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Cheap flights from Vancouver Intl Airport to Chicago from $162

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 4/24. 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.
Multiple Airlines Logo
9:30 am - 10:19 pm
YVR
-
MDW
10h 49m
1 stop
Multiple Airlines Logo
6:15 am - 5:30 pm
MDW
-
YVR
13h 15m
2 stops
$334Multiple Airlines
Sat, May 2 - Thu, May 7
Multiple Airlines Logo
11:00 pm - 8:07 pm
YVR
-
MDW
19h 07m
1 stop
Multiple Airlines Logo
2:56 pm - 11:12 am
MDW
-
YVR
22h 16m
1 stop
$343Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
11:00 pm - 8:07 pm
YVR
-
MDW
19h 07m
1 stop
Multiple Airlines Logo
2:56 pm - 11:12 am
MDW
-
YVR
22h 16m
1 stop
$345Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
4:50 pm - 10:05 am
YVR
-
MDW
15h 15m
1 stop
Multiple Airlines Logo
2:20 pm - 10:45 am
MDW
-
YVR
22h 25m
1 stop
$365Multiple Airlines
Sun, Apr 26 - Wed, Apr 29
Multiple Airlines Logo
4:50 pm - 10:05 am
YVR
-
MDW
15h 15m
1 stop
Multiple Airlines Logo
6:00 am - 7:25 pm
MDW
-
YVR
15h 25m
2 stops
$370Multiple Airlines
Sun, Apr 26 - Wed, Apr 29
Multiple Airlines Logo
9:10 am - 10:45 pm
YVR
-
MDW
11h 35m
1 stop
Multiple Airlines Logo
10:36 pm - 4:07 pm
MDW
-
YVR
43h 31m
2 stops
$378Multiple Airlines
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
12:50 pm - 10:05 am
YVR
-
MDW
19h 15m
1 stop
Multiple Airlines Logo
12:45 pm - 9:20 pm
MDW
-
YVR
10h 35m
2 stops
$389Multiple Airlines
Wed, Apr 22 - Sat, Apr 25
Multiple Airlines Logo
12:55 pm - 10:05 am
YVR
-
MDW
19h 10m
1 stop
Multiple Airlines Logo
11:00 am - 8:43 pm
MDW
-
YVR
11h 43m
2 stops
$393Multiple Airlines
Thu, Mar 5 - Thu, Mar 12
Multiple Airlines Logo
9:10 am - 10:45 pm
YVR
-
MDW
11h 35m
1 stop
Multiple Airlines Logo
11:00 am - 10:20 am
MDW
-
YVR
25h 20m
1 stop
$402Multiple Airlines
Thu, Mar 26 - Mon, Mar 30
Multiple Airlines Logo
12:10 am - 3:20 pm
YVR
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
11:00 am - 10:05 pm
MDW
-
YVR
13h 05m
1 stop
$411Multiple Airlines
Thu, Apr 9 - Thu, Apr 23

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
Mar 5
YVR6:20 amVancouver Intl
9h 17m
2 stops
MDW5:37 pmChicago Midway
Mar 10
MDW1:10 pmChicago Midway
12h 49m
2 stops
YVR11:59 pmVancouver Intl
$449
Delta
Apr 22
YVR7:30 pmVancouver Intl
11h 17m
2 stops
MDW8:47 amChicago Midway
Apr 25
MDW9:27 amChicago Midway
13h 43m
2 stops
YVR9:10 pmVancouver Intl
$460
Delta
Mar 2
YVR7:37 pmVancouver Intl
11h 17m
2 stops
MDW8:54 amChicago Midway
Mar 4
MDW1:29 pmChicago Midway
12h 30m
2 stops
YVR11:59 pmVancouver Intl
$467

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
Apr 25
YVR6:00 amVancouver Intl
25h 56m
2 stops
MDW9:56 amChicago Midway
Apr 28
MDW9:31 amChicago Midway
17h 14m
2 stops
YVR12:45 amVancouver Intl
$562
WestJet
Apr 25
YVR5:00 pmVancouver Intl
13h 47m
2 stops
MDW8:47 amChicago Midway
Apr 28
MDW9:27 amChicago Midway
13h 23m
2 stops
YVR8:50 pmVancouver Intl
$565
WestJet
Apr 25
YVR5:00 pmVancouver Intl
13h 47m
2 stops
MDW8:47 amChicago Midway
Apr 28
MDW9:27 amChicago Midway
13h 23m
2 stops
YVR8:50 pmVancouver Intl
$569

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 February 5, 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

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 5/2

9:30 am-10:19 pm

1 stop10h 49m

Chicago Midway

Thu 5/7

6:15 am-5:30 pm

2 stops13h 15m

$334

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/8

11:00 pm-8:07 pm

1 stop19h 07m

Chicago Midway

Sun 4/12

2:56 pm-11:12 am

1 stop22h 16m

$343

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/8

11:00 pm-8:07 pm

1 stop19h 07m

Chicago Midway

Sun 4/12

2:56 pm-11:12 am

1 stop22h 16m

$345

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/26

4:50 pm-10:05 am

1 stop15h 15m

Chicago Midway

Wed 4/29

2:20 pm-10:45 am

1 stop22h 25m

$365

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 4/26

4:50 pm-10:05 am

1 stop15h 15m

Chicago Midway

Wed 4/29

6:00 am-7:25 pm

2 stops15h 25m

$370

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/26

9:10 am-10:45 pm

1 stop11h 35m

Chicago Midway

Mon 3/30

10:36 pm-4:07 pm

2 stops43h 31m

$378

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 4/22

12:50 pm-10:05 am

1 stop19h 15m

Chicago Midway

Sat 4/25

12:45 pm-9:20 pm

2 stops10h 35m

$389

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/5

12:55 pm-10:05 am

1 stop19h 10m

Chicago Midway

Thu 3/12

11:00 am-8:43 pm

2 stops11h 43m

$393

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 3/26

9:10 am-10:45 pm

1 stop11h 35m

Chicago Midway

Mon 3/30

11:00 am-10:20 am

1 stop25h 20m

$402

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 4/9

12:10 am-3:20 pm

1 stop13h 10m

Chicago Midway

Thu 4/23

11:00 am-10:05 pm

1 stop13h 05m

$411

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

8h 40m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 8h 40m
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.

  • How do I get Price Alerts for flights from Vancouver Intl Airport to Chicago Midway Airport?

    Confirm your travel details to search for the latest offers for flights from Vancouver Intl Airport 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 Intl Airport to Chicago Midway Airport with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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
Portage
Lansing
Schererville
Valparaiso
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. 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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