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Cheap flights from Halifax to Chicago from $193

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 6/14. 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

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 - 2:35 pm
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
3:20 pm - 11:44 pm
MDW
-
YHZ
6h 24m
2 stops
$393Porter Airlines
Fri, Jun 19 - Mon, Jun 22
Porter Airlines Logo
7:00 am - 2:35 pm
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
10:15 am - 11:44 pm
MDW
-
YHZ
11h 29m
2 stops
$397Porter Airlines
Mon, Jun 1 - Mon, Jun 8
Delta Logo
1:27 pm - 10:17 pm
YHZ
-
MDW
10h 50m
2 stops
Delta Logo
9:54 am - 11:07 pm
MDW
-
YHZ
11h 13m
2 stops
$399Delta
Wed, Jun 10 - Sat, Jun 20
Porter Airlines Logo
8:00 am - 2:35 pm
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 pm - 11:44 pm
MDW
-
YHZ
6h 24m
2 stops
$401Porter Airlines
Sun, Jun 14 - Sun, Jun 21
Porter Airlines Logo
8:00 am - 2:35 pm
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
3:20 pm - 11:44 pm
MDW
-
YHZ
6h 24m
2 stops
$402Porter Airlines
Sun, Jun 14 - Sun, Jun 21
Porter Airlines Logo
7:00 am - 2:35 pm
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
3:20 pm - 11:44 pm
MDW
-
YHZ
6h 24m
2 stops
$417Porter Airlines
Fri, Jun 19 - Mon, Jun 22
Multiple Airlines Logo
11:00 pm - 9:40 am
YHZ
-
MDW
12h 40m
1 stop
Multiple Airlines Logo
10:25 am - 10:45 am
MDW
-
YHZ
22h 20m
1 stop
$418Multiple Airlines
Sat, Jun 20 - Sat, Jun 27
Porter Airlines Logo
8:00 am - 2:35 pm
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:15 am - 9:14 pm
MDW
-
YHZ
8h 59m
2 stops
$421Porter Airlines
Mon, Jun 1 - Mon, Jun 8
Porter Airlines Logo
8:00 am - 2:35 pm
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:15 am - 11:44 pm
MDW
-
YHZ
11h 29m
2 stops
$422Porter Airlines
Mon, Jun 8 - Thu, Jun 11
Porter Airlines Logo
8:00 am - 2:35 pm
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 pm - 11:44 pm
MDW
-
YHZ
6h 24m
2 stops
$423Porter Airlines
Fri, Jun 19 - Mon, Jun 22

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Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
Jun 19
YHZ7:00 amHalifax Intl
9h 35m
2 stops
MDW2:35 pmChicago Midway
Jun 22
MDW3:20 pmChicago Midway
6h 24m
2 stops
YHZ11:44 pmHalifax Intl
$393
Porter Airlines
Jun 1
YHZ7:00 amHalifax Intl
9h 35m
2 stops
MDW2:35 pmChicago Midway
Jun 8
MDW10:15 amChicago Midway
11h 29m
2 stops
YHZ11:44 pmHalifax Intl
$397
Porter Airlines
Jun 14
YHZ8:00 amHalifax Intl
8h 35m
1 stop
MDW2:35 pmChicago Midway
Jun 21
MDW3:20 pmChicago Midway
6h 24m
2 stops
YHZ11:44 pmHalifax Intl
$401

Delta flights from Halifax to Chicago Midway Airport

Our best Delta deals on Halifax to Chicago Midway Airport flight tickets
Delta
Jun 10
YHZ1:27 pmHalifax Intl
10h 50m
2 stops
MDW10:17 pmChicago Midway
Jun 20
MDW9:54 amChicago Midway
11h 13m
2 stops
YHZ11:07 pmHalifax Intl
$399
Delta
Jun 10
YHZ3:30 pmHalifax Intl
5h 01m
1 stop
MDW6:31 pmChicago Midway
Jun 20
MDW1:21 pmChicago Midway
6h 24m
1 stop
YHZ9:45 pmHalifax Intl
$442
Delta
May 29
YHZ3:30 pmHalifax Intl
5h 03m
1 stop
MDW6:33 pmChicago Midway
Jun 3
MDW1:22 pmChicago Midway
6h 18m
1 stop
YHZ9:40 pmHalifax Intl
$443

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 May 4, 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

Cheapest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 6/19

7:00 am-2:35 pm

2 stops9h 35m

Chicago Midway

Mon 6/22

3:20 pm-11:44 pm

2 stops6h 24m

$393

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 6/1

7:00 am-2:35 pm

2 stops9h 35m

Chicago Midway

Mon 6/8

10:15 am-11:44 pm

2 stops11h 29m

$397

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 6/10

1:27 pm-10:17 pm

2 stops10h 50m

Chicago Midway

Sat 6/20

9:54 am-11:07 pm

2 stops11h 13m

$399
Quickest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 6/14

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Sun 6/21

3:20 pm-11:44 pm

2 stops6h 24m

$401

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 6/14

8:00 am-2:35 pm

2 stops8h 35m

Chicago Midway

Sun 6/21

3:20 pm-11:44 pm

2 stops6h 24m

$402

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 6/19

7:00 am-2:35 pm

2 stops9h 35m

Chicago Midway

Mon 6/22

3:20 pm-11:44 pm

2 stops6h 24m

$417

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 6/20

11:00 pm-9:40 am

1 stop12h 40m

Chicago Midway

Sat 6/27

10:25 am-10:45 am

1 stop22h 20m

$418

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 6/1

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Mon 6/8

10:15 am-9:14 pm

2 stops8h 59m

$421

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 6/8

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Thu 6/11

10:15 am-11:44 pm

2 stops11h 29m

$422

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 6/19

8:00 am-2:35 pm

1 stop8h 35m

Chicago Midway

Mon 6/22

3:20 pm-11:44 pm

2 stops6h 24m

$423

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 37% 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

5h 03m

Direct flights

None
The fastest flight from Halifax to Chicago Midway Airport takes 5h 03m
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

Frequently asked questions about flying from Halifax to Chicago Midway Airport

  • 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 5h 03m.

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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