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Cheap flights from Vancouver Intl Airport to Chicago from $147

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 2/4. 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

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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
10:05 pm - 2:26 pm
YVR
-
MDW
14h 21m2 stops
Multiple Airlines Logo
11:05 am - 10:20 am
MDW
-
YVR
25h 15m1 stop
$291Multiple Airlines
Wed, Feb 18 - Tue, Feb 24
Multiple Airlines Logo
11:00 pm - 11:27 am
YVR
-
MDW
10h 27m1 stop
Multiple Airlines Logo
11:05 am - 10:20 am
MDW
-
YVR
25h 15m1 stop
$300Multiple Airlines
Wed, Feb 18 - Tue, Feb 24
Multiple Airlines Logo
11:00 pm - 11:45 am
YVR
-
MDW
10h 45m1 stop
Multiple Airlines Logo
5:01 pm - 2:45 pm
MDW
-
YVR
23h 44m2 stops
$318Multiple Airlines
Wed, Jan 21 - Mon, Jan 26
Multiple Airlines Logo
12:20 pm - 10:10 am
YVR
-
MDW
19h 50m2 stops
Multiple Airlines Logo
7:30 am - 11:59 pm
MDW
-
YVR
18h 29m1 stop
$327Multiple Airlines
Sun, Feb 1 - Fri, Feb 6
Delta Logo
7:37 pm - 8:52 am
YVR
-
MDW
11h 15m2 stops
Delta Logo
12:46 pm - 11:59 pm
MDW
-
YVR
13h 13m2 stops
$353Delta
Wed, Feb 4 - Wed, Feb 11
Delta Logo
7:37 pm - 8:52 am
YVR
-
MDW
11h 15m2 stops
Delta Logo
9:33 am - 6:44 pm
MDW
-
YVR
11h 11m2 stops
$354Delta
Thu, Jan 29 - Sun, Feb 1
Delta Logo
7:37 pm - 8:52 am
YVR
-
MDW
11h 15m2 stops
Delta Logo
1:49 pm - 11:59 pm
MDW
-
YVR
12h 10m2 stops
$357Delta
Mon, Jan 12 - Wed, Jan 14
Delta Logo
7:37 pm - 8:52 am
YVR
-
MDW
11h 15m2 stops
Delta Logo
9:33 am - 8:54 pm
MDW
-
YVR
13h 21m2 stops
$358Delta
Thu, Jan 22 - Sat, Jan 31
Delta Logo
6:20 am - 8:52 am
YVR
-
MDW
24h 32m2 stops
Delta Logo
1:49 pm - 11:59 pm
MDW
-
YVR
12h 10m2 stops
$361Delta
Mon, Jan 12 - Fri, Jan 16
Multiple Airlines Logo
7:30 am - 11:09 pm
YVR
-
MDW
13h 39m1 stop
Multiple Airlines Logo
11:05 am - 8:43 pm
MDW
-
YVR
11h 38m2 stops
$364Multiple Airlines
Mon, Jan 12 - Thu, Jan 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
Feb 4
YVR7:37 pmVancouver Intl
11h 15m
2 stops
MDW8:52 amChicago Midway
Feb 11
MDW12:46 pmChicago Midway
13h 13m
2 stops
YVR11:59 pmVancouver Intl
$353
Find similar
Delta
Jan 29
YVR7:37 pmVancouver Intl
11h 15m
2 stops
MDW8:52 amChicago Midway
Feb 1
MDW9:33 amChicago Midway
11h 11m
2 stops
YVR6:44 pmVancouver Intl
$354
Find similar
Delta
Jan 12
YVR7:37 pmVancouver Intl
11h 15m
2 stops
MDW8:52 amChicago Midway
Jan 14
MDW1:49 pmChicago Midway
12h 10m
2 stops
YVR11:59 pmVancouver Intl
$357
Find similar

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 15
YVR6:00 amVancouver Intl
10h 31m
2 stops
MDW6:31 pmChicago Midway
Apr 19
MDW9:30 amChicago Midway
13h 38m
2 stops
YVR9:08 pmVancouver Intl
$450
Find similar
WestJet
Mar 27
YVR10:30 pmVancouver Intl
17h 25m
2 stops
MDW5:55 pmChicago Midway
Mar 31
MDW7:20 pmChicago Midway
27h 48m
2 stops
YVR9:08 pmVancouver Intl
$516
Find similar
WestJet
May 14
YVR6:00 amVancouver Intl
10h 31m
2 stops
MDW6:31 pmChicago Midway
May 24
MDW9:20 amChicago Midway
13h 15m
2 stops
YVR8:35 pmVancouver Intl
$669
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 December 21, 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

Wed 2/18

10:05 pm-2:26 pm

2 stops14h 21m

Chicago Midway

Tue 2/24

11:05 am-10:20 am

1 stop25h 15m

$291

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 2/18

11:00 pm-11:27 am

1 stop10h 27m

Chicago Midway

Tue 2/24

11:05 am-10:20 am

1 stop25h 15m

$300

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 1/21

11:00 pm-11:45 am

1 stop10h 45m

Chicago Midway

Mon 1/26

5:01 pm-2:45 pm

2 stops23h 44m

$318

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 2/1

12:20 pm-10:10 am

2 stops19h 50m

Chicago Midway

Fri 2/6

7:30 am-11:59 pm

1 stop18h 29m

$327

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 2/4

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Wed 2/11

12:46 pm-11:59 pm

2 stops13h 13m

$353

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/29

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Sun 2/1

9:33 am-6:44 pm

2 stops11h 11m

$354

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 1/12

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Wed 1/14

1:49 pm-11:59 pm

2 stops12h 10m

$357

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 1/22

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Sat 1/31

9:33 am-8:54 pm

2 stops13h 21m

$358

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 1/12

6:20 am-8:52 am

2 stops24h 32m

Chicago Midway

Fri 1/16

1:49 pm-11:59 pm

2 stops12h 10m

$361

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 1/12

7:30 am-11:09 pm

1 stop13h 39m

Chicago Midway

Thu 1/15

11:05 am-8:43 pm

2 stops11h 38m

$364

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 05m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 8h 05m
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 05m.

  • 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
Valparaiso
Schererville
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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