Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Halifax to Chicago from $110

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 10/1. 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

Porter Airlines Logo
9:15 am - 4:24 pmYHZ-MDW
9h 09m2 stops
Porter Airlines Logo
11:00 am - 11:54 pmMDW-YHZ
10h 54m2 stops
$220Porter Airlines
Find Deal
Wed, Oct 22 - Wed, Oct 29
Porter Airlines Logo
8:30 am - 3:20 pmYHZ-MDW
8h 50m1 stop
Porter Airlines Logo
11:00 am - 8:05 pmMDW-YHZ
7h 05m1 stop
$229Porter Airlines
Find Deal
Sun, Nov 9 - Thu, Nov 20
Porter Airlines Logo
9:15 am - 4:24 pmYHZ-MDW
9h 09m2 stops
Porter Airlines Logo
11:00 am - 8:05 pmMDW-YHZ
7h 05m1 stop
$235Porter Airlines
Find Deal
Wed, Oct 22 - Wed, Oct 29
Porter Airlines Logo
8:25 am - 3:20 pmYHZ-MDW
8h 55m2 stops
Porter Airlines Logo
11:00 am - 8:05 pmMDW-YHZ
7h 05m1 stop
$261Porter Airlines
Find Deal
Fri, Nov 7 - Tue, Nov 11
Porter Airlines Logo
8:30 am - 3:20 pmYHZ-MDW
8h 50m1 stop
Porter Airlines Logo
11:00 am - 8:05 pmMDW-YHZ
7h 05m1 stop
$269Porter Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
Multiple Airlines Logo
8:30 am - 3:20 pmYHZ-MDW
8h 50m1 stop
Multiple Airlines Logo
9:27 am - 12:12 pmMDW-YHZ
24h 45m2 stops
$331Multiple Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
Multiple Airlines Logo
6:30 pm - 8:39 amYHZ-MDW
16h 09m1 stop
Multiple Airlines Logo
9:35 am - 11:40 pmMDW-YHZ
12h 05m2 stops
$344Multiple Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 25
WestJet Logo
8:30 am - 10:14 pmYHZ-MDW
15h 44m2 stops
WestJet Logo
10:35 am - 10:39 pmMDW-YHZ
10h 04m2 stops
$433WestJet
Find Deal
Sat, Oct 11 - Sat, Oct 25
WestJet Logo
8:30 am - 10:14 pmYHZ-MDW
15h 44m2 stops
WestJet Logo
7:10 pm - 8:44 pmMDW-YHZ
23h 34m2 stops
$459WestJet
Find Deal
Sat, Oct 18 - Tue, Oct 21
Delta Logo
8:30 am - 6:25 pmYHZ-MDW
11h 55m2 stops
Delta Logo
9:35 am - 1:42 amMDW-YHZ
14h 07m2 stops
$481Delta
Find Deal
Mon, Oct 13 - Sun, Oct 26

Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
Oct 22
YHZ9:15 amHalifax Intl
9h 09m
2 stops
MDW4:24 pmChicago Midway
Oct 29
MDW11:00 amChicago Midway
10h 54m
2 stops
YHZ11:54 pmHalifax Intl
$220
Find similar
Porter Airlines
Nov 9
YHZ8:30 amHalifax Intl
8h 50m
1 stop
MDW3:20 pmChicago Midway
Nov 20
MDW11:00 amChicago Midway
7h 05m
1 stop
YHZ8:05 pmHalifax Intl
$229
Find similar
Porter Airlines
Oct 22
YHZ9:15 amHalifax Intl
9h 09m
2 stops
MDW4:24 pmChicago Midway
Oct 29
MDW11:00 amChicago Midway
7h 05m
1 stop
YHZ8:05 pmHalifax Intl
$235
Find similar

WestJet flights from Halifax to Chicago Midway Airport

Our best WestJet deals on Halifax to Chicago Midway Airport flight tickets
WestJet
Oct 11
YHZ8:30 amHalifax Intl
15h 44m
2 stops
MDW10:14 pmChicago Midway
Oct 25
MDW10:35 amChicago Midway
10h 04m
2 stops
YHZ10:39 pmHalifax Intl
$433
Find similar
WestJet
Oct 18
YHZ8:30 amHalifax Intl
15h 44m
2 stops
MDW10:14 pmChicago Midway
Oct 21
MDW7:10 pmChicago Midway
23h 34m
2 stops
YHZ8:44 pmHalifax Intl
$459
Find similar
WestJet
Dec 26
YHZ6:00 amHalifax Intl
37h 19m
2 stops
MDW5:19 pmChicago Midway
Jan 1
MDW11:48 amChicago Midway
17h 40m
2 stops
YHZ7:28 amHalifax Intl
$604
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 September 17, 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

Wed 10/22

9:15 am-4:24 pm

2 stops9h 09m

Chicago Midway

Wed 10/29

11:00 am-11:54 pm

2 stops10h 54m

$220

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 11/9

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Thu 11/20

11:00 am-8:05 pm

1 stop7h 05m

$229

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 10/22

9:15 am-4:24 pm

2 stops9h 09m

Chicago Midway

Wed 10/29

11:00 am-8:05 pm

1 stop7h 05m

$235

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 11/7

8:25 am-3:20 pm

2 stops8h 55m

Chicago Midway

Tue 11/11

11:00 am-8:05 pm

1 stop7h 05m

$261

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 11/13

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Mon 11/17

11:00 am-8:05 pm

1 stop7h 05m

$269

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 11/13

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Mon 11/17

9:27 am-12:12 pm

2 stops24h 45m

$331

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 10/11

6:30 pm-8:39 am

1 stop16h 09m

Chicago Midway

Sat 10/25

9:35 am-11:40 pm

2 stops12h 05m

$344

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 10/11

8:30 am-10:14 pm

2 stops15h 44m

Chicago Midway

Sat 10/25

10:35 am-10:39 pm

2 stops10h 04m

$433

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 10/18

8:30 am-10:14 pm

2 stops15h 44m

Chicago Midway

Tue 10/21

7:10 pm-8:44 pm

2 stops23h 34m

$459

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 10/13

8:30 am-6:25 pm

2 stops11h 55m

Chicago Midway

Sun 10/26

9:35 am-1:42 am

2 stops14h 07m

$481

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 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

Direct flights

None
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 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
Lansing
Portage
Schererville
Valparaiso
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.

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
Fri 10/17
Fri 10/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago