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Cheap flights from Vancouver to Chicago from $217

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 9/1. 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 4:39 pm
YVR
-
MDW
8h 39m
1 stop
Delta Logo
12:28 pm - 11:08 pm
MDW
-
YVR
12h 40m
2 stops
$376Delta
Sat, Oct 10 - Tue, Oct 13
Delta Logo
6:00 am - 4:39 pm
YVR
-
MDW
8h 39m
1 stop
Delta Logo
12:28 pm - 11:08 pm
MDW
-
YVR
12h 40m
2 stops
$377Delta
Sat, Oct 10 - Tue, Oct 13
Delta Logo
7:30 pm - 8:48 am
YVR
-
MDW
11h 18m
2 stops
Delta Logo
6:05 am - 10:34 pm
MDW
-
YVR
18h 29m
2 stops
$391Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
7:30 pm - 8:48 am
YVR
-
MDW
11h 18m
2 stops
Delta Logo
10:48 am - 10:34 pm
MDW
-
YVR
13h 46m
2 stops
$392Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
6:00 am - 6:19 pm
YVR
-
MDW
10h 19m
1 stop
Delta Logo
1:19 pm - 10:59 pm
MDW
-
YVR
11h 40m
2 stops
$403Delta
Tue, Sep 29 - Mon, Oct 5
Delta Logo
6:00 am - 6:19 pm
YVR
-
MDW
10h 19m
1 stop
Delta Logo
1:19 pm - 10:59 pm
MDW
-
YVR
11h 40m
2 stops
$417Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
7:30 pm - 8:48 am
YVR
-
MDW
11h 18m
2 stops
Delta Logo
9:29 am - 10:59 pm
MDW
-
YVR
15h 30m
2 stops
$418Delta
Thu, Oct 1 - Mon, Oct 5
Delta Logo
6:00 am - 6:01 pm
YVR
-
MDW
10h 01m
1 stop
Delta Logo
9:59 am - 7:10 pm
MDW
-
YVR
11h 11m
2 stops
$421Delta
Tue, Aug 25 - Tue, Sep 1
WestJet Logo
6:05 am - 6:24 pm
YVR
-
MDW
10h 19m
1 stop
WestJet Logo
12:33 pm - 8:38 pm
MDW
-
YVR
10h 05m
1 stop
$435WestJet
Wed, Sep 30 - Tue, Oct 6
Delta Logo
7:35 pm - 9:17 am
YVR
-
MDW
11h 42m
2 stops
Delta Logo
9:59 am - 7:10 pm
MDW
-
YVR
11h 11m
2 stops
$436Delta
Tue, Aug 25 - Mon, Aug 31

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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
Jul 20
YVR9:55 pmVancouver Intl
14h 40m
1 stop
MDW2:35 pmChicago Midway
Jul 22
MDW10:25 amChicago Midway
12h 39m
1 stop
YVR9:04 pmVancouver Intl
$684
Porter Airlines
Jul 20
YVR10:00 pmVancouver Intl
14h 35m
2 stops
MDW2:35 pmChicago Midway
Jul 22
MDW10:25 amChicago Midway
13h 10m
2 stops
YVR9:35 pmVancouver Intl
$717
Porter Airlines
Jul 19
YVR10:00 pmVancouver Intl
33h 40m
2 stops
MDW9:40 amChicago Midway
Jul 22
MDW3:20 pmChicago Midway
32h 15m
2 stops
YVR9:35 pmVancouver Intl
$767

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets
WestJet
Sep 30
YVR6:05 amVancouver Intl
10h 19m
1 stop
MDW6:24 pmChicago Midway
Oct 6
MDW12:33 pmChicago Midway
10h 05m
1 stop
YVR8:38 pmVancouver Intl
$435
WestJet
Sep 18
YVR6:05 amVancouver Intl
10h 19m
1 stop
MDW6:24 pmChicago Midway
Sep 23
MDW2:05 pmChicago Midway
8h 26m
1 stop
YVR8:31 pmVancouver Intl
$458
WestJet
Sep 3
YVR6:05 amVancouver Intl
10h 01m
1 stop
MDW6:06 pmChicago Midway
Sep 8
MDW2:05 pmChicago Midway
8h 26m
1 stop
YVR8:31 pmVancouver Intl
$476

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 July 7, 2026.
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

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

6:00 am-4:39 pm

1 stop8h 39m

Chicago Midway

Tue 10/13

12:28 pm-11:08 pm

2 stops12h 40m

$376

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

6:00 am-4:39 pm

1 stop8h 39m

Chicago Midway

Tue 10/13

12:28 pm-11:08 pm

2 stops12h 40m

$377

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/1

7:30 pm-8:48 am

2 stops11h 18m

Chicago Midway

Mon 10/5

6:05 am-10:34 pm

2 stops18h 29m

$391

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/1

7:30 pm-8:48 am

2 stops11h 18m

Chicago Midway

Mon 10/5

10:48 am-10:34 pm

2 stops13h 46m

$392

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 9/29

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Mon 10/5

1:19 pm-10:59 pm

2 stops11h 40m

$403

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/1

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Mon 10/5

1:19 pm-10:59 pm

2 stops11h 40m

$417

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 10/1

7:30 pm-8:48 am

2 stops11h 18m

Chicago Midway

Mon 10/5

9:29 am-10:59 pm

2 stops15h 30m

$418

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 8/25

6:00 am-6:01 pm

1 stop10h 01m

Chicago Midway

Tue 9/1

9:59 am-7:10 pm

2 stops11h 11m

$421
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 9/30

6:05 am-6:24 pm

1 stop10h 19m

Chicago Midway

Tue 10/6

12:33 pm-8:38 pm

1 stop10h 05m

$435

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 8/25

7:35 pm-9:17 am

2 stops11h 42m

Chicago Midway

Mon 8/31

9:59 am-7:10 pm

2 stops11h 11m

$436

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 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

8h 39m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 8h 39m
There are no direct flights from Vancouver to Chicago Midway Airport. There are no popular flight routes from Vancouver to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying 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 1768.8 mi. 8h 39m 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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