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.

$164 Cheap Flights from Vancouver to Chicago Midway Airport in 2026

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.

9:30 am - 10:02 pm

YVR

MDW

10h 32m

1 stop

6:00 am - 7:10 pm

MDW

YVR

15h 10m

2 stops

$374Multiple Airlines

Sat, May 23 - Tue, Jun 2

6:00 am - 6:33 pm

YVR

MDW

10h 33m

2 stops

1:59 pm - 8:39 pm

MDW

YVR

8h 40m

1 stop

$376Delta

Wed, May 27 - Mon, Jun 1

10:55 pm - 11:09 am

YVR

MDW

10h 14m

1 stop

6:00 am - 7:10 pm

MDW

YVR

15h 10m

2 stops

$378Multiple Airlines

Tue, May 26 - Tue, Jun 2

6:15 am - 4:50 pm

YVR

MDW

8h 35m

1 stop

12:30 pm - 8:32 pm

MDW

YVR

10h 02m

1 stop

$381Delta

Sat, Oct 10 - Tue, Oct 13

6:20 am - 5:56 pm

YVR

MDW

9h 36m

2 stops

1:22 pm - 10:35 pm

MDW

YVR

11h 13m

2 stops

$401Delta

Sat, May 23 - Fri, May 29

6:00 am - 5:56 pm

YVR

MDW

9h 56m

1 stop

9:23 am - 7:10 pm

MDW

YVR

11h 47m

2 stops

$407Delta

Thu, May 21 - Wed, Jun 3

5:15 pm - 8:49 am

YVR

MDW

13h 34m

2 stops

9:30 am - 8:32 pm

MDW

YVR

13h 02m

2 stops

$409Delta

Sat, Oct 10 - Tue, Oct 13

7:35 pm - 8:49 am

YVR

MDW

11h 14m

2 stops

12:30 pm - 8:32 pm

MDW

YVR

10h 02m

1 stop

$411Delta

Sat, Oct 10 - Tue, Oct 13

7:35 pm - 8:49 am

YVR

MDW

11h 14m

2 stops

1:00 pm - 10:35 pm

MDW

YVR

11h 35m

2 stops

$412Delta

Tue, Oct 6 - Tue, Oct 13

6:00 am - 5:56 pm

YVR

MDW

9h 56m

2 stops

9:54 am - 7:10 pm

MDW

YVR

11h 16m

2 stops

$413Delta

Tue, Jun 2 - Tue, Jun 9

Delta flights from Vancouver to Chicago Midway Airport

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

Delta

May 27

YVR6:00 amVancouver Intl

10h 33m

2 stops

MDW6:33 pmChicago Midway

Jun 1

MDW1:59 pmChicago Midway

8h 40m

1 stop

YVR8:39 pmVancouver Intl

$376

Delta

Oct 10

YVR6:15 amVancouver Intl

8h 35m

1 stop

MDW4:50 pmChicago Midway

Oct 13

MDW12:30 pmChicago Midway

10h 02m

1 stop

YVR8:32 pmVancouver Intl

$381

Delta

May 23

YVR6:00 amVancouver Intl

9h 56m

1 stop

MDW5:56 pmChicago Midway

May 31

MDW9:23 amChicago Midway

11h 47m

2 stops

YVR7:10 pmVancouver Intl

$401

WestJet flights from Vancouver to Chicago Midway Airport

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

WestJet

Apr 27

YVR5:00 amVancouver Intl

11h 36m

2 stops

MDW6:36 pmChicago Midway

May 17

MDW9:23 amChicago Midway

11h 47m

2 stops

YVR7:10 pmVancouver Intl

$785

WestJet

Apr 27

YVR6:00 amVancouver Intl

10h 36m

2 stops

MDW6:36 pmChicago Midway

May 17

MDW9:22 amChicago Midway

16h 53m

2 stops

YVR12:15 amVancouver Intl

$786

WestJet

Apr 27

YVR10:55 pmVancouver Intl

15h 31m

1 stop

MDW4:26 pmChicago Midway

May 17

MDW9:23 amChicago Midway

14h 17m

2 stops

YVR9:40 pmVancouver Intl

$788

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

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 5/23

9:30 am-10:02 pm

1 stop10h 32m

Chicago Midway

Tue 6/2

6:00 am-7:10 pm

2 stops15h 10m

$374

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 5/27

6:00 am-6:33 pm

2 stops10h 33m

Chicago Midway

Mon 6/1

1:59 pm-8:39 pm

1 stop8h 40m

$376

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 5/26

10:55 pm-11:09 am

1 stop10h 14m

Chicago Midway

Tue 6/2

6:00 am-7:10 pm

2 stops15h 10m

$378

Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

6:15 am-4:50 pm

1 stop8h 35m

Chicago Midway

Tue 10/13

12:30 pm-8:32 pm

1 stop10h 02m

$381

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 5/23

6:20 am-5:56 pm

2 stops9h 36m

Chicago Midway

Fri 5/29

1:22 pm-10:35 pm

2 stops11h 13m

$401

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/21

6:00 am-5:56 pm

1 stop9h 56m

Chicago Midway

Wed 6/3

9:23 am-7:10 pm

2 stops11h 47m

$407

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

5:15 pm-8:49 am

2 stops13h 34m

Chicago Midway

Tue 10/13

9:30 am-8:32 pm

2 stops13h 02m

$409

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

7:35 pm-8:49 am

2 stops11h 14m

Chicago Midway

Tue 10/13

12:30 pm-8:32 pm

1 stop10h 02m

$411

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/6

7:35 pm-8:49 am

2 stops11h 14m

Chicago Midway

Tue 10/13

1:00 pm-10:35 pm

2 stops11h 35m

$412

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 6/2

6:00 am-5:56 pm

2 stops9h 56m

Chicago Midway

Tue 6/9

9:54 am-7:10 pm

2 stops11h 16m

$413

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

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. 9h 50m 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.

Frequently asked questions about flying from Vancouver to Chicago Midway Airport

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

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

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.