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Cheap flights from Vancouver Intl Airport to Chicago from C$ 310

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 28/9. 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.
WestJet Logo
6:05 a.m. - 6:24 p.m.
YVR
-
MDW
10h 19m
1 stop
WestJet Logo
2:05 p.m. - 8:31 p.m.
MDW
-
YVR
8h 26m
1 stop
C$ 578WestJet
Fri, 11 Sep - Mon, 14 Sep
Delta Logo
6:00 a.m. - 6:19 p.m.
YVR
-
MDW
10h 19m
1 stop
Delta Logo
2:00 p.m. - 8:26 p.m.
MDW
-
YVR
8h 26m
1 stop
C$ 585Delta
Fri, 18 Sep - Wed, 23 Sep
Delta Logo
6:00 a.m. - 6:19 p.m.
YVR
-
MDW
10h 19m
1 stop
Delta Logo
2:00 p.m. - 8:26 p.m.
MDW
-
YVR
8h 26m
1 stop
C$ 586Delta
Fri, 11 Sep - Mon, 14 Sep
Delta Logo
6:00 a.m. - 6:19 p.m.
YVR
-
MDW
10h 19m
1 stop
Delta Logo
2:00 p.m. - 8:26 p.m.
MDW
-
YVR
8h 26m
1 stop
C$ 596Delta
Fri, 18 Sep - Wed, 23 Sep
Delta Logo
5:15 p.m. - 8:49 a.m.
YVR
-
MDW
13h 34m
2 stops
Delta Logo
12:30 p.m. - 8:32 p.m.
MDW
-
YVR
10h 02m
1 stop
C$ 607Delta
Sat, 10 Oct - Sun, 18 Oct
Delta Logo
6:15 a.m. - 4:50 p.m.
YVR
-
MDW
8h 35m
1 stop
Delta Logo
12:30 p.m. - 8:32 p.m.
MDW
-
YVR
10h 02m
1 stop
C$ 610Delta
Sun, 11 Oct - Sun, 18 Oct
Delta Logo
5:45 p.m. - 8:48 a.m.
YVR
-
MDW
13h 03m
2 stops
Delta Logo
2:00 p.m. - 8:26 p.m.
MDW
-
YVR
8h 26m
1 stop
C$ 620Delta
Fri, 11 Sep - Mon, 14 Sep
Multiple Airlines Logo
10:55 p.m. - 10:58 a.m.
YVR
-
MDW
10h 03m
1 stop
Multiple Airlines Logo
7:25 a.m. - 7:10 p.m.
MDW
-
YVR
13h 45m
2 stops
C$ 626Multiple Airlines
Tue, 22 Sep - Tue, 29 Sep
Delta Logo
5:45 p.m. - 8:48 a.m.
YVR
-
MDW
13h 03m
2 stops
Delta Logo
9:24 a.m. - 6:40 p.m.
MDW
-
YVR
11h 16m
2 stops
C$ 654Delta
Fri, 11 Sep - Mon, 14 Sep
Multiple Airlines Logo
10:55 p.m. - 10:58 a.m.
YVR
-
MDW
10h 03m
1 stop
Multiple Airlines Logo
7:25 a.m. - 7:10 p.m.
MDW
-
YVR
13h 45m
2 stops
C$ 670Multiple Airlines
Mon, 28 Sep - Mon, 5 Oct

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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
11 Sep
YVR6:00 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:19 p.m.Chicago Midway
14 Sep
MDW2:00 p.m.Chicago Midway
8h 26m
1 stop
YVR8:26 p.m.Vancouver Intl
C$ 586
Delta
18 Sep
YVR6:00 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:19 p.m.Chicago Midway
23 Sep
MDW2:00 p.m.Chicago Midway
8h 26m
1 stop
YVR8:26 p.m.Vancouver Intl
C$ 596
Delta
10 Oct
YVR6:15 a.m.Vancouver Intl
8h 35m
1 stop
MDW4:50 p.m.Chicago Midway
18 Oct
MDW12:30 p.m.Chicago Midway
10h 02m
1 stop
YVR8:32 p.m.Vancouver Intl
C$ 607

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
11 Sep
YVR6:05 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:24 p.m.Chicago Midway
14 Sep
MDW2:05 p.m.Chicago Midway
8h 26m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 578
WestJet
28 Sep
YVR6:05 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:24 p.m.Chicago Midway
5 Oct
MDW2:05 p.m.Chicago Midway
8h 26m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 700
WestJet
27 Sep
YVR6:05 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:24 p.m.Chicago Midway
30 Sep
MDW2:05 p.m.Chicago Midway
8h 26m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 747

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 25 June 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

Fri 11/9

6:05 a.m.-6:24 p.m.

1 stop10h 19m

Chicago Midway

Mon 14/9

2:05 p.m.-8:31 p.m.

1 stop8h 26m

C$ 578

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 18/9

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

1 stop10h 19m

Chicago Midway

Wed 23/9

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

1 stop8h 26m

C$ 585

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 11/9

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

1 stop10h 19m

Chicago Midway

Mon 14/9

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

1 stop8h 26m

C$ 586

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 18/9

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

1 stop10h 19m

Chicago Midway

Wed 23/9

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

1 stop8h 26m

C$ 596

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

5:15 p.m.-8:49 a.m.

2 stops13h 34m

Chicago Midway

Sun 18/10

12:30 p.m.-8:32 p.m.

1 stop10h 02m

C$ 607
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 11/10

6:15 a.m.-4:50 p.m.

1 stop8h 35m

Chicago Midway

Sun 18/10

12:30 p.m.-8:32 p.m.

1 stop10h 02m

C$ 610

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 11/9

5:45 p.m.-8:48 a.m.

2 stops13h 03m

Chicago Midway

Mon 14/9

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

1 stop8h 26m

C$ 620

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 22/9

10:55 p.m.-10:58 a.m.

1 stop10h 03m

Chicago Midway

Tue 29/9

7:25 a.m.-7:10 p.m.

2 stops13h 45m

C$ 626

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 11/9

5:45 p.m.-8:48 a.m.

2 stops13h 03m

Chicago Midway

Mon 14/9

9:24 a.m.-6:40 p.m.

2 stops11h 16m

C$ 654

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 28/9

10:55 p.m.-10:58 a.m.

1 stop10h 03m

Chicago Midway

Mon 5/10

7:25 a.m.-7:10 p.m.

2 stops13h 45m

C$ 670

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

8h 57m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 8h 57m
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?

    There are 2850.9 km between Vancouver Intl and Chicago Midway. In terms of flight time, this usually takes a little over 8h 57m.

  • 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

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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