What is the cheapest month to book a flight from Vancouver Intl Airport to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago Midway Airport (average of $160). Flying from Vancouver Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

How far in advance should I book a flight from Vancouver Intl Airport to Chicago Midway Airport?

Find a great deal and save up to 21% by booking at least 33 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Vancouver Intl Airport to Chicago Midway Airport within the next two weeks, with the cheapest ticket starting at $235.

What is the cheapest month to fly from Vancouver Intl Airport to Chicago Midway Airport?

The best pricing can be found in the month of April. Prices to Chicago Midway Airport from Vancouver Intl Airport average $352. You can even find prices in April for less than $352, as users have found deals to Chicago Midway Airport from as low as $165. The month of December appears to be one of the more expensive times to travel to Chicago Midway Airport from Vancouver Intl Airport. Flying in the targeted month can save you up to 21%.

What is the cheapest time of day to fly from YVR to MDW?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Vancouver Intl Airport to Chicago Midway Airport as you normally would.

Can I find deals for flights from Vancouver Intl to Midway that include hotel bookings?

Yes. In addition to deals on Vancouver Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Vancouver Intl to Midway?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vancouver Intl to Midway.

Can I find deals for business class flights from Vancouver Intl to Midway?

Yes. Cheapflights offers flight deals from Vancouver Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$151+ Cheap Flights from Vancouver Intl Airport to Chicago Midway Airport

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Cheap flight deals from Vancouver Intl to Midway

Round-trip from	$237 (Kiwi.com)
One-way from	$151 (Kiwi.com)
Popular in	December
Cheapest in	April
Average price	$330

From Vancouver Intl to Chicago Midway

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One-way flight from Vancouver Intl to Chicago Midway

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Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).

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Average for round-trip flights in August 2025

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Find flight deals from Vancouver Intl to Midway

Cheapest flights from Vancouver Intl to Midway
Explore the most affordable flight options available from Vancouver Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

Mon 9/2211:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Thu 9/256:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$237

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Wed 9/249:00 amMDW - YVR

1 stop13h 48mMultiple Airlines

Deal found 8/16

$240

Fri 9/59:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/146:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$242

Mon 9/811:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Wed 9/249:00 amMDW - YVR

1 stop13h 48mMultiple Airlines

Deal found 8/16

$245

Tue 9/97:45 pmYVR - MDW

2 stops11h 05mDelta

Tue 9/231:08 pmMDW - YVR

2 stops9h 23mDelta

Deal found 8/16

$246

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/216:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$250

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/286:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$251

Thu 9/188:30 pmYVR - MDW

2 stops24h 50mMultiple Airlines

Mon 9/226:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/15

$253

Mon 9/811:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Sun 9/216:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$255

Fri 9/129:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Mon 9/156:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$257

Thu 9/118:30 pmYVR - MDW

2 stops17h 30mMultiple Airlines

Mon 9/156:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$258

Wed 10/18:30 pmYVR - MDW

2 stops17h 28mMultiple Airlines

Wed 10/88:05 amMDW - YVR

1 stop14h 43mMultiple Airlines

Deal found 8/16

$260

Best flights from Vancouver Intl to Midway
Discover carefully curated flight deals from Vancouver Intl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 18, 2025.

Mon 9/2211:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Thu 9/256:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$237

Wed 9/106:15 amYVR - MDW

1 stop9h 22mDelta

Tue 9/231:08 pmMDW - YVR

2 stops12h 50mDelta

Deal found 8/16

$246

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Wed 9/249:00 amMDW - YVR

1 stop13h 48mMultiple Airlines

Deal found 8/16

$240

Sat 9/135:55 amYVR - MDW

1 stop9h 40mDelta

Tue 9/231:43 pmMDW - YVR

2 stops12h 15mDelta

Deal found 8/16

$246

Tue 10/148:30 pmYVR - MDW

2 stops15h 08mMultiple Airlines

Sat 10/186:15 amMDW - YVR

1 stop16h 33mMultiple Airlines

Deal found 8/16

$240

Fri 9/127:44 pmYVR - MDW

2 stops11h 09mDelta

Tue 9/231:08 pmMDW - YVR

2 stops9h 23mDelta

Deal found 8/16

$246

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sat 9/276:15 amMDW - YVR

1 stop16h 33mMultiple Airlines

Deal found 8/16

$240

Sat 9/135:55 amYVR - MDW

1 stop9h 40mDelta

Wed 9/249:35 amMDW - YVR

2 stops12h 56mDelta

Deal found 8/16

$246

Fri 9/59:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/146:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$242

Tue 9/97:45 pmYVR - MDW

2 stops11h 05mDelta

Tue 9/231:08 pmMDW - YVR

2 stops9h 23mDelta

Deal found 8/16

$246

Mon 9/811:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Wed 9/249:00 amMDW - YVR

1 stop13h 48mMultiple Airlines

Deal found 8/16

$245

Last-minute flights from Vancouver Intl to Midway
Discover last-minute flight deals from Vancouver Intl to Midway. Data last updated August 18, 2025 and is based on user searches.

