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Cheap flights from Vancouver Intl Airport to Chicago from C$ 153

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 18/11. 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
11:00 p.m. - 2:40 p.m.YVR-MDW
13h 40m1 stop
Multiple Airlines Logo
6:05 a.m. - 10:45 p.m.MDW-YVR
18h 40m2 stops
C$ 408Multiple Airlines
Find Deal
Fri, 21 Nov - Tue, 25 Nov
Multiple Airlines Logo
11:00 p.m. - 2:40 p.m.YVR-MDW
13h 40m1 stop
Multiple Airlines Logo
6:05 a.m. - 10:45 p.m.MDW-YVR
18h 40m2 stops
C$ 440Multiple Airlines
Find Deal
Fri, 21 Nov - Tue, 25 Nov
Multiple Airlines Logo
11:00 p.m. - 10:43 p.m.YVR-MDW
21h 43m1 stop
Multiple Airlines Logo
6:05 a.m. - 11:12 a.m.MDW-YVR
31h 07m1 stop
C$ 447Multiple Airlines
Find Deal
Sun, 23 Nov - Fri, 28 Nov
Multiple Airlines Logo
10:30 p.m. - 3:20 p.m.YVR-MDW
14h 50m1 stop
Multiple Airlines Logo
6:05 a.m. - 10:45 p.m.MDW-YVR
18h 40m2 stops
C$ 497Multiple Airlines
Find Deal
Sat, 22 Nov - Fri, 28 Nov
Multiple Airlines Logo
11:00 p.m. - 2:40 p.m.YVR-MDW
13h 40m1 stop
Multiple Airlines Logo
6:05 a.m. - 10:45 p.m.MDW-YVR
18h 40m2 stops
C$ 518Multiple Airlines
Find Deal
Fri, 21 Nov - Wed, 26 Nov
Delta Logo
6:45 a.m. - 6:18 p.m.YVR-MDW
9h 33m2 stops
Delta Logo
6:14 p.m. - 11:01 a.m.MDW-YVR
18h 47m2 stops
C$ 553Delta
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Wed, 17 Dec - Tue, 6 Jan
Delta Logo
7:36 p.m. - 12:34 p.m.YVR-MDW
14h 58m2 stops
Delta Logo
9:34 a.m. - 8:54 p.m.MDW-YVR
13h 20m2 stops
C$ 565Delta
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Wed, 17 Dec - Mon, 5 Jan
Porter Airlines Logo
12:20 p.m. - 10:05 a.m.YVR-MDW
19h 45m2 stops
Porter Airlines Logo
11:00 a.m. - 9:23 p.m.MDW-YVR
12h 23m2 stops
C$ 726Porter Airlines
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Sun, 30 Nov - Wed, 3 Dec
WestJet Logo
5:00 p.m. - 1:07 p.m.YVR-MDW
18h 07m2 stops
WestJet Logo
9:41 a.m. - 9:15 p.m.MDW-YVR
13h 34m2 stops
C$ 730WestJet
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Fri, 21 Nov - Fri, 28 Nov
WestJet Logo
5:00 p.m. - 1:07 p.m.YVR-MDW
18h 07m2 stops
WestJet Logo
9:41 a.m. - 10:44 p.m.MDW-YVR
15h 03m3 stops
C$ 755WestJet
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Fri, 21 Nov - Tue, 25 Nov

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
17 Dec
YVR6:45 a.m.Vancouver Intl
9h 33m
2 stops
MDW6:18 p.m.Chicago Midway
6 Jan
MDW6:14 p.m.Chicago Midway
18h 47m
2 stops
YVR11:01 a.m.Vancouver Intl
C$ 553
Find similar
Delta
17 Dec
YVR7:36 p.m.Vancouver Intl
14h 58m
2 stops
MDW12:34 p.m.Chicago Midway
5 Jan
MDW9:34 a.m.Chicago Midway
13h 20m
2 stops
YVR8:54 p.m.Vancouver Intl
C$ 565
Find similar
Delta
23 Dec
YVR7:32 p.m.Vancouver Intl
13h 34m
2 stops
MDW11:06 a.m.Chicago Midway
6 Jan
MDW6:14 p.m.Chicago Midway
18h 47m
2 stops
YVR11:01 a.m.Vancouver Intl
C$ 586
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
21 Nov
YVR5:00 p.m.Vancouver Intl
18h 07m
2 stops
MDW1:07 p.m.Chicago Midway
28 Nov
MDW9:41 a.m.Chicago Midway
13h 34m
2 stops
YVR9:15 p.m.Vancouver Intl
C$ 730
Find similar
WestJet
21 Nov
YVR5:00 p.m.Vancouver Intl
18h 07m
2 stops
MDW1:07 p.m.Chicago Midway
25 Nov
MDW9:41 a.m.Chicago Midway
15h 03m
3 stops
YVR10:44 p.m.Vancouver Intl
C$ 755
Find similar
WestJet
22 Nov
YVR2:15 p.m.Vancouver Intl
20h 52m
2 stops
MDW1:07 p.m.Chicago Midway
29 Nov
MDW1:47 p.m.Chicago Midway
21h 17m
2 stops
YVR9:04 a.m.Vancouver Intl
C$ 762
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 96,600 searches. Data last updated 3 November 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

Fri 21/11

11:00 p.m.-2:40 p.m.

1 stop13h 40m

Chicago Midway

Tue 25/11

6:05 a.m.-10:45 p.m.

2 stops18h 40m

C$ 408

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 21/11

11:00 p.m.-2:40 p.m.

1 stop13h 40m

Chicago Midway

Tue 25/11

6:05 a.m.-10:45 p.m.

2 stops18h 40m

C$ 440

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 23/11

11:00 p.m.-10:43 p.m.

1 stop21h 43m

Chicago Midway

Fri 28/11

6:05 a.m.-11:12 a.m.

1 stop31h 07m

C$ 447

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 22/11

10:30 p.m.-3:20 p.m.

1 stop14h 50m

Chicago Midway

Fri 28/11

6:05 a.m.-10:45 p.m.

2 stops18h 40m

C$ 497

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 21/11

11:00 p.m.-2:40 p.m.

1 stop13h 40m

Chicago Midway

Wed 26/11

6:05 a.m.-10:45 p.m.

2 stops18h 40m

C$ 518

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 17/12

6:45 a.m.-6:18 p.m.

2 stops9h 33m

Chicago Midway

Tue 6/1

6:14 p.m.-11:01 a.m.

2 stops18h 47m

C$ 553

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 17/12

7:36 p.m.-12:34 p.m.

2 stops14h 58m

Chicago Midway

Mon 5/1

9:34 a.m.-8:54 p.m.

2 stops13h 20m

C$ 565

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 30/11

12:20 p.m.-10:05 a.m.

2 stops19h 45m

Chicago Midway

Wed 3/12

11:00 a.m.-9:23 p.m.

2 stops12h 23m

C$ 726

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 21/11

5:00 p.m.-1:07 p.m.

2 stops18h 07m

Chicago Midway

Fri 28/11

9:41 a.m.-9:15 p.m.

2 stops13h 34m

C$ 730

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 21/11

5:00 p.m.-1:07 p.m.

2 stops18h 07m

Chicago Midway

Tue 25/11

9:41 a.m.-10:44 p.m.

3 stops15h 03m

C$ 755

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

    There are 2850.9 km between Vancouver Intl and Chicago Midway. In terms of flight time, this usually takes a little over 8h 51m.

  • 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?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

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?

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?

Yes. momondo can track prices for Vancouver to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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