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Cheap flights from Halifax to Chicago from C$ 242

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 3/5. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Halifax to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 527Porter Airlines
Mon, 4 May - Mon, 11 May
Porter Airlines Logo
7:00 a.m. - 3:20 p.m.
YHZ
-
MDW
10h 20m
2 stops
Porter Airlines Logo
11:00 a.m. - 7:51 p.m.
MDW
-
YHZ
6h 51m
2 stops
C$ 531Porter Airlines
Fri, 24 Apr - Thu, 30 Apr
Porter Airlines Logo
8:25 a.m. - 12:10 p.m.
YHZ
-
MDW
5h 45m
1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m
1 stop
C$ 538Porter Airlines
Sat, 18 Apr - Wed, 22 Apr
Porter Airlines Logo
8:25 a.m. - 12:10 p.m.
YHZ
-
MDW
5h 45m
1 stop
Porter Airlines Logo
11:00 a.m. - 11:54 p.m.
MDW
-
YHZ
10h 54m
2 stops
C$ 539Porter Airlines
Sat, 18 Apr - Wed, 22 Apr
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
10:25 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 19m
2 stops
C$ 548Porter Airlines
Wed, 29 Jul - Mon, 3 Aug
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 556Porter Airlines
Wed, 29 Jul - Mon, 3 Aug
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 559Porter Airlines
Mon, 4 May - Mon, 11 May
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 571Porter Airlines
Fri, 19 Jun - Mon, 22 Jun
Multiple Airlines Logo
3:45 p.m. - 10:15 a.m.
YHZ
-
MDW
20h 30m
1 stop
Multiple Airlines Logo
10:25 a.m. - 9:25 p.m.
MDW
-
YHZ
9h 00m
1 stop
C$ 572Multiple Airlines
Mon, 27 Apr - Wed, 6 May
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 574Porter Airlines
Wed, 5 Aug - Mon, 10 Aug

Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
4 May
YHZ8:00 a.m.Halifax Intl
8h 35m
2 stops
MDW2:35 p.m.Chicago Midway
11 May
MDW3:20 p.m.Chicago Midway
6h 24m
2 stops
YHZ11:44 p.m.Halifax Intl
C$ 527
Porter Airlines
24 Apr
YHZ7:00 a.m.Halifax Intl
10h 20m
2 stops
MDW3:20 p.m.Chicago Midway
30 Apr
MDW11:00 a.m.Chicago Midway
6h 51m
2 stops
YHZ7:51 p.m.Halifax Intl
C$ 531
Porter Airlines
18 Apr
YHZ8:25 a.m.Halifax Intl
5h 45m
1 stop
MDW12:10 p.m.Chicago Midway
22 Apr
MDW11:00 a.m.Chicago Midway
7h 05m
1 stop
YHZ8:05 p.m.Halifax Intl
C$ 538

WestJet flights from Halifax to Chicago Midway Airport

Our best WestJet deals on Halifax to Chicago Midway Airport flight tickets
WestJet
18 Jun
YHZ1:30 p.m.Halifax Intl
21h 12m
2 stops
MDW8:42 a.m.Chicago Midway
25 Jun
MDW1:00 p.m.Chicago Midway
23h 10m
2 stops
YHZ2:10 p.m.Halifax Intl
C$ 779
WestJet
27 Mar
YHZ8:20 a.m.Halifax Intl
36h 20m
2 stops
MDW6:40 p.m.Chicago Midway
3 Apr
MDW9:35 a.m.Chicago Midway
9h 26m
2 stops
YHZ9:01 p.m.Halifax Intl
C$ 1,051

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 96,600 searches. Data last updated 20 March 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

Mon 4/5

8:00 a.m.-2:35 p.m.

2 stops8h 35m

Chicago Midway

Mon 11/5

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 527

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 24/4

7:00 a.m.-3:20 p.m.

2 stops10h 20m

Chicago Midway

Thu 30/4

11:00 a.m.-7:51 p.m.

2 stops6h 51m

C$ 531
Quickest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 18/4

8:25 a.m.-12:10 p.m.

1 stop5h 45m

Chicago Midway

Wed 22/4

11:00 a.m.-8:05 p.m.

1 stop7h 05m

C$ 538

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 18/4

8:25 a.m.-12:10 p.m.

1 stop5h 45m

Chicago Midway

Wed 22/4

11:00 a.m.-11:54 p.m.

2 stops10h 54m

C$ 539

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 29/7

7:00 a.m.-2:35 p.m.

2 stops9h 35m

Chicago Midway

Mon 3/8

10:25 a.m.-11:44 p.m.

2 stops11h 19m

C$ 548

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 29/7

8:00 a.m.-2:35 p.m.

2 stops8h 35m

Chicago Midway

Mon 3/8

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 556

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 4/5

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Mon 11/5

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 559

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 19/6

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Mon 22/6

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 571

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 27/4

3:45 p.m.-10:15 a.m.

1 stop20h 30m

Chicago Midway

Wed 6/5

10:25 a.m.-9:25 p.m.

1 stop9h 00m

C$ 572

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 5/8

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Mon 10/8

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 574

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 31% 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 01m

Direct flights

None
The fastest flight from Halifax to Chicago Midway Airport takes 5h 01m
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?

    A flight from Halifax Intl to Chicago Midway will travel around 1975.6 km. By plane, this route typically takes 5h 01m.

  • 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?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Munster
Hammond

Why use momondo?

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

Finding the right flight to Chicago from Halifax is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Halifax with this policy.

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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