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Cheap flights from Vancouver Intl Airport to Chicago from $203

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 8/25. 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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Find the cheapest flights from Vancouver Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 am - 6:18 pm
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:49 pm - 8:31 pm
MDW
-
YVR
8h 42m
1 stop
$438Delta
Sun, Jun 7 - Mon, Jun 29
Delta Logo
6:00 am - 6:18 pm
YVR
-
MDW
10h 18m
1 stop
Delta Logo
6:58 pm - 1:30 pm
MDW
-
YVR
20h 32m
2 stops
$439Delta
Sun, Jun 7 - Wed, Jul 1
Delta Logo
6:00 am - 6:18 pm
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:26 pm - 8:31 pm
MDW
-
YVR
9h 05m
2 stops
$450Delta
Tue, Jun 23 - Mon, Jun 29
Delta Logo
6:00 am - 6:33 pm
YVR
-
MDW
10h 33m
2 stops
Delta Logo
1:49 pm - 10:35 pm
MDW
-
YVR
10h 46m
2 stops
$452Delta
Sat, Jun 6 - Sat, Jun 13
Delta Logo
5:15 pm - 8:49 am
YVR
-
MDW
13h 34m
2 stops
Delta Logo
12:30 pm - 8:32 pm
MDW
-
YVR
10h 02m
1 stop
$461Delta
Mon, Oct 19 - Wed, Oct 21
Delta Logo
6:00 am - 6:18 pm
YVR
-
MDW
10h 18m
1 stop
Delta Logo
5:47 pm - 2:53 pm
MDW
-
YVR
23h 06m
2 stops
$463Delta
Sun, Jun 7 - Sat, Jun 27
Delta Logo
6:00 am - 6:18 pm
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:49 pm - 8:31 pm
MDW
-
YVR
8h 42m
1 stop
$465Delta
Sun, Jun 7 - Wed, Jul 1
Multiple Airlines Logo
10:55 pm - 11:07 am
YVR
-
MDW
10h 12m
1 stop
Multiple Airlines Logo
12:11 pm - 12:15 am
MDW
-
YVR
14h 04m
2 stops
$471Multiple Airlines
Thu, Aug 13 - Mon, Aug 17
Delta Logo
6:15 am - 6:25 pm
YVR
-
MDW
10h 10m
2 stops
Delta Logo
1:49 pm - 10:28 pm
MDW
-
YVR
10h 39m
2 stops
$477Delta
Thu, Jul 9 - Mon, Jul 13
Delta Logo
6:00 am - 6:01 pm
YVR
-
MDW
10h 01m
1 stop
Delta Logo
1:52 pm - 8:32 pm
MDW
-
YVR
8h 40m
1 stop
$483Delta
Wed, Aug 12 - Sat, Aug 15

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
Jun 7
YVR6:00 amVancouver Intl
10h 18m
1 stop
MDW6:18 pmChicago Midway
Jun 29
MDW1:49 pmChicago Midway
8h 42m
1 stop
YVR8:31 pmVancouver Intl
$438
Delta
Jun 7
YVR6:00 amVancouver Intl
10h 18m
1 stop
MDW6:18 pmChicago Midway
Jul 1
MDW6:58 pmChicago Midway
20h 32m
2 stops
YVR1:30 pmVancouver Intl
$439
Delta
Jun 23
YVR6:00 amVancouver Intl
10h 18m
1 stop
MDW6:18 pmChicago Midway
Jun 29
MDW1:26 pmChicago Midway
9h 05m
2 stops
YVR8:31 pmVancouver Intl
$450

WestJet flights from Vancouver Intl Airport to Chicago Midway Airport

Our best WestJet deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
WestJet
May 25
YVR6:05 amVancouver Intl
9h 56m
1 stop
MDW6:01 pmChicago Midway
May 26
MDW2:04 pmChicago Midway
8h 40m
1 stop
YVR8:44 pmVancouver Intl
$730
WestJet
May 20
YVR6:45 amVancouver Intl
9h 48m
2 stops
MDW6:33 pmChicago Midway
May 24
MDW1:22 pmChicago Midway
23h 33m
1 stop
YVR10:55 amVancouver Intl
$840
WestJet
May 21
YVR6:00 amVancouver Intl
10h 33m
2 stops
MDW6:33 pmChicago Midway
May 26
MDW9:23 amChicago Midway
13h 16m
1 stop
YVR8:39 pmVancouver Intl
$842

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 May 12, 2026.
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

Cheapest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 6/7

6:00 am-6:18 pm

1 stop10h 18m

Chicago Midway

Mon 6/29

1:49 pm-8:31 pm

1 stop8h 42m

$438

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 6/7

6:00 am-6:18 pm

1 stop10h 18m

Chicago Midway

Wed 7/1

6:58 pm-1:30 pm

2 stops20h 32m

$439

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 6/23

6:00 am-6:18 pm

1 stop10h 18m

Chicago Midway

Mon 6/29

1:26 pm-8:31 pm

2 stops9h 05m

$450

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 6/6

6:00 am-6:33 pm

2 stops10h 33m

Chicago Midway

Sat 6/13

1:49 pm-10:35 pm

2 stops10h 46m

$452

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 10/19

5:15 pm-8:49 am

2 stops13h 34m

Chicago Midway

Wed 10/21

12:30 pm-8:32 pm

1 stop10h 02m

$461

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 6/7

6:00 am-6:18 pm

1 stop10h 18m

Chicago Midway

Sat 6/27

5:47 pm-2:53 pm

2 stops23h 06m

$463

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 6/7

6:00 am-6:18 pm

1 stop10h 18m

Chicago Midway

Wed 7/1

1:49 pm-8:31 pm

1 stop8h 42m

$465

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 8/13

10:55 pm-11:07 am

1 stop10h 12m

Chicago Midway

Mon 8/17

12:11 pm-12:15 am

2 stops14h 04m

$471

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 7/9

6:15 am-6:25 pm

2 stops10h 10m

Chicago Midway

Mon 7/13

1:49 pm-10:28 pm

2 stops10h 39m

$477
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 8/12

6:00 am-6:01 pm

1 stop10h 01m

Chicago Midway

Sat 8/15

1:52 pm-8:32 pm

1 stop8h 40m

$483

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 is the most popular carrier 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

Fastest flight time

9h 56m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 9h 56m
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

Frequently asked questions about flying from Vancouver Intl Airport to Chicago Midway Airport

  • 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 9h 56m.

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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

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