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Cheap flights from Vancouver Intl Airport to Chicago from C$ 290

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 11/8. 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
6:00 a.m. - 6:18 p.m.
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:49 p.m. - 8:31 p.m.
MDW
-
YVR
8h 42m
1 stop
C$ 599Delta
Sun, 7 Jun - Mon, 29 Jun
Delta Logo
6:00 a.m. - 6:18 p.m.
YVR
-
MDW
10h 18m
1 stop
Delta Logo
6:58 p.m. - 1:30 p.m.
MDW
-
YVR
20h 32m
2 stops
C$ 600Delta
Sun, 7 Jun - Wed, 1 Jul
Delta Logo
6:00 a.m. - 6:18 p.m.
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:49 p.m. - 8:31 p.m.
MDW
-
YVR
8h 42m
1 stop
C$ 615Delta
Tue, 23 Jun - Mon, 29 Jun
Delta Logo
6:00 a.m. - 6:33 p.m.
YVR
-
MDW
10h 33m
2 stops
Delta Logo
1:49 p.m. - 10:35 p.m.
MDW
-
YVR
10h 46m
2 stops
C$ 618Delta
Sat, 6 Jun - Sat, 13 Jun
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$ 630Delta
Mon, 19 Oct - Wed