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Cheap flights from Vancouver Intl Airport to Chicago from $218

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 9/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Vancouver Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:05 am - 6:24 pm
YVR
-
MDW
10h 19m
1 stop
WestJet Logo
2:05 pm - 8:31 pm
MDW
-
YVR
8h 26m
1 stop
$406WestJet
Fri, Sep 11 - Mon, Sep 14
Delta Logo
6:00 am - 6:19 pm
YVR
-
MDW
10h 19m
1 stop
Delta Logo
2:00 pm - 8:26 pm
MDW
-
YVR
8h 26m
1 stop
$411Delta
Fri, Sep 18 - Wed, Sep 23
Delta Logo
6:00 am - 6:19 pm
YVR
-
MDW
10h 19m
1 stop
Delta Logo
2:00 pm - 8:26 pm
MDW
-
YVR
8h 26m
1 stop
$412Delta
Fri, Sep 11 - Mon, Sep 14
Delta Logo
6:00 am - 6:19 pm
YVR
-
MDW
10h 19m
1 stop
Delta Logo
2:00 pm - 8:26 pm
MDW
-
YVR
8h 26m
1 stop
$419Delta
Fri, Sep 18 - Wed, Sep 23
Delta Logo
6:15 am - 4:50 pm
YVR
-
MDW
8h 35m
1 stop
Delta Logo
12:30 pm - 8:32 pm
MDW
-
YVR
10h 02m
1 stop
$427Delta
Sat, Oct 10 - Sun, Oct 18
Delta Logo
6:15 am - 4:50 pm
YVR
-
MDW
8h 35m
1 stop
Delta Logo
12:30 pm - 8:32 pm
MDW
-
YVR
10h 02m
1 stop
$429Delta
Sun, Oct 11 - Sun, Oct 18
Delta Logo
5:45 pm - 8:48 am
YVR
-
MDW
13h 03m
2 stops
Delta Logo
2:00 pm - 8:26 pm
MDW
-
YVR
8h 26m
1 stop
$436Delta
Fri, Sep 11 - Mon, Sep 14
Multiple Airlines Logo
10:55 pm - 10:58 am
YVR
-
MDW
10h 03m
1 stop
Multiple Airlines Logo
7:25 am - 7:10 pm
MDW
-
YVR
13h 45m
2 stops
$440Multiple Airlines
Tue, Sep 22 - Tue, Sep 29
Delta Logo
5:45 pm - 8:48 am
YVR
-
MDW
13h 03m
2 stops
Delta Logo
9:24 am - 6:40 pm
MDW
-
YVR
11h 16m
2 stops
$460Delta
Fri, Sep 11 - Mon, Sep 14
Multiple Airlines Logo
10:55 pm - 10:58 am
YVR
-
MDW
10h 03m
1 stop
Multiple Airlines Logo
7:25 am - 7:10 pm
MDW
-
YVR
13h 45m
2 stops
$471Multiple Airlines
Mon, Sep 28 - Mon, Oct 5

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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
Sep 18
YVR6:00 amVancouver Intl
10h 19m
1 stop
MDW6:19 pmChicago Midway
Sep 23
MDW2:00 pmChicago Midway
8h 26m
1 stop
YVR8:26 pmVancouver Intl
$411
Delta
Sep 11
YVR6:00 amVancouver Intl
10h 19m
1 stop
MDW6:19 pmChicago Midway
Sep 14
MDW2:00 pmChicago Midway
8h 26m
1 stop
YVR8:26 pmVancouver Intl
$412
Delta
Sep 18
YVR6:00 amVancouver Intl
10h 19m
1 stop
MDW6:19 pmChicago Midway
Sep 23
MDW2:00 pmChicago Midway
8h 26m
1 stop
YVR8:26 pmVancouver Intl
$419

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
Sep 11
YVR6:05 amVancouver Intl
10h 19m
1 stop
MDW6:24 pmChicago Midway
Sep 14
MDW2:05 pmChicago Midway
8h 26m
1 stop
YVR8:31 pmVancouver Intl
$406
WestJet
Sep 28
YVR6:05 amVancouver Intl
10h 19m
1 stop
MDW6:24 pmChicago Midway
Oct 5
MDW2:05 pmChicago Midway
8h 26m
1 stop
YVR8:31 pmVancouver Intl
$492
WestJet
Sep 27
YVR6:05 amVancouver Intl
10h 19m
1 stop
MDW6:24 pmChicago Midway
Sep 30
MDW2:05 pmChicago Midway
8h 26m
1 stop
YVR8:31 pmVancouver Intl
$525

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 June 25, 2026.
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

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/11

6:05 am-6:24 pm

1 stop10h 19m

Chicago Midway

Mon 9/14

2:05 pm-8:31 pm

1 stop8h 26m

$406

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/18

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Wed 9/23

2:00 pm-8:26 pm

1 stop8h 26m

$411

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/11

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Mon 9/14

2:00 pm-8:26 pm

1 stop8h 26m

$412

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/18

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Wed 9/23

2:00 pm-8:26 pm

1 stop8h 26m

$419
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

6:15 am-4:50 pm

1 stop8h 35m

Chicago Midway

Sun 10/18

12:30 pm-8:32 pm

1 stop10h 02m

$427

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 10/11

6:15 am-4:50 pm

1 stop8h 35m

Chicago Midway

Sun 10/18

12:30 pm-8:32 pm

1 stop10h 02m

$429

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/11

5:45 pm-8:48 am

2 stops13h 03m

Chicago Midway

Mon 9/14

2:00 pm-8:26 pm

1 stop8h 26m

$436

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 9/22

10:55 pm-10:58 am

1 stop10h 03m

Chicago Midway

Tue 9/29

7:25 am-7:10 pm

2 stops13h 45m

$440

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 9/11

5:45 pm-8:48 am

2 stops13h 03m

Chicago Midway

Mon 9/14

9:24 am-6:40 pm

2 stops11h 16m

$460

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 9/28

10:55 pm-10:58 am

1 stop10h 03m

Chicago Midway

Mon 10/5

7:25 am-7:10 pm

2 stops13h 45m

$471

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 is the most popular carrier 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

Fastest flight time

10h 01m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 10h 01m
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.
Search flight deals

Frequently asked questions about flying from Vancouver Intl Airport to Chicago Midway Airport

  • 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 10h 01m.

  • 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
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Hammond
Portage
Benton Harbor
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Valparaiso
Schererville
Munster
Crown Point
Chesterton
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Porter
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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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