Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Vancouver Intl Airport to Chicago from $111

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 Intl Airport to Chicago departing on 10/31. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Vancouver Intl Airport to Chicago

Cheap round-trip flights

Multiple Airlines Logo
8:30 pm - 1:38 pmYVR-MDW
15h 08m2 stops
Multiple Airlines Logo
8:05 am - 8:48 pmMDW-YVR
14h 43m1 stop
$202Multiple Airlines
Find Deal
Mon, Oct 20 - Wed, Oct 22
Multiple Airlines Logo
8:30 pm - 1:38 pmYVR-MDW
15h 08m2 stops
Multiple Airlines Logo
8:05 am - 8:48 pmMDW-YVR
14h 43m1 stop
$203Multiple Airlines
Find Deal
Tue, Oct 14 - Wed, Oct 22
Multiple Airlines Logo
8:30 pm - 1:38 pmYVR-MDW
15h 08m2 stops
Multiple Airlines Logo
8:05 am - 8:48 pmMDW-YVR
14h 43m1 stop
$204Multiple Airlines
Find Deal
Tue, Oct 14 - Tue, Oct 21
Multiple Airlines Logo
8:30 pm - 11:41 pmYVR-MDW
25h 11m2 stops
Multiple Airlines Logo
6:20 am - 8:48 pmMDW-YVR
16h 28m1 stop
$210Multiple Airlines
Find Deal
Fri, Oct 3 - Mon, Oct 6
Multiple Airlines Logo
11:00 pm - 11:05 pmYVR-MDW
22h 05m1 stop
Multiple Airlines Logo
8:00 am - 10:45 pmMDW-YVR
16h 45m2 stops
$214Multiple Airlines
Find Deal
Sun, Dec 14 - Tue, Dec 16
Multiple Airlines Logo
11:00 pm - 6:39 pmYVR-MDW
17h 39m1 stop
Multiple Airlines Logo
6:15 am - 11:12 amMDW-YVR
30h 57m1 stop
$229Multiple Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
Multiple Airlines Logo
9:30 am - 11:46 pmYVR-MDW
12h 16m1 stop
Multiple Airlines Logo
9:26 pm - 11:12 amMDW-YVR
15h 46m1 stop
$232Multiple Airlines
Find Deal
Fri, Oct 24 - Sun, Oct 26
Multiple Airlines Logo
8:30 pm - 1:38 pmYVR-MDW
15h 08m2 stops
Multiple Airlines Logo
9:26 pm - 8:48 pmMDW-YVR
25h 22m1 stop
$235Multiple Airlines
Find Deal
Tue, Oct 21 - Thu, Oct 23
Delta Logo
5:55 am - 5:43 pmYVR-MDW
9h 48m1 stop
Delta Logo
1:48 pm - 11:57 pmMDW-YVR
12h 09m2 stops
$246Delta
Find Deal
Sat, Oct 18 - Tue, Oct 28
Delta Logo
5:55 am - 5:35 pmYVR-MDW
9h 40m1 stop
Delta Logo
1:43 pm - 8:31 pmMDW-YVR
8h 48m1 stop
$254Delta
Find Deal
Sat, Sep 27 - Tue, Sep 30

Delta flights from Vancouver Intl Airport to Chicago Midway Airport

Our best Delta deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
Delta
Sep 26
YVR5:55 amVancouver Intl
9h 40m
1 stop
MDW5:35 pmChicago Midway
Sep 30
MDW1:43 pmChicago Midway
8h 48m
1 stop
YVR8:31 pmVancouver Intl
$246
Find similar
Delta
Sep 30
YVR7:44 pmVancouver Intl
11h 09m
2 stops
MDW8:53 amChicago Midway
Oct 11
MDW3:00 pmChicago Midway
7h 35m
1 stop
YVR8:35 pmVancouver Intl
$247
Find similar
Delta
Sep 27
YVR5:55 amVancouver Intl
9h 40m
1 stop
MDW5:35 pmChicago Midway
Sep 30
MDW1:43 pmChicago Midway
8h 48m
1 stop
YVR8:31 pmVancouver Intl
$254
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Vancouver Intl Airport 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 September 17, 2025.
Use the filters below to find and compare flights from Vancouver Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 10/20

8:30 pm-1:38 pm

2 stops15h 08m

Chicago Midway

Wed 10/22

8:05 am-8:48 pm

1 stop14h 43m

$202

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/14

8:30 pm-1:38 pm

2 stops15h 08m

Chicago Midway

Wed 10/22

8:05 am-8:48 pm

1 stop14h 43m

$203

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/14

8:30 pm-1:38 pm

2 stops15h 08m

Chicago Midway

Tue 10/21

8:05 am-8:48 pm

1 stop14h 43m

$204

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 10/3

8:30 pm-11:41 pm

2 stops25h 11m

Chicago Midway

Mon 10/6

6:20 am-8:48 pm

1 stop16h 28m

$210

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 12/14

11:00 pm-11:05 pm

1 stop22h 05m

Chicago Midway

Tue 12/16

8:00 am-10:45 pm

2 stops16h 45m

$214

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 10/31

11:00 pm-6:39 pm

1 stop17h 39m

Chicago Midway

Fri 11/7

6:15 am-11:12 am

1 stop30h 57m

$229

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 10/24

9:30 am-11:46 pm

1 stop12h 16m

Chicago Midway

Sun 10/26

9:26 pm-11:12 am

1 stop15h 46m

$232

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 10/21

8:30 pm-1:38 pm

2 stops15h 08m

Chicago Midway

Thu 10/23

9:26 pm-8:48 pm

1 stop25h 22m

$235

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/18

5:55 am-5:43 pm

1 stop9h 48m

Chicago Midway

Tue 10/28

1:48 pm-11:57 pm

2 stops12h 09m

$246

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 9/27

5:55 am-5:35 pm

1 stop9h 40m

Chicago Midway

Tue 9/30

1:43 pm-8:31 pm

1 stop8h 48m

$254

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Vancouver Intl Airport 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 Intl to Chicago Midway?

Delta and KLM are the most popular carriers operating from Vancouver Intl to Chicago Midway

When to book flights from Vancouver Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Vancouver Intl Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Vancouver Intl Airport to Chicago Midway Airport (YVR to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vancouver Intl Airport to Chicago Midway Airport

Direct flights

None
There are no direct flights from Vancouver Intl Airport to Chicago Midway Airport. There are no popular flight routes from Vancouver Intl Airport to Chicago Midway Airport.
Search flight deals

  • How far is Vancouver Intl to Chicago Midway by plane?

    The distance between Vancouver Intl and Chicago Midway is about 1771.5 mi. A reasonable flight in good conditions will take 8h 40m.

  • When did momondo last update prices for flights from Vancouver Intl Airport to Chicago Midway Airport?

    Prices for flights from Vancouver Intl Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Vancouver Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vancouver Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking 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
Benton Harbor
Saint Joseph
Lansing
Portage
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. All flights to Chicago from Vancouver on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Vancouver to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Vancouver. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Vancouver to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Vancouver to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/17
Fri 10/24
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago