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Cheap flights from Vancouver Intl Airport to Chicago from C$ 278

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 8/5. 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

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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.
Delta Logo
7:23 a.m. - 5:58 p.m.
YVR
-
MDW
8h 35m
2 stops
Delta Logo
1:24 p.m. - 11:01 p.m.
MDW
-
YVR
11h 37m
2 stops
C$ 584Delta
Thu, 16 Apr - Wed, 22 Apr
Delta Logo
7:30 p.m. - 8:47 a.m.
YVR
-
MDW
11h 17m
2 stops
Delta Logo
1:22 p.m. - 10:32 p.m.
MDW
-
YVR
11h 10m
2 stops
C$ 586Delta
Fri, 1 May - Sat, 9 May
Delta Logo
7:30 p.m. - 12:43 p.m.
YVR
-
MDW
15h 13m
2 stops
Delta Logo
10:41 a.m. - 10:31 p.m.
MDW
-
YVR
13h 50m
2 stops
C$ 604Delta
Fri, 1 May - Tue, 5 May
Delta Logo
7:30 p.m. - 9:06 a.m.
YVR
-
MDW
11h 36m
2 stops
Delta Logo
1:24 p.m. - 10:31 p.m.
MDW
-
YVR
11h 07m
2 stops
C$ 606Delta
Fri, 17 Apr - Sat, 25 Apr
Delta Logo
7:41 p.m. - 8:42 a.m.
YVR
-
MDW
11h 01m
2 stops
Delta Logo
1:59 p.m. - 8:39 p.m.
MDW
-
YVR
8h 40m
1 stop
C$ 616Delta
Tue, 19 May - Sat, 30 May
Delta Logo
6:00 a.m. - 6:33 p.m.
YVR
-
MDW
10h 33m
2 stops
Delta Logo
1:59 p.m. - 8:39 p.m.
MDW
-
YVR
8h 40m
1 stop
C$ 627Delta
Fri, 22 May - Sat, 30 May
Delta Logo
7:30 p.m. - 8:47 a.m.
YVR
-
MDW
11h 17m
2 stops
Delta Logo
1:59 p.m. - 8:39 p.m.
MDW
-
YVR
8h 40m
1 stop
C$ 630Delta
Mon, 4 May - Mon, 11 May
Delta Logo
9:27 a.m. - 8:47 a.m.
YVR
-
MDW
21h 20m
2 stops
Delta Logo
1:24 p.m. - 10:27 a.m.
MDW
-
YVR
23h 03m
2 stops
C$ 638Delta
Fri, 1 May - Tue, 5 May
Delta Logo
7:41 p.m. - 8:42 a.m.
YVR
-
MDW
11h 01m
2 stops
Delta Logo
9:22 a.m. - 8:39 p.m.
MDW
-
YVR
13h 17m
2 stops
C$ 643Delta
Tue, 19 May - Thu, 28 May
Delta Logo
5:23 p.m. - 8:42 a.m.
YVR
-
MDW
13h 19m
2 stops
Delta Logo
9:22 a.m. - 8:39 p.m.
MDW
-
YVR
13h 17m
2 stops
C$ 654Delta
Fri, 22 May - Thu, 28 May

Porter Airlines flights from Vancouver Intl Airport to Chicago Midway Airport

Our best Porter Airlines deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
Porter Airlines
9 Apr
YVR10:05 p.m.Vancouver Intl
15h 15m
1 stop
MDW3:20 p.m.Chicago Midway
15 Apr
MDW11:00 a.m.Chicago Midway
11h 40m
2 stops
YVR8:40 p.m.Vancouver Intl
C$ 808
Porter Airlines
16 Apr
YVR10:05 p.m.Vancouver Intl
15h 15m
1 stop
MDW3:20 p.m.Chicago Midway
23 Apr
MDW11:00 a.m.Chicago Midway
11h 40m
2 stops
YVR8:40 p.m.Vancouver Intl
C$ 812
Porter Airlines
17 Apr
YVR8:30 a.m.Vancouver Intl
25h 40m
2 stops
MDW12:10 p.m.Chicago Midway
20 Apr
MDW11:00 a.m.Chicago Midway
11h 40m
2 stops
YVR8:40 p.m.Vancouver Intl
C$ 908

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 May
YVR6:00 a.m.Vancouver Intl
9h 56m
1 stop
MDW5:56 p.m.Chicago Midway
25 May
MDW1:59 p.m.Chicago Midway
8h 40m
1 stop
YVR8:39 p.m.Vancouver Intl
C$ 927
WestJet
18 Apr
YVR10:30 p.m.Vancouver Intl
12h 13m
2 stops
MDW12:43 p.m.Chicago Midway
25 Apr
MDW9:27 a.m.Chicago Midway
13h 41m
2 stops
YVR9:08 p.m.Vancouver Intl
C$ 930
WestJet
3 Apr
YVR4:15 p.m.Vancouver Intl
14h 38m
2 stops
MDW8:53 a.m.Chicago Midway
6 Apr
MDW2:05 p.m.Chicago Midway
10h 35m
2 stops
YVR10:40 p.m.Vancouver Intl
C$ 1,097

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 23 March 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

Thu 16/4

7:23 a.m.-5:58 p.m.

2 stops8h 35m

Chicago Midway

Wed 22/4

1:24 p.m.-11:01 p.m.

2 stops11h 37m

C$ 584

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/5

7:30 p.m.-8:47 a.m.

2 stops11h 17m

Chicago Midway

Sat 9/5

1:22 p.m.-10:32 p.m.

2 stops11h 10m

C$ 586

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/5

7:30 p.m.-12:43 p.m.

2 stops15h 13m

Chicago Midway

Tue 5/5

10:41 a.m.-10:31 p.m.

2 stops13h 50m

C$ 604

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 17/4

7:30 p.m.-9:06 a.m.

2 stops11h 36m

Chicago Midway

Sat 25/4

1:24 p.m.-10:31 p.m.

2 stops11h 07m

C$ 606

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 19/5

7:41 p.m.-8:42 a.m.

2 stops11h 01m

Chicago Midway

Sat 30/5

1:59 p.m.-8:39 p.m.

1 stop8h 40m

C$ 616
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 22/5

6:00 a.m.-6:33 p.m.

2 stops10h 33m

Chicago Midway

Sat 30/5

1:59 p.m.-8:39 p.m.

1 stop8h 40m

C$ 627

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 4/5

7:30 p.m.-8:47 a.m.

2 stops11h 17m

Chicago Midway

Mon 11/5

1:59 p.m.-8:39 p.m.

1 stop8h 40m

C$ 630

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 1/5

9:27 a.m.-8:47 a.m.

2 stops21h 20m

Chicago Midway

Tue 5/5

1:24 p.m.-10:27 a.m.

2 stops23h 03m

C$ 638

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 19/5

7:41 p.m.-8:42 a.m.

2 stops11h 01m

Chicago Midway

Thu 28/5

9:22 a.m.-8:39 p.m.

2 stops13h 17m

C$ 643

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 22/5

5:23 p.m.-8:42 a.m.

2 stops13h 19m

Chicago Midway

Thu 28/5

9:22 a.m.-8:39 p.m.

2 stops13h 17m

C$ 654

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

9h 34m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 9h 34m
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?

    There are 2850.9 km between Vancouver Intl and Chicago Midway. In terms of flight time, this usually takes a little over 9h 34m.

  • 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
Munster
Hammond

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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