Cheap flights from Vancouver to Chicago from $122

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Vancouver to Chicago departing on 1/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:00 pm - 10:05 amYVR-MDW
15h 05m1 stop
Multiple Airlines Logo
6:00 am - 10:40 pmMDW-YVR
18h 40m2 stops
$307Multiple Airlines
Find Deal
Thu, Mar 5 - Tue, Mar 10
Multiple Airlines Logo
11:00 pm - 11:33 amYVR-MDW
10h 33m1 stop
Multiple Airlines Logo
11:00 am - 10:38 pmMDW-YVR
13h 38m2 stops
$319Multiple Airlines
Find Deal
Sun, Apr 12 - Sun, Apr 19
Multiple Airlines Logo
11:00 pm - 11:33 amYVR-MDW
10h 33m1 stop
Multiple Airlines Logo
4:15 pm - 12:57 pmMDW-YVR
22h 42m1 stop
$322Multiple Airlines
Find Deal
Sun, Apr 12 - Sun, Apr 19
Multiple Airlines Logo
11:00 pm - 11:33 amYVR-MDW
10h 33m1 stop
Multiple Airlines Logo
11:00 am - 10:38 pmMDW-YVR
13h 38m2 stops
$324Multiple Airlines
Find Deal
Sun, Apr 12 - Sun, Apr 19
Multiple Airlines Logo
11:00 pm - 11:33 amYVR-MDW
10h 33m1 stop
Multiple Airlines Logo
4:15 pm - 11:29 amMDW-YVR
21h 14m1 stop
$333Multiple Airlines
Find Deal
Sun, Apr 12 - Wed, Apr 15
Multiple Airlines Logo
5:00 pm - 10:05 amYVR-MDW
15h 05m1 stop
Multiple Airlines Logo
11:00 am - 9:08 pmMDW-YVR
12h 08m1 stop
$335Multiple Airlines
Find Deal
Wed, Apr 15 - Sun, Apr 19
Multiple Airlines Logo
11:00 pm - 8:46 amYVR-MDW
31h 46m1 stop
Multiple Airlines Logo
2:49 pm - 12:10 amMDW-YVR
11h 21m2 stops
$338Multiple Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 10
Multiple Airlines Logo
12:10 am - 3:20 pmYVR-MDW
13h 10m1 stop
Multiple Airlines Logo
4:15 pm - 11:50 amMDW-YVR
21h 35m1 stop
$344Multiple Airlines
Find Deal
Sat, Apr 11 - Wed, Apr 15
Multiple Airlines Logo
12:10 am - 3:20 pmYVR-MDW
13h 10m1 stop
Multiple Airlines Logo
11:00 am - 10:38 pmMDW-YVR
13h 38m2 stops
$346Multiple Airlines
Find Deal
Sat, Apr 11 - Sun, Apr 19
Multiple Airlines Logo
12:10 am - 3:20 pmYVR-MDW
13h 10m1 stop
Multiple Airlines Logo
11:00 am - 9:08 pmMDW-YVR
12h 08m1 stop
$348Multiple Airlines
Find Deal
Sat, Apr 11 - Sun, Apr 19

Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets
Delta
Jan 26
YVR7:37 pmVancouver Intl
12h 16m
2 stops
MDW9:53 amChicago Midway
Jan 31
MDW10:46 amChicago Midway
12h 08m
2 stops
YVR8:54 pmVancouver Intl
Delta
Mar 5
YVR7:37 pmVancouver Intl
11h 16m
2 stops
MDW8:53 amChicago Midway
Mar 10
MDW2:03 pmChicago Midway
11h 48m
2 stops
YVR11:51 pmVancouver Intl
Delta
Dec 4
YVR12:13 pmVancouver Intl
9h 34m
2 stops
MDW11:47 pmChicago Midway
Dec 10
MDW1:50 pmChicago Midway
12h 09m
2 stops
YVR11:59 pmVancouver Intl

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets
WestJet
Jan 23
YVR5:00 pmVancouver Intl
16h 05m
2 stops
MDW11:05 amChicago Midway
Jan 25
MDW7:16 pmChicago Midway
31h 28m
3 stops
YVR12:44 amVancouver Intl
WestJet
Mar 27
YVR6:15 pmVancouver Intl
13h 40m
2 stops
MDW9:55 amChicago Midway
Mar 31
MDW9:30 amChicago Midway
13h 38m
2 stops
YVR9:08 pmVancouver Intl
WestJet
Feb 13
YVR9:15 pmVancouver Intl
10h 51m
2 stops
MDW10:06 amChicago Midway
Feb 18
MDW10:53 amChicago Midway
31h 00m
2 stops
YVR3:53 pmVancouver Intl

momondo Fare Finder

 
Customize your flight search to find flights from Vancouver 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 November 26, 2025.
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

Thu 3/5

5:00 pm-10:05 am

1 stop15h 05m

Chicago Midway

Tue 3/10

6:00 am-10:40 pm

2 stops18h 40m

$307

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/12

11:00 pm-11:33 am

1 stop10h 33m

Chicago Midway

Sun 4/19

11:00 am-10:38 pm

2 stops13h 38m

$319

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/12

11:00 pm-11:33 am

1 stop10h 33m

Chicago Midway

Sun 4/19

4:15 pm-12:57 pm

1 stop22h 42m

$322

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/12

11:00 pm-11:33 am

1 stop10h 33m

Chicago Midway

Sun 4/19

11:00 am-10:38 pm

2 stops13h 38m

$324

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/12

11:00 pm-11:33 am

1 stop10h 33m

Chicago Midway

Wed 4/15

4:15 pm-11:29 am

1 stop21h 14m

$333

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/15

5:00 pm-10:05 am

1 stop15h 05m

Chicago Midway

Sun 4/19

11:00 am-9:08 pm

1 stop12h 08m

$335

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 12/7

11:00 pm-8:46 am

1 stop31h 46m

Chicago Midway

Wed 12/10

2:49 pm-12:10 am

2 stops11h 21m

$338

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 4/11

12:10 am-3:20 pm

1 stop13h 10m

Chicago Midway

Wed 4/15

4:15 pm-11:50 am

1 stop21h 35m

$344

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 4/11

12:10 am-3:20 pm

1 stop13h 10m

Chicago Midway

Sun 4/19

11:00 am-10:38 pm

2 stops13h 38m

$346

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 4/11

12:10 am-3:20 pm

1 stop13h 10m

Chicago Midway

Sun 4/19

11:00 am-9:08 pm

1 stop12h 08m

$348

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 Vancouver 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

What is the cheapest airline that flies from Vancouver to Chicago Midway?

Porter Airlines is the most popular carrier operating from Vancouver to Chicago Midway

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

10h 33m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 10h 33m
There are no direct flights from Vancouver to Chicago Midway Airport. There are no popular flight routes from Vancouver to Chicago Midway Airport.
  • How far is Vancouver to Chicago Midway by plane?

    The straight-line distance from Vancouver to Chicago Midway is 1768.9 mi. 8h 51m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Vancouver to Chicago Midway Airport?

    Prices for flights from Vancouver to Chicago Midway Airport are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 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
Portage
Lansing
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 Vancouver to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Vancouver to Chicago for you.

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

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

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Vancouver.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Vancouver and alert you when they change.

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1 adult
Fri 12/26
Fri 1/2

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