Cheap flights from Halifax to Chicago from $235

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 9/15. 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

 Logo
6:30 pm - 8:39 amYHZ-MDW
16h 09m1 stop
 Logo
5:20 pm - 8:44 pmMDW-YHZ
25h 24m1 stop
Sat, Sep 6 - Fri, Sep 12
Delta Logo
6:40 am - 5:35 pmYHZ-MDW
12h 55m2 stops
Delta Logo
9:35 am - 11:13 pmMDW-YHZ
11h 38m2 stops
$369Delta
Find Deal
Tue, Sep 16 - Tue, Sep 23
 Logo
11:00 pm - 9:45 amYHZ-MDW
12h 45m1 stop
 Logo
9:35 am - 10:15 pmMDW-YHZ
10h 40m1 stop
Sat, Aug 30 - Sat, Sep 6
Delta Logo
6:40 am - 3:28 pmYHZ-MDW
10h 48m2 stops
Delta Logo
9:31 am - 10:43 pmMDW-YHZ
11h 12m2 stops
$438Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
6:40 am - 3:28 pmYHZ-MDW
10h 48m2 stops
Delta Logo
10:31 am - 11:28 pmMDW-YHZ
10h 57m2 stops
$439Delta
Find Deal
Sat, Aug 23 - Tue, Aug 26
Porter Airlines Logo
9:15 am - 4:24 pmYHZ-MDW
9h 09m2 stops
Porter Airlines Logo
9:40 am - 11:29 pmMDW-YHZ
11h 49m2 stops
$461Porter Airlines
Find Deal
Thu, Aug 21 - Thu, Aug 28
Delta Logo
6:40 am - 3:28 pmYHZ-MDW
10h 48m2 stops
Delta Logo
9:31 am - 10:43 pmMDW-YHZ
11h 12m2 stops
$469Delta
Find Deal
Sat, Aug 30 - Sat, Sep 6
Porter Airlines Logo
5:10 pm - 8:39 amYHZ-MDW
17h 29m1 stop
Porter Airlines Logo
5:20 pm - 1:52 pmMDW-YHZ
18h 32m2 stops
$472Porter Airlines
Find Deal
Sat, Sep 6 - Fri, Sep 12
WestJet Logo
6:30 pm - 5:35 pmYHZ-MDW
25h 05m3 stops
WestJet Logo
7:15 pm - 10:39 pmMDW-YHZ
25h 24m2 stops
$511WestJet
Find Deal
Tue, Sep 16 - Tue, Sep 23
WestJet Logo
8:05 pm - 10:14 pmYHZ-MDW
28h 09m2 stops
WestJet Logo
9:20 am - 7:13 amMDW-YHZ
19h 53m2 stops
$548WestJet
Find Deal
Fri, Oct 10 - Mon, Oct 13

Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
Aug 21
YHZ9:15 amHalifax Intl
9h 09m
2 stops
MDW4:24 pmChicago Midway
Aug 28
MDW9:40 amChicago Midway
11h 49m
2 stops
YHZ11:29 pmHalifax Intl
Porter Airlines
Sep 6
YHZ5:10 pmHalifax Intl
17h 29m
1 stop
MDW8:39 amChicago Midway
Sep 12
MDW5:20 pmChicago Midway
18h 32m
2 stops
YHZ1:52 pmHalifax Intl
Porter Airlines
Sep 14
YHZ6:00 amHalifax Intl
12h 24m
2 stops
MDW4:24 pmChicago Midway
Sep 21
MDW9:35 amChicago Midway
12h 05m
2 stops
YHZ11:40 pmHalifax Intl

Delta flights from Halifax to Chicago Midway Airport

Our best Delta deals on Halifax to Chicago Midway Airport flight tickets
Delta
Sep 16
YHZ6:40 amHalifax Intl
12h 55m
2 stops
MDW5:35 pmChicago Midway
Sep 23
MDW9:35 amChicago Midway
11h 38m
2 stops
YHZ11:13 pmHalifax Intl
Delta
Aug 30
YHZ6:40 amHalifax Intl
10h 48m
2 stops
MDW3:28 pmChicago Midway
Sep 6
MDW9:31 amChicago Midway
11h 12m
2 stops
YHZ10:43 pmHalifax Intl
Delta
Aug 23
YHZ6:40 amHalifax Intl
10h 48m
2 stops
MDW3:28 pmChicago Midway
Aug 26
MDW10:31 amChicago Midway
10h 57m
2 stops
YHZ11:28 pmHalifax Intl

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 August 2, 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

Sat 9/6

6:30 pm-8:39 am

1 stop16h 09m

Chicago Midway

Fri 9/12

5:20 pm-8:44 pm

1 stop25h 24m

$356

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 9/16

6:40 am-5:35 pm

2 stops12h 55m

Chicago Midway

Tue 9/23

9:35 am-11:13 pm

2 stops11h 38m

$369

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 8/30

11:00 pm-9:45 am

1 stop12h 45m

Chicago Midway

Sat 9/6

9:35 am-10:15 pm

1 stop10h 40m

$422

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 8/30

6:40 am-3:28 pm

2 stops10h 48m

Chicago Midway

Sat 9/6

9:31 am-10:43 pm

2 stops11h 12m

$438

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 8/23

6:40 am-3:28 pm

2 stops10h 48m

Chicago Midway

Tue 8/26

10:31 am-11:28 pm

2 stops10h 57m

$439

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 8/21

9:15 am-4:24 pm

2 stops9h 09m

Chicago Midway

Thu 8/28

9:40 am-11:29 pm

2 stops11h 49m

$461

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 8/30

6:40 am-3:28 pm

2 stops10h 48m

Chicago Midway

Sat 9/6

9:31 am-10:43 pm

2 stops11h 12m

$469

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 9/6

5:10 pm-8:39 am

1 stop17h 29m

Chicago Midway

Fri 9/12

5:20 pm-1:52 pm

2 stops18h 32m

$472

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 9/16

6:30 pm-5:35 pm

3 stops25h 05m

Chicago Midway

Tue 9/23

7:15 pm-10:39 pm

2 stops25h 24m

$511

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 10/10

8:05 pm-10:14 pm

2 stops28h 09m

Chicago Midway

Mon 10/13

9:20 am-7:13 am

2 stops19h 53m

$548

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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

Best Price Found

$235

Fastest flight time

6h 49m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Halifax in the past 72 hours is $235. The best round-trip flight deal from Halifax to Chicago Midway Airport found on momondo in the last 72 hours is $356.
The fastest flight from Halifax to Chicago Midway Airport takes 6h 49m
There are no direct flights from Halifax to Chicago Midway Airport. Popular non-direct route for this connection is Halifax Intl Airport - 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 6h 49m.

  • 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
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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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1 adult
Thu 8/7
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