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Cheap flights from Vancouver to Chicago from $112

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 12/7. 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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Cheap round-trip flights

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Multiple Airlines Logo
11:00 pm - 8:46 amYVR-MDW
31h 46m1 stop
Multiple Airlines Logo
6:15 am - 11:12 amMDW-YVR
30h 57m1 stop
$204Multiple Airlines
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Sun, Dec 7 - Sun, Dec 14
Multiple Airlines Logo
11:00 pm - 9:52 amYVR-MDW
8h 52m1 stop
Multiple Airlines Logo
8:42 pm - 11:12 amMDW-YVR
16h 30m1 stop
$217Multiple Airlines
Find Deal
Sun, Dec 7 - Fri, Dec 12
Multiple Airlines Logo
9:15 pm - 1:59 pmYVR-MDW
14h 44m2 stops
Multiple Airlines Logo
8:42 pm - 11:12 amMDW-YVR
16h 30m1 stop
$221Multiple Airlines
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Fri, Dec 5 - Fri, Dec 12
Multiple Airlines Logo
11:00 pm - 10:43 pmYVR-MDW
21h 43m1 stop
Multiple Airlines Logo
6:05 am - 11:12 amMDW-YVR
31h 07m1 stop
$224Multiple Airlines
Find Deal
Sun, Nov 23 - Wed, Nov 26
Multiple Airlines Logo
11:00 pm - 10:43 pmYVR-MDW
21h 43m1 stop
Multiple Airlines Logo
6:05 am - 10:45 pmMDW-YVR
18h 40m2 stops
$237Multiple Airlines
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Sun, Nov 23 - Wed, Nov 26
Multiple Airlines Logo
11:00 pm - 10:43 pmYVR-MDW
21h 43m1 stop
Multiple Airlines Logo
6:05 am - 10:45 pmMDW-YVR
18h 40m2 stops
$239Multiple Airlines
Find Deal
Sun, Nov 23 - Tue, Nov 25
Multiple Airlines Logo
3:40 pm - 8:46 amYVR-MDW
15h 06m2 stops
Multiple Airlines Logo
8:42 pm - 11:12 amMDW-YVR
16h 30m1 stop
$281Multiple Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
Multiple Airlines Logo
10:30 pm - 3:20 pmYVR-MDW
14h 50m1 stop
Multiple Airlines Logo
6:15 am - 10:45 pmMDW-YVR
18h 30m2 stops
$317Multiple Airlines
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Thu, Dec 4 - Mon, Dec 8
Multiple Airlines Logo
10:55 pm - 3:20 pmYVR-MDW
14h 25m1 stop
Multiple Airlines Logo
7:23 pm - 10:45 pmMDW-YVR
29h 22m2 stops
$337Multiple Airlines
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Thu, Nov 27 - Thu, Dec 4
Delta Logo
7:35 pm - 9:19 amYVR-MDW
11h 44m2 stops
Delta Logo
1:50 pm - 11:59 pmMDW-YVR
12h 09m2 stops
$348Delta
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Tue, Dec 2 - Sat, Dec 13

Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets
Delta
Dec 2
YVR7:35 pmVancouver Intl
11h 44m
2 stops
MDW9:19 amChicago Midway
Dec 10
MDW9:59 amChicago Midway
10h 45m
2 stops
YVR6:44 pmVancouver Intl
$348
Find similar
Delta
Dec 8
YVR7:36 pmVancouver Intl
11h 43m
2 stops
MDW9:19 amChicago Midway
Dec 16
MDW9:59 amChicago Midway
13h 05m
2 stops
YVR9:04 pmVancouver Intl
$355
Find similar
Delta
Feb 5
YVR7:37 pmVancouver Intl
11h 17m
2 stops
MDW8:54 amChicago Midway
Feb 15
MDW9:50 amChicago Midway
13h 04m
2 stops
YVR8:54 pmVancouver Intl
$362
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Porter Airlines flights from Vancouver to Chicago Midway Airport

Our best Porter Airlines deals on Vancouver to Chicago Midway Airport flight tickets
Porter Airlines
Nov 27
YVR12:20 pmVancouver Intl
19h 45m
2 stops
MDW10:05 amChicago Midway
Dec 1
MDW11:00 amChicago Midway
12h 23m
2 stops
YVR9:23 pmVancouver Intl
$436
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Porter Airlines
Nov 27
YVR12:20 pmVancouver Intl
19h 45m
2 stops
MDW10:05 amChicago Midway
Nov 30
MDW11:00 amChicago Midway
11h 43m
2 stops
YVR8:43 pmVancouver Intl
$463
Find similar
Porter Airlines
Nov 27
YVR12:20 pmVancouver Intl
19h 45m
2 stops
MDW10:05 amChicago Midway
Dec 4
MDW11:00 amChicago Midway
11h 46m
2 stops
YVR8:46 pmVancouver Intl
$493
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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 13, 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

Sun 12/7

11:00 pm-8:46 am

1 stop31h 46m

Chicago Midway

Sun 12/14

6:15 am-11:12 am

1 stop30h 57m

$204

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 12/7

11:00 pm-9:52 am

1 stop8h 52m

Chicago Midway

Fri 12/12

8:42 pm-11:12 am

1 stop16h 30m

$217

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 12/5

9:15 pm-1:59 pm

2 stops14h 44m

Chicago Midway

Fri 12/12

8:42 pm-11:12 am

1 stop16h 30m

$221

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 11/23

11:00 pm-10:43 pm

1 stop21h 43m

Chicago Midway

Wed 11/26

6:05 am-11:12 am

1 stop31h 07m

$224

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 11/23

11:00 pm-10:43 pm

1 stop21h 43m

Chicago Midway

Wed 11/26

6:05 am-10:45 pm

2 stops18h 40m

$237

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 11/23

11:00 pm-10:43 pm

1 stop21h 43m

Chicago Midway

Tue 11/25

6:05 am-10:45 pm

2 stops18h 40m

$239

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 12/8

3:40 pm-8:46 am

2 stops15h 06m

Chicago Midway

Fri 12/12

8:42 pm-11:12 am

1 stop16h 30m

$281

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 12/4

10:30 pm-3:20 pm

1 stop14h 50m

Chicago Midway

Mon 12/8

6:15 am-10:45 pm

2 stops18h 30m

$317

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 11/27

10:55 pm-3:20 pm

1 stop14h 25m

Chicago Midway

Thu 12/4

7:23 pm-10:45 pm

2 stops29h 22m

$337

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 12/2

7:35 pm-9:19 am

2 stops11h 44m

Chicago Midway

Sat 12/13

1:50 pm-11:59 pm

2 stops12h 09m

$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?

Delta, WestJet, and Porter Airlines are the most popular carriers 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

Direct flights

None
There are no direct flights from Vancouver to Chicago Midway Airport. There are no popular flight routes from Vancouver to Chicago Midway Airport.
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  • How far is Vancouver to Chicago Midway by plane?

    The straight-line distance from Vancouver to Chicago Midway is 1768.9 mi. 8h 52m 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.

An easier way to manage your Chicago Midway Airport trip

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