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Cheap flights from Vancouver to Chicago from $156

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 2/25. 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 - 8:07 pm
YVR
-
MDW
19h 07m
1 stop
Multiple Airlines Logo
2:56 pm - 11:12 am
MDW
-
YVR
22h 16m
1 stop
$343Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
11:00 pm - 8:07 pm
YVR
-
MDW
19h 07m
1 stop
Multiple Airlines Logo
2:56 pm - 11:12 am
MDW
-
YVR
22h 16m
1 stop
$345Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
12:55 pm - 10:05 am
YVR
-
MDW
19h 10m
1 stop
Multiple Airlines Logo
11:00 am - 8:43 pm
MDW
-
YVR
11h 43m
2 stops
$393Multiple Airlines
Thu, Mar 5 - Thu, Mar 12
Multiple Airlines Logo
12:55 pm - 10:05 am
YVR
-
MDW
19h 10m
1 stop
Multiple Airlines Logo
11:00 am - 12:38 am
MDW
-
YVR
15h 38m
1 stop
$428Multiple Airlines
Thu, Mar 5 - Thu, Mar 12
Multiple Airlines Logo
12:05 pm - 10:41 pm
YVR
-
MDW
8h 36m
1 stop
Multiple Airlines Logo
9:51 pm - 11:25 pm
MDW
-
YVR
27h 34m
2 stops
$429Multiple Airlines
Sat, Mar 7 - Mon, Mar 9
Multiple Airlines Logo
12:05 pm - 10:41 pm
YVR
-
MDW
8h 36m
1 stop
Multiple Airlines Logo
9:51 pm - 4:07 pm
MDW
-
YVR
20h 16m
2 stops
$432Multiple Airlines
Sat, Mar 7 - Mon, Mar 9
Multiple Airlines Logo
11:00 pm - 8:07 pm
YVR
-
MDW
19h 07m
1 stop
Multiple Airlines Logo
11:00 am - 8:43 pm
MDW
-
YVR
11h 43m
2 stops
$448Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Delta Logo
6:20 am - 5:37 pm
YVR
-
MDW
9h 17m
2 stops
Delta Logo
1:10 pm - 11:59 pm
MDW
-
YVR
12h 49m
2 stops
$449Delta
Thu, Mar 5 - Tue, Mar 10
Multiple Airlines Logo
4:15 pm - 10:05 am
YVR
-
MDW
15h 50m
1 stop
Multiple Airlines Logo
11:00 am - 12:10 am
MDW
-
YVR
15h 10m
3 stops
$459Multiple Airlines
Thu, Mar 5 - Thu, Mar 12
Delta Logo
7:37 pm - 8:54 am
YVR
-
MDW
11h 17m
2 stops
Delta Logo
1:29 pm - 11:59 pm
MDW
-
YVR
12h 30m
2 stops
$467Delta
Mon, Mar 2 - Wed, Mar 4

Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets
Delta
Mar 5
YVR6:20 amVancouver Intl
9h 17m
2 stops
MDW5:37 pmChicago Midway
Mar 10
MDW1:10 pmChicago Midway
12h 49m
2 stops
YVR11:59 pmVancouver Intl
$449
Delta
Mar 2
YVR7:37 pmVancouver Intl
11h 17m
2 stops
MDW8:54 amChicago Midway
Mar 4
MDW1:29 pmChicago Midway
12h 30m
2 stops
YVR11:59 pmVancouver Intl
$467
Delta
Mar 2
YVR7:37 pmVancouver Intl
11h 17m
2 stops
MDW8:54 amChicago Midway
Mar 4
MDW9:34 amChicago Midway
16h 25m
2 stops
YVR11:59 pmVancouver Intl
$468

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets
WestJet
Apr 25
YVR6:00 amVancouver Intl
25h 56m
2 stops
MDW9:56 amChicago Midway
Apr 28
MDW9:31 amChicago Midway
17h 14m
2 stops
YVR12:45 amVancouver Intl
$562
WestJet
Apr 25
YVR5:00 pmVancouver Intl
13h 47m
2 stops
MDW8:47 amChicago Midway
Apr 28
MDW9:27 amChicago Midway
13h 23m
2 stops
YVR8:50 pmVancouver Intl
$565
WestJet
May 28
YVR5:30 pmVancouver Intl
13h 13m
2 stops
MDW8:43 amChicago Midway
Jun 2
MDW9:22 amChicago Midway
11h 08m
2 stops
YVR6:30 pmVancouver Intl
$569

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 February 4, 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

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/8

11:00 pm-8:07 pm

1 stop19h 07m

Chicago Midway

Sun 4/12

2:56 pm-11:12 am

1 stop22h 16m

$343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/8

11:00 pm-8:07 pm

1 stop19h 07m

Chicago Midway

Sun 4/12

2:56 pm-11:12 am

1 stop22h 16m

$345

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

12:55 pm-10:05 am

1 stop19h 10m

Chicago Midway

Thu 3/12

11:00 am-8:43 pm

2 stops11h 43m

$393

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

12:55 pm-10:05 am

1 stop19h 10m

Chicago Midway

Thu 3/12

11:00 am-12:38 am

1 stop15h 38m

$428

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 3/7

12:05 pm-10:41 pm

1 stop8h 36m

Chicago Midway

Mon 3/9

9:51 pm-11:25 pm

2 stops27h 34m

$429

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 3/7

12:05 pm-10:41 pm

1 stop8h 36m

Chicago Midway

Mon 3/9

9:51 pm-4:07 pm

2 stops20h 16m

$432

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/8

11:00 pm-8:07 pm

1 stop19h 07m

Chicago Midway

Sun 4/12

11:00 am-8:43 pm

2 stops11h 43m

$448

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

6:20 am-5:37 pm

2 stops9h 17m

Chicago Midway

Tue 3/10

1:10 pm-11:59 pm

2 stops12h 49m

$449

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

4:15 pm-10:05 am

1 stop15h 50m

Chicago Midway

Thu 3/12

11:00 am-12:10 am

3 stops15h 10m

$459

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 3/2

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Wed 3/4

1:29 pm-11:59 pm

2 stops12h 30m

$467

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 29m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 8h 29m
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

  • How far is Vancouver to Chicago Midway by plane?

    The straight-line distance from Vancouver to Chicago Midway is 1768.9 mi. 8h 29m 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.

  • How do I get Price Alerts for flights from Vancouver to Chicago Midway Airport?

    Confirm your travel details to search for the latest offers for flights from Vancouver to Chicago Midway Airport. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

  • How can I save money on flights from Vancouver to Chicago Midway Airport with momondo?

    Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

  • How does momondo find its flight prices?

    momondo shows deals across 700+ competitors all at once. momondo is active in 30 international markets, so you can have access to a wide range of options from airlines and OTAs alike.

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
Munster
Crown Point
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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