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Cheap flights from Vancouver Intl Airport to Chicago from $113

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 Intl Airport to Chicago departing on 11/26. 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
11:00 pm - 10:12 pmYVR-MDW
21h 12m1 stop
Multiple Airlines Logo
7:23 pm - 3:45 pmMDW-YVR
22h 22m2 stops
$205Multiple Airlines
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Sun, Dec 7 - Thu, Dec 11
Multiple Airlines Logo
11:00 pm - 9:52 amYVR-MDW
8h 52m1 stop
Multiple Airlines Logo
6:15 am - 10:45 pmMDW-YVR
18h 30m2 stops
$241Multiple Airlines
Find Deal
Sun, Dec 7 - Fri, Dec 12
Multiple Airlines Logo
11:00 pm - 6:39 pmYVR-MDW
17h 39m1 stop
Multiple Airlines Logo
1:56 pm - 2:45 pmMDW-YVR
26h 49m2 stops
$270Multiple Airlines
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Fri, Nov 14 - Tue, Nov 18
Multiple Airlines Logo
11:00 pm - 7:23 pmYVR-MDW
18h 23m1 stop
Multiple Airlines Logo
6:00 am - 10:45 pmMDW-YVR
18h 45m2 stops
$285Multiple Airlines
Find Deal
Wed, Jan 14 - Mon, Jan 26
Multiple Airlines Logo
11:00 pm - 9:52 amYVR-MDW
8h 52m1 stop
Multiple Airlines Logo
6:15 am - 4:31 pmMDW-YVR
12h 16m1 stop
$286Multiple Airlines
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Sun, Dec 7 - Fri, Dec 12
Delta Logo
7:37 pm - 8:54 amYVR-MDW
11h 17m2 stops
Delta Logo
9:34 am - 8:54 pmMDW-YVR
13h 20m2 stops
$426Delta
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Wed, Jan 14 - Sat, Jan 24
Delta Logo
11:00 pm - 9:52 amYVR-MDW
8h 52m1 stop
Delta Logo
1:15 pm - 10:37 pmMDW-YVR
11h 22m2 stops
$478Delta
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Wed, Nov 19 - Wed, Nov 26
Porter Airlines Logo
12:20 pm - 10:05 amYVR-MDW
19h 45m2 stops
Porter Airlines Logo
11:00 am - 9:23 pmMDW-YVR
12h 23m2 stops
$518Porter Airlines
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Sun, Nov 30 - Wed, Dec 3
WestJet Logo
11:00 pm - 9:56 amYVR-MDW
8h 56m1 stop
WestJet Logo
10:35 am - 9:08 pmMDW-YVR
12h 33m2 stops
$591WestJet
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Fri, Mar 27 - Tue, Mar 31
WestJet Logo
11:00 pm - 10:01 amYVR-MDW
9h 01m1 stop
WestJet Logo
9:50 am - 12:44 amMDW-YVR
16h 54m2 stops
$608WestJet
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Fri, Jan 23 - Sun, Jan 25

Delta flights from Vancouver Intl Airport to Chicago Midway Airport

Our best Delta deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
Delta
Jan 14
YVR7:37 pmVancouver Intl
11h 17m
2 stops
MDW8:54 amChicago Midway
Jan 24
MDW9:34 amChicago Midway
13h 20m
2 stops
YVR8:54 pmVancouver Intl
$426
Find similar
Delta
Nov 19
YVR11:00 pmVancouver Intl
8h 52m
1 stop
MDW9:52 amChicago Midway
Nov 26
MDW1:15 pmChicago Midway
11h 22m
2 stops
YVR10:37 pmVancouver Intl
$478
Find similar
Delta
Mar 27
YVR7:35 pmVancouver Intl
11h 19m
2 stops
MDW8:54 amChicago Midway
Mar 31
MDW1:00 pmChicago Midway
9h 52m
2 stops
YVR8:52 pmVancouver Intl
$492
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WestJet flights from Vancouver Intl Airport to Chicago Midway Airport

Our best WestJet deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
WestJet
Mar 27
YVR11:00 pmVancouver Intl
8h 56m
1 stop
MDW9:56 amChicago Midway
Mar 31
MDW10:35 amChicago Midway
12h 33m
2 stops
YVR9:08 pmVancouver Intl
$591
Find similar
WestJet
Jan 23
YVR11:00 pmVancouver Intl
9h 01m
1 stop
MDW10:01 amChicago Midway
Jan 25
MDW9:50 amChicago Midway
16h 54m
2 stops
YVR12:44 amVancouver Intl
$608
Find similar
WestJet
Dec 4
YVR6:45 pmVancouver Intl
13h 09m
2 stops
MDW9:54 amChicago Midway
Dec 6
MDW9:59 amChicago Midway
16h 45m
2 stops
YVR12:44 amVancouver Intl
$616
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momondo Fare Finder

 
Customize your flight search to find flights from Vancouver Intl Airport 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 2, 2025.
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

Sun 12/7

11:00 pm-10:12 pm

1 stop21h 12m

Chicago Midway

Thu 12/11

7:23 pm-3:45 pm

2 stops22h 22m

$205

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 12/7

11:00 pm-9:52 am

1 stop8h 52m

Chicago Midway

Fri 12/12

6:15 am-10:45 pm

2 stops18h 30m

$241

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 11/14

11:00 pm-6:39 pm

1 stop17h 39m

Chicago Midway

Tue 11/18

1:56 pm-2:45 pm

2 stops26h 49m

$270

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 1/14

11:00 pm-7:23 pm

1 stop18h 23m

Chicago Midway

Mon 1/26

6:00 am-10:45 pm

2 stops18h 45m

$285

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 12/7

11:00 pm-9:52 am

1 stop8h 52m

Chicago Midway

Fri 12/12

6:15 am-4:31 pm

1 stop12h 16m

$286

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 1/14

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Sat 1/24

9:34 am-8:54 pm

2 stops13h 20m

$426

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 11/19

11:00 pm-9:52 am

1 stop8h 52m

Chicago Midway

Wed 11/26

1:15 pm-10:37 pm

2 stops11h 22m

$478

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 11/30

12:20 pm-10:05 am

2 stops19h 45m

Chicago Midway

Wed 12/3

11:00 am-9:23 pm

2 stops12h 23m

$518

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 3/27

11:00 pm-9:56 am

1 stop8h 56m

Chicago Midway

Tue 3/31

10:35 am-9:08 pm

2 stops12h 33m

$591

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/23

11:00 pm-10:01 am

1 stop9h 01m

Chicago Midway

Sun 1/25

9:50 am-12:44 am

2 stops16h 54m

$608

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 Intl Airport 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 Intl to Chicago Midway?

Delta and WestJet are the most popular carriers operating from Vancouver Intl to Chicago Midway

When to book flights from Vancouver Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Vancouver Intl Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Vancouver Intl Airport to Chicago Midway Airport (YVR to MDW) flight deals and tips

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

Direct flights

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

    The distance between Vancouver Intl and Chicago Midway is about 1771.5 mi. A reasonable flight in good conditions will take 8h 51m.

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

    Prices for flights from Vancouver Intl Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Vancouver Intl Airport 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 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.

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. 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?

Of course. momondo tracks the price of Vancouver to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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