How do I get Price Alerts for flights from Vancouver to Chicago Midway Airport?

Confirm your travel details to search for the latest offers for flights from Vancouver to Chicago Midway Airport . While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

How can I save money on flights from Vancouver to Chicago Midway Airport with momondo?

By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

How does momondo find its flight prices?

We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

How old do you have to be to fly from Vancouver 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 Vancouver to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 160 Cheap Flights from Vancouver to Chicago Midway Airport in 2025/26

1 adult

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Find the cheapest flights from Vancouver to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:30 p.m. - 11:55 a.m.

YVR

MDW

11h 25m1 stop

3:29 p.m. - 11:59 p.m.

MDW

YVR

10h 30m1 stop

C$ 391Multiple Airlines

Fri, 20 Feb - Mon, 23 Feb

12:05 p.m. - 11:51 p.m.

YVR

MDW

9h 46m1 stop

11:05 a.m. - 9:25 p.m.

MDW

YVR

12h 20m2 stops

C$ 394Multiple Airlines

Thu, 19 Feb - Tue, 24 Feb

11:00 p.m. - 11:27 a.m.

YVR

MDW

10h 27m1 stop

3:26 p.m. - 11:59 p.m.

MDW

YVR

10h 33m1 stop

C$ 402Multiple Airlines

Wed, 18 Feb - Fri, 27 Feb

12:05 p.m. - 11:51 p.m.

YVR

MDW

9h 46m1 stop

11:05 a.m. - 9:08 p.m.

MDW

YVR

12h 03m1 stop

C$ 404Multiple Airlines

Thu, 19 Feb - Thu, 26 Feb

7:30 a.m. - 11:09 p.m.

YVR

MDW

13h 39m1 stop

11:39 a.m. - 10:45 p.m.

MDW

YVR

13h 06m2 stops

C$ 424Multiple Airlines

Mon, 12 Jan - Wed, 14 Jan

11:00 p.m. - 11:27 a.m.

YVR

MDW

10h 27m1 stop

12:50 p.m. - 9:25 p.m.

MDW

YVR

10h 35m2 stops

C$ 437Multiple Airlines

Wed, 18 Feb - Sat, 21 Feb

7:45 p.m. - 10:31 a.m.

YVR

MDW

12h 46m2 stops

11:05 a.m. - 9:15 p.m.

MDW

YVR

12h 10m1 stop

C$ 457Multiple Airlines

Tue, 13 Jan - Tue, 20 Jan

5:00 p.m. - 8:52 a.m.

YVR

MDW

13h 52m2 stops

7:30 a.m. - 11:59 p.m.

MDW

YVR

18h 29m1 stop

C$ 464Multiple Airlines

Fri, 30 Jan - Fri, 6 Feb

5:00 p.m. - 8:52 a.m.

YVR

MDW

13h 52m2 stops

7:30 a.m. - 11:59 p.m.

MDW

YVR

18h 29m1 stop

C$ 467Multiple Airlines

Fri, 30 Jan - Fri, 6 Feb

7:37 p.m. - 8:52 a.m.

YVR

MDW

11h 15m2 stops

9:50 a.m. - 8:54 p.m.

MDW

YVR

13h 04m2 stops

C$ 488Delta

Tue, 20 Jan - Tue, 27 Jan

Porter Airlines flights from Vancouver to Chicago Midway Airport

Our best Porter Airlines deals on Vancouver to Chicago Midway Airport flight tickets

Porter Airlines

15 Jan

YVR12:20 p.m.Vancouver Intl

19h 50m

2 stops

MDW10:10 a.m.Chicago Midway

22 Jan

MDW11:05 a.m.Chicago Midway

12h 20m

2 stops

YVR9:25 p.m.Vancouver Intl

C$ 539

Find similar

Porter Airlines

15 Jan

YVR12:20 p.m.Vancouver Intl

19h 45m

2 stops

MDW10:05 a.m.Chicago Midway

18 Jan

MDW11:00 a.m.Chicago Midway

11h 43m

2 stops

YVR8:43 p.m.Vancouver Intl

C$ 557

Find similar

Porter Airlines

19 Jan

YVR12:20 p.m.Vancouver Intl

19h 45m

2 stops

MDW10:05 a.m.Chicago Midway

31 Jan

MDW12:45 p.m.Chicago Midway

10h 40m

2 stops

YVR9:25 p.m.Vancouver Intl

C$ 712

Find similar

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets

WestJet

13 Jan

YVR10:30 p.m.Vancouver Intl

17h 04m

2 stops

MDW5:34 p.m.Chicago Midway

15 Jan

MDW1:28 p.m.Chicago Midway

13h 16m

2 stops

YVR12:44 a.m.Vancouver Intl

C$ 606

Find similar

WestJet

23 Jan

YVR10:30 p.m.Vancouver Intl

12h 16m

2 stops

MDW12:46 p.m.Chicago Midway

26 Jan

MDW10:46 a.m.Chicago Midway

12h 29m

2 stops

YVR9:15 p.m.Vancouver Intl

C$ 623

Find similar

WestJet

27 Mar

YVR6:00 a.m.Vancouver Intl

24h 46m

2 stops

MDW8:46 a.m.Chicago Midway

31 Mar

MDW7:20 p.m.Chicago Midway

27h 48m

2 stops

YVR9:08 p.m.Vancouver Intl

C$ 634

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Vancouver to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 20/2

10:30 p.m.-11:55 a.m.

1 stop11h 25m

Chicago Midway

Mon 23/2

3:29 p.m.-11:59 p.m.

1 stop10h 30m

C$ 391

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 19/2

12:05 p.m.-11:51 p.m.

1 stop9h 46m

Chicago Midway

Tue 24/2

11:05 a.m.-9:25 p.m.

2 stops12h 20m

C$ 394

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 18/2

11:00 p.m.-11:27 a.m.

1 stop10h 27m

Chicago Midway

Fri 27/2

3:26 p.m.-11:59 p.m.

1 stop10h 33m

C$ 402

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 19/2

12:05 p.m.-11:51 p.m.

1 stop9h 46m

Chicago Midway

Thu 26/2

11:05 a.m.-9:08 p.m.

1 stop12h 03m

C$ 404

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 12/1

7:30 a.m.-11:09 p.m.

1 stop13h 39m

Chicago Midway

Wed 14/1

11:39 a.m.-10:45 p.m.

2 stops13h 06m

C$ 424

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 18/2

11:00 p.m.-11:27 a.m.

1 stop10h 27m

Chicago Midway

Sat 21/2

12:50 p.m.-9:25 p.m.

2 stops10h 35m

C$ 437

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 13/1

7:45 p.m.-10:31 a.m.

2 stops12h 46m

Chicago Midway

Tue 20/1

11:05 a.m.-9:15 p.m.

1 stop12h 10m

C$ 457

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 30/1

5:00 p.m.-8:52 a.m.

2 stops13h 52m

Chicago Midway

Fri 6/2

7:30 a.m.-11:59 p.m.

1 stop18h 29m

C$ 464

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 30/1

5:00 p.m.-8:52 a.m.

2 stops13h 52m

Chicago Midway

Fri 6/2

7:30 a.m.-11:59 p.m.

1 stop18h 29m

C$ 467

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 20/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Tue 27/1

9:50 a.m.-8:54 p.m.

2 stops13h 04m

C$ 488

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

Cheap Vancouver to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vancouver to Chicago Midway Airport

Fastest flight time	8h 51m
Direct flights	None

The fastest flight from Vancouver to Chicago Midway Airport takes 8h 51m

There are no direct flights from Vancouver to Chicago Midway Airport. There are no popular flight routes from Vancouver to Chicago Midway Airport.

Search flight deals

How far is Vancouver to Chicago Midway by plane?
Vancouver and Chicago Midway are 2846.7 km apart from one another. Flights usually cover this in 8h 51m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Vancouver to Chicago Midway Airport?
Prices for flights from Vancouver to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Vancouver 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 Vancouver to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

How do I get Price Alerts for flights from Vancouver to Chicago Midway Airport?
Confirm your travel details to search for the latest offers for flights from Vancouver to Chicago Midway Airport. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.
How can I save money on flights from Vancouver to Chicago Midway Airport with momondo?
By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.
How does momondo find its flight prices?
We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Munster

Hammond

Merrillville

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Vancouver to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. All flights to Chicago from Vancouver on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Vancouver to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Vancouver. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Vancouver to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Vancouver 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.