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.

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.

$116 Cheap Flights from Vancouver to Chicago Midway Airport in 2025/26

1 adult

0 bags

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Find the cheapest flights from Vancouver to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:00 pm - 10:13 pm

YVR

MDW

21h 13m1 stop

11:05 am - 12:15 am

MDW

YVR

15h 10m2 stops

$311Multiple Airlines

Fri, Jan 16 - Sun, Jan 18

5:00 pm - 10:10 am

YVR

MDW

15h 10m1 stop

1:20 pm - 11:12 am

MDW

YVR

23h 52m1 stop

$322Multiple Airlines

Thu, Jan 15 - Wed, Jan 21

5:00 pm - 10:10 am

YVR

MDW

15h 10m1 stop

1:20 pm - 11:12 am

MDW

YVR

23h 52m1 stop

$325Multiple Airlines

Thu, Jan 15 - Wed, Jan 21

7:37 pm - 8:52 am

YVR

MDW

11h 15m2 stops

9:50 am - 6:44 pm

MDW

YVR

10h 54m2 stops

$355Delta

Thu, Jan 15 - Wed, Jan 21

7:37 pm - 8:52 am

YVR

MDW

11h 15m2 stops

9:33 am - 11:59 pm

MDW

YVR

16h 26m2 stops

$356Delta

Thu, Jan 29 - Sun, Feb 1

7:35 pm - 8:53 am

YVR

MDW

11h 18m2 stops

9:30 am - 8:55 pm

MDW

YVR

13h 25m2 stops

$374Delta

Mon, Mar 30 - Sat, Apr 4

7:37 pm - 8:52 am

YVR

MDW

11h 15m2 stops

1:26 pm - 11:59 pm

MDW

YVR

12h 33m2 stops

$375Delta

Thu, Jan 29 - Mon, Feb 2

7:37 pm - 8:52 am

YVR

MDW

11h 15m2 stops

9:33 am - 11:59 pm

MDW

YVR

16h 26m2 stops

$386Delta

Thu, Jan 29 - Sun, Feb 1

7:37 pm - 8:52 am

YVR

MDW

11h 15m2 stops

9:32 am - 8:54 pm

MDW

YVR

13h 22m2 stops

$395Delta

Thu, Jan 15 - Wed, Jan 21

7:37 pm - 8:54 am

YVR

MDW

11h 17m2 stops

1:28 pm - 11:59 pm

MDW

YVR

12h 31m2 stops

$405Delta

Tue, Feb 24 - Fri, Feb 27

Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets

Delta

Jan 15

YVR7:37 pmVancouver Intl

11h 15m

2 stops

MDW8:52 amChicago Midway

Jan 21

MDW9:50 amChicago Midway

10h 54m

2 stops

YVR6:44 pmVancouver Intl

$355

Find similar

Delta

Jan 29

YVR7:37 pmVancouver Intl

11h 15m

2 stops

MDW8:52 amChicago Midway

Feb 1

MDW9:33 amChicago Midway

16h 26m

2 stops

YVR11:59 pmVancouver Intl

$356

Find similar

Delta

Mar 30

YVR7:35 pmVancouver Intl

11h 18m

2 stops

MDW8:53 amChicago Midway

Apr 4

MDW9:30 amChicago Midway

13h 25m

2 stops

YVR8:55 pmVancouver Intl

$374

Find similar

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets

WestJet

Mar 27

YVR6:00 amVancouver Intl

24h 53m

2 stops

MDW8:53 amChicago Midway

Mar 31

MDW7:20 pmChicago Midway

27h 48m

2 stops

YVR9:08 pmVancouver Intl

$468

Find similar

WestJet

Mar 27

YVR6:00 amVancouver Intl

24h 53m

2 stops

MDW8:53 amChicago Midway

Mar 31

MDW7:20 pmChicago Midway

27h 48m

2 stops

YVR9:08 pmVancouver Intl

$481

Find similar

WestJet

Mar 31

YVR7:45 pmVancouver Intl

12h 11m

2 stops

MDW9:56 amChicago Midway

Apr 5

MDW9:30 amChicago Midway

13h 38m

2 stops

YVR9:08 pmVancouver Intl

$590

Find similar

momondo Fare Finder

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

Fri 1/16

11:00 pm-10:13 pm

1 stop21h 13m

Chicago Midway

Sun 1/18

11:05 am-12:15 am

2 stops15h 10m

$311

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/15

5:00 pm-10:10 am

1 stop15h 10m

Chicago Midway

Wed 1/21

1:20 pm-11:12 am

1 stop23h 52m

$322

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/15

5:00 pm-10:10 am

1 stop15h 10m

Chicago Midway

Wed 1/21

1:20 pm-11:12 am

1 stop23h 52m

$325

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/15

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Wed 1/21

9:50 am-6:44 pm

2 stops10h 54m

$355

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/29

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Sun 2/1

9:33 am-11:59 pm

2 stops16h 26m

$356

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 3/30

7:35 pm-8:53 am

2 stops11h 18m

Chicago Midway

Sat 4/4

9:30 am-8:55 pm

2 stops13h 25m

$374

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/29

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Mon 2/2

1:26 pm-11:59 pm

2 stops12h 33m

$375

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/29

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Sun 2/1

9:33 am-11:59 pm

2 stops16h 26m

$386

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/15

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Wed 1/21

9:32 am-8:54 pm

2 stops13h 22m

$395

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 2/24

7:37 pm-8:54 am

2 stops11h 17m

Chicago Midway

Fri 2/27

1:28 pm-11:59 pm

2 stops12h 31m

$405

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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	9h 17m
Direct flights	None

The fastest flight from Vancouver to Chicago Midway Airport takes 9h 17m

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. 9h 17m 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.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

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.