Fri 9/59:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/146:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$242

Mon 9/811:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Wed 9/249:00 amMDW - YVR

1 stop13h 48mMultiple Airlines

Deal found 8/16

$245

Mon 9/811:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Sun 9/216:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$255

Tue 9/97:45 pmYVR - MDW

2 stops11h 05mDelta

Tue 9/231:08 pmMDW - YVR

2 stops9h 23mDelta

Deal found 8/16

$246

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Wed 9/249:00 amMDW - YVR

1 stop13h 48mMultiple Airlines

Deal found 8/16

$240

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/216:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$250

Thu 9/119:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/286:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$251

Thu 9/118:30 pmYVR - MDW

2 stops17h 30mMultiple Airlines

Mon 9/156:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$258

Fri 9/129:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Mon 9/156:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$257

Fri 9/129:30 amYVR - MDW

1 stop11h 50mMultiple Airlines

Sun 9/286:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$261

Thu 9/188:30 pmYVR - MDW

2 stops24h 50mMultiple Airlines

Mon 9/226:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/15

$253

Mon 9/2211:00 pmYVR - MDW

1 stop14h 58mMultiple Airlines

Thu 9/256:20 amMDW - YVR

1 stop16h 28mMultiple Airlines

Deal found 8/16

$237

One-way flights from Vancouver Intl to Midway
Search for one-way flight options from Vancouver Intl to Midway. Find affordable one-way fares based on user searches. Data last updated August 18, 2025.

Fri 10/109:30 amYVR - MDW

2 stops48h 14mMultiple Airlines

Deal found 8/15

$151

Tue 10/219:30 amYVR - MDW

1 stop26h 08mMultiple Airlines

Deal found 8/18

$152

Sun 10/196:00 amYVR - MDW

2 stops24h 31mMultiple Airlines

Deal found 8/17

$154

Wed 9/37:30 pmYVR - MDW

2 stops18h 28mMultiple Airlines

Deal found 8/18

$156

Wed 9/249:30 amYVR - MDW

2 stops49h 14mMultiple Airlines

Deal found 8/17

$158

Sat 10/48:30 pmYVR - MDW

3 stops38h 14mMultiple Airlines

Deal found 8/16

$164

Sat 9/611:00 pmYVR - MDW

2 stops35h 44mMultiple Airlines

Deal found 8/16

$169

Tue 8/266:15 amYVR - MDW

1 stop9h 22mDelta

Deal found 8/16

$172

Sat 9/139:20 amYVR - MDW

2 stops11h 57mMultiple Airlines

Deal found 8/16

$173

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 9/22

11:00 pm-3:58 pm

1 stop14h 58m

Chicago Midway

Thu 9/25

6:20 am-8:48 pm

1 stop16h 28m

$237

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 9/11

9:30 am-11:20 pm

1 stop11h 50m

Chicago Midway

Wed 9/24

9:00 am-8:48 pm

1 stop13h 48m

$240

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/14

8:30 pm-1:38 pm

2 stops15h 08m

Chicago Midway

Sat 10/18

6:15 am-8:48 pm

1 stop16h 33m

$240

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 9/11

9:30 am-11:20 pm

1 stop11h 50m

Chicago Midway

Sat 9/27

6:15 am-8:48 pm

1 stop16h 33m

$240

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/5

9:30 am-11:20 pm

1 stop11h 50m

Chicago Midway

Sun 9/14

6:20 am-8:48 pm

1 stop16h 28m

$242

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 9/8

11:00 pm-3:58 pm

1 stop14h 58m

Chicago Midway

Wed 9/24

9:00 am-8:48 pm

1 stop13h 48m

$245

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 9/10

6:15 am-5:37 pm

1 stop9h 22m

Chicago Midway

Tue 9/23

1:08 pm-11:58 pm

2 stops12h 50m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 9/13

5:55 am-5:35 pm

1 stop9h 40m

Chicago Midway

Tue 9/23

1:43 pm-11:58 pm

2 stops12h 15m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/12

7:44 pm-8:53 am

2 stops11h 09m

Chicago Midway

Tue 9/23

1:08 pm-8:31 pm

2 stops9h 23m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 9/13

5:55 am-5:35 pm

1 stop9h 40m

Chicago Midway

Wed 9/24

9:35 am-8:31 pm

2 stops12h 56m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 20 results

Best time to book a flight from Vancouver Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Vancouver Intl with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Can I find deals for flights from Vancouver Intl to Midway that include hotel bookings?
Yes. In addition to deals on Vancouver Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Vancouver Intl to Midway?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Vancouver Intl to Midway.
Can I find deals for business class flights from Vancouver Intl to Midway?
Yes. Cheapflights offers flight deals from Vancouver Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Vancouver Intl Airport to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Vancouver Intl Airport to Chicago Midway Airport (average of $160). Flying from Vancouver Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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$151+ Cheap flights from Vancouver Intl (YVR) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/10. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Vancouver Intl to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Vancouver Intl to Midway

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Vancouver Intl to Midway

Cheapest flights from Vancouver Intl to MidwayExplore the most affordable flight options available from Vancouver Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

Explore the most affordable flight options available from Vancouver Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Vancouver Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Vancouver Intl with our price prediction graph.

Related info for your journey

Find useful and relevant information for your journey from Vancouver Intl to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

Can I find deals for flights from Vancouver Intl to Midway that include hotel bookings?

How can I find direct flights from Vancouver Intl to Midway?

Can I find deals for business class flights from Vancouver Intl to Midway?

What is the cheapest month to book a flight from Vancouver Intl Airport to Chicago Midway Airport?

Traveling to a place near Chicago Midway Airport?

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Cheapest flights from Vancouver Intl to Midway
Explore the most affordable flight options available from Vancouver Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 18, 2025.