YHZ
-
MDW
11h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$266Porter Airlines
Fri, Jul 10 - Sun, Jul 19
Porter Airlines Logo
7:00 am - 4:50 pm
YHZ
-
MDW
11h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$279Porter Airlines
Tue, Jul 14 - Sun, Jul 19
Porter Airlines Logo
8:00 am - 4:50 pm
YHZ
-
MDW
10h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$281Porter Airlines
Thu, Jul 9 - Thu, Jul 16
Porter Airlines Logo
7:00 am - 4:50 pm
YHZ
-
MDW
11h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$290Porter Airlines
Fri, Jul 10 - Sat, Jul 18
Porter Airlines Logo
8:00 am - 4:50 pm
YHZ
-
MDW
10h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$305Porter Airlines
Thu, Jul 9 - Mon, Jul 20
Porter Airlines Logo
7:00 am - 4:50 pm
YHZ
-
MDW
11h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$310Porter Airlines
Wed, Jul 8 - Thu, Jul 16
Porter Airlines Logo
8:00 am - 4:50 pm
YHZ
-
MDW
10h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$311Porter Airlines
Tue, Jul 14 - Wed, Jul 15
Porter Airlines Logo
7:00 am - 3:20 pm
YHZ
-
MDW
10h 20m
2 stops
Porter Airlines Logo
11:00 am - 8:05 pm
MDW
-
YHZ
7h 05m
1 stop
$315Porter Airlines
Mon, Apr 20 - Tue, Apr 21
Porter Airlines Logo
7:00 am - 3:20 pm
YHZ
-
MDW
10h 20m
2 stops
Porter Airlines Logo
11:00 am - 11:54 pm
MDW
-
YHZ
10h 54m
2 stops
$320Porter Airlines
Mon, Apr 20 - Tue, Apr 21
Porter Airlines Logo
7:00 am - 4:50 pm
YHZ
-
MDW
11h 50m
2 stops
Porter Airlines Logo
10:25 am - 11:34 pm
MDW
-
YHZ
11h 09m
2 stops
$334Porter Airlines
Wed, Jul 8 - Sat, Jul 18

Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
Jul 10
YHZ7:00 amHalifax Intl
11h 50m
2 stops
MDW4:50 pmChicago Midway
Jul 19
MDW10:25 amChicago Midway
11h 09m
2 stops
YHZ11:34 pmHalifax Intl
$266
Porter Airlines
Jul 14
YHZ7:00 amHalifax Intl
11h 50m
2 stops
MDW4:50 pmChicago Midway
Jul 19
MDW10:25 amChicago Midway
11h 09m
2 stops
YHZ11:34 pmHalifax Intl
$279
Porter Airlines
Jul 9
YHZ8:00 amHalifax Intl
10h 50m
2 stops
MDW4:50 pmChicago Midway
Jul 19
MDW10:25 amChicago Midway
11h 09m
2 stops
YHZ11:34 pmHalifax Intl
$281

WestJet flights from Halifax to Chicago Midway Airport

Our best WestJet deals on Halifax to Chicago Midway Airport flight tickets
WestJet
Jun 19
YHZ1:30 pmHalifax Intl
22h 21m
2 stops
MDW9:51 amChicago Midway
Jun 22
MDW5:59 pmChicago Midway
18h 11m
2 stops
YHZ2:10 pmHalifax Intl
$476
WestJet
Mar 26
YHZ6:00 amHalifax Intl
8h 29m
2 stops
MDW12:29 pmChicago Midway
Apr 2
MDW1:10 pmChicago Midway
34h 31m
2 stops
YHZ1:41 amHalifax Intl
$502
WestJet
Jun 18
YHZ1:30 pmHalifax Intl
21h 12m
2 stops
MDW8:42 amChicago Midway
Jun 25
MDW9:30 amChicago Midway
26h 40m
2 stops
YHZ2:10 pmHalifax Intl
$510

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 February 3, 2026.
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

Fri 7/10

7:00 am-4:50 pm

2 stops11h 50m

Chicago Midway

Sun 7/19

10:25 am-11:34 pm

2 stops11h 09m

$266

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 7/14

7:00 am-4:50 pm

2 stops11h 50m

Chicago Midway

Sun 7/19

10:25 am-11:34 pm

2 stops11h 09m

$279

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 7/9

8:00 am-4:50 pm

2 stops10h 50m

Chicago Midway

Thu 7/16

10:25 am-11:34 pm

2 stops11h 09m

$281

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 7/10

7:00 am-4:50 pm

2 stops11h 50m

Chicago Midway

Sat 7/18

10:25 am-11:34 pm

2 stops11h 09m

$290

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 7/9

8:00 am-4:50 pm

2 stops10h 50m

Chicago Midway

Mon 7/20

10:25 am-11:34 pm

2 stops11h 09m

$305

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 7/8

7:00 am-4:50 pm

2 stops11h 50m

Chicago Midway

Thu 7/16

10:25 am-11:34 pm

2 stops11h 09m

$310

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 7/14

8:00 am-4:50 pm

2 stops10h 50m

Chicago Midway

Wed 7/15

10:25 am-11:34 pm

2 stops11h 09m

$311

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 4/20

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Tue 4/21

11:00 am-8:05 pm

1 stop7h 05m

$315

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 4/20

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Tue 4/21

11:00 am-11:54 pm

2 stops10h 54m

$320

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 7/8

7:00 am-4:50 pm

2 stops11h 50m

Chicago Midway

Sat 7/18

10:25 am-11:34 pm

2 stops11h 09m

$334

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 30% 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

8h 55m

Direct flights

None
The fastest flight from Halifax to Chicago Midway Airport takes 8h 55m
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 8h 55m.

  • 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
Schererville
Valparaiso
Munster
Crown Point
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 3/5
Thu 3/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago