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Cheap flights from Vancouver Intl Airport to Chicago from C$ 276

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 11/9. 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
1 adult, Economy, 0 bags

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 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 10:59 p.m.MDW  Chicago Midway-YVR Vancouver Intl
12h 32m2 stops Minneapolis St Paul Seattle/Tacoma Intl
C$ 455Delta
Wed, 23 Sep - Tue, 20 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 8:33 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
C$ 472Delta
Wed, 23 Sep - Fri, 23 Oct
Delta Logo
6:00 a.m. - 4:47 p.m.YVR  Vancouver Intl-MDW Chicago Midway
8h 47m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 8:33 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
C$ 474Delta
Tue, 6 Oct - Sat, 10 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
2:00 p.m. - 10:59 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 59m2 stops Minneapolis St Paul Seattle/Tacoma Intl
C$ 483Delta
Thu, 10 Sep - Tue, 15 Sep
Delta Logo
7:30 p.m. - 8:48 a.m.YVR  Vancouver Intl-MDW Chicago Midway
11h 18m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
12:27 p.m. - 10:36 p.m.MDW  Chicago Midway-YVR Vancouver Intl
12h 09m2 stops Minneapolis St Paul Salt Lake City
C$ 489Delta
Thu, 24 Sep - Mon, 19 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 8:33 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
C$ 490Delta
Sun, 4 Oct - Fri, 9 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
2:00 p.m. - 8:26 p.m.MDW  Chicago Midway-YVR Vancouver Intl
8h 26m1 stop Minneapolis St Paul
C$ 514Delta
Wed, 30 Sep - Sat, 3 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
2:00 p.m. - 8:26 p.m.MDW  Chicago Midway-YVR Vancouver Intl
8h 26m1 stop Minneapolis St Paul
C$ 525Delta
Wed, 30 Sep - Sat, 3 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
2:00 p.m. - 8:26 p.m.MDW  Chicago Midway-YVR Vancouver Intl
8h 26m1 stop Minneapolis St Paul
C$ 527Delta
Wed, 30 Sep - Sat, 3 Oct
Delta Logo
7:00 a.m. - 3:47 p.m.YVR  Vancouver Intl-MDW Chicago Midway
7h 47m1 stop Minneapolis St Paul
Delta Logo
12:30 p.m. - 12:59 a.m.MDW  Chicago Midway-YVR Vancouver Intl
13h 29m2 stops Minneapolis St Paul Seattle/Tacoma Intl
C$ 531Delta
Sun, 8 Nov - Mon, 16 Nov

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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
23 Sep
YVR6:00 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:19 p.m.Chicago Midway
20 Oct
MDW12:27 p.m.Chicago Midway
12h 32m
2 stops
YVR10:59 p.m.Vancouver Intl
C$ 455
Delta
23 Sep
YVR6:00 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:19 p.m.Chicago Midway
23 Oct
MDW12:27 p.m.Chicago Midway
10h 06m
1 stop
YVR8:33 p.m.Vancouver Intl
C$ 472
Delta
6 Oct
YVR6:00 a.m.Vancouver Intl
8h 47m
1 stop
MDW4:47 p.m.Chicago Midway
10 Oct
MDW12:27 p.m.Chicago Midway
10h 06m
1 stop
YVR8:33 p.m.Vancouver Intl
C$ 474

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
17 Aug
YVR7:30 p.m.Vancouver Intl
12h 29m
2 stops
MDW9:59 a.m.Chicago Midway
22 Aug
MDW1:51 p.m.Chicago Midway
8h 41m
1 stop
YVR8:32 p.m.Vancouver Intl
C$ 1,229
WestJet
18 Aug
YVR6:45 a.m.Vancouver Intl
9h 48m
2 stops
MDW6:33 p.m.Chicago Midway
29 Aug
MDW9:24 a.m.Chicago Midway
27h 36m
1 stop
YVR11:00 a.m.Vancouver Intl
C$ 1,238
WestJet
22 Aug
YVR6:00 a.m.Vancouver Intl
10h 01m
2 stops
MDW6:01 p.m.Chicago Midway
24 Aug
MDW6:42 p.m.Chicago Midway
18h 18m
1 stop
YVR11:00 a.m.Vancouver Intl
C$ 1,241

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 11 August 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 Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 23/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 20/10

12:27 p.m.-10:59 p.m.

2 stops12h 32m

C$ 455

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 23/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Fri 23/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 472

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 6/10

6:00 a.m.-4:47 p.m.

1 stop8h 47m

Chicago Midway

Sat 10/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 474

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Thu 10/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 15/9

2:00 p.m.-10:59 p.m.

2 stops10h 59m

C$ 483

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Thu 24/9

7:30 p.m.-8:48 a.m.

2 stops11h 18m

Chicago Midway

Mon 19/10

12:27 p.m.-10:36 p.m.

2 stops12h 09m

C$ 489

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sun 4/10

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Fri 9/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 490
Quickest round-trip

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 30/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Sat 3/10

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 514

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 30/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Sat 3/10

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 525

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 30/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Sat 3/10

2:00 p.m.-8:26 p.m.

1 stop8h 26m

C$ 527

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sun 8/11

7:00 a.m.-3:47 p.m.

1 stop7h 47m

Chicago Midway

Mon 16/11

12:30 p.m.-12:59 a.m.

2 stops13h 29m

C$ 531

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

7h 47m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 7h 47m
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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Frequently asked questions about flying from Vancouver Intl Airport to Chicago Midway Airport

  • 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 7h 47m.

  • 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
Merrillville
Hammond
Munster
Valparaiso
Portage

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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