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.

$94 Cheap Flights from Vancouver to Chicago Midway Airport in 2025/26

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

10:05 pm - 7:52 pmYVR-MDW

19h 47m2 stops

5:01 pm - 11:12 amMDW-YVR

20h 11m1 stop

$257Multiple Airlines

Find Deal

Thu, Feb 5 - Sun, Feb 8

9:10 am - 11:45 amYVR-MDW

24h 35m1 stop

9:15 am - 10:20 pmMDW-YVR

15h 05m2 stops

$259Multiple Airlines

Find Deal

Sat, Jan 10 - Mon, Jan 12

3:40 pm - 3:33 pmYVR-MDW

21h 53m2 stops

5:01 pm - 11:12 amMDW-YVR

20h 11m1 stop

$263Multiple Airlines

Find Deal

Thu, Jan 8 - Fri, Jan 30

4:45 pm - 11:45 amYVR-MDW

17h 00m2 stops

5:01 pm - 11:12 amMDW-YVR

20h 11m1 stop

$271Multiple Airlines

Find Deal

Sat, Jan 31 - Sun, Feb 8

3:40 pm - 8:46 amYVR-MDW

15h 06m2 stops

12:41 pm - 11:12 amMDW-YVR

24h 31m1 stop

$272Multiple Airlines

Find Deal

Tue, Dec 16 - Sun, Jan 11

5:30 pm - 11:45 amYVR-MDW

16h 15m2 stops

5:01 pm - 11:12 amMDW-YVR

20h 11m1 stop

$274Multiple Airlines

Find Deal

Thu, Jan 29 - Sun, Feb 1

7:37 pm - 5:29 pmYVR-MDW

19h 52m2 stops

1:49 pm - 10:47 amMDW-YVR

22h 58m2 stops

$313Delta

Find Deal

Thu, Jan 22 - Mon, Jan 26

7:30 am - 7:50 pmYVR-MDW

10h 20m1 stop

6:00 am - 10:40 pmMDW-YVR

18h 40m2 stops

$315Multiple Airlines

Find Deal

Mon, Mar 2 - Thu, Mar 5

10:05 pm - 10:10 amYVR-MDW

10h 05m1 stop

4:15 pm - 1:23 pmMDW-YVR

23h 08m3 stops

$331Multiple Airlines

Find Deal

Thu, Feb 5 - Sun, Feb 8

11:00 pm - 11:45 amYVR-MDW

10h 45m1 stop

6:20 am - 10:40 pmMDW-YVR

18h 20m2 stops

$338Multiple Airlines

Find Deal

Sun, Feb 1 - Thu, Feb 5

WestJet flights from Vancouver to Chicago Midway Airport

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

WestJet

Feb 14

YVR5:00 pmVancouver Intl

16h 03m

2 stops

MDW11:03 amChicago Midway

Feb 22

MDW10:53 amChicago Midway

12h 15m

2 stops

YVR9:08 pmVancouver Intl

$544

Find similar

WestJet

Mar 27

YVR9:15 pmVancouver Intl

10h 40m

2 stops

MDW9:55 amChicago Midway

Mar 31

MDW9:30 amChicago Midway

13h 38m

2 stops

YVR9:08 pmVancouver Intl

$561

Find similar

WestJet

Feb 14

YVR5:00 pmVancouver Intl

16h 03m

2 stops

MDW11:03 amChicago Midway

Feb 22

MDW10:53 amChicago Midway

12h 15m

2 stops

YVR9:08 pmVancouver Intl

$563

Find similar

Delta flights from Vancouver to Chicago Midway Airport

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

Delta

Jan 22

YVR7:37 pmVancouver Intl

19h 52m

2 stops

MDW5:29 pmChicago Midway

Jan 26

MDW1:49 pmChicago Midway

22h 58m

2 stops

YVR10:47 amVancouver Intl

$313

Find similar

Delta

Jan 24

YVR7:37 pmVancouver Intl

12h 16m

2 stops

MDW9:53 amChicago Midway

Jan 28

MDW9:50 amChicago Midway

10h 54m

2 stops

YVR6:44 pmVancouver Intl

$349

Find similar

Delta

Mar 5

YVR6:20 amVancouver Intl

9h 17m

2 stops

MDW5:37 pmChicago Midway

Mar 10

MDW9:32 amChicago Midway

13h 22m

2 stops

YVR8:54 pmVancouver Intl

$357

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

Thu 2/5

10:05 pm-7:52 pm

2 stops19h 47m

Chicago Midway

Sun 2/8

5:01 pm-11:12 am

1 stop20h 11m

$257

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 1/10

9:10 am-11:45 am

1 stop24h 35m

Chicago Midway

Mon 1/12

9:15 am-10:20 pm

2 stops15h 05m

$259

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/8

3:40 pm-3:33 pm

2 stops21h 53m

Chicago Midway

Fri 1/30

5:01 pm-11:12 am

1 stop20h 11m

$263

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 1/31

4:45 pm-11:45 am

2 stops17h 00m

Chicago Midway

Sun 2/8

5:01 pm-11:12 am

1 stop20h 11m

$271

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 12/16

3:40 pm-8:46 am

2 stops15h 06m

Chicago Midway

Sun 1/11

12:41 pm-11:12 am

1 stop24h 31m

$272

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/29

5:30 pm-11:45 am

2 stops16h 15m

Chicago Midway

Sun 2/1

5:01 pm-11:12 am

1 stop20h 11m

$274

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/22

7:37 pm-5:29 pm

2 stops19h 52m

Chicago Midway

Mon 1/26

1:49 pm-10:47 am

2 stops22h 58m

$313

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 3/2

7:30 am-7:50 pm

1 stop10h 20m

Chicago Midway

Thu 3/5

6:00 am-10:40 pm

2 stops18h 40m

$315

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 2/5

10:05 pm-10:10 am

1 stop10h 05m

Chicago Midway

Sun 2/8

4:15 pm-1:23 pm

3 stops23h 08m

$331

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 2/1

11:00 pm-11:45 am

1 stop10h 45m

Chicago Midway

Thu 2/5

6:20 am-10:40 pm

2 stops18h 20m

$338

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 50m
Direct flights	None

The fastest flight from Vancouver to Chicago Midway Airport takes 9h 50m

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 53m 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

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. 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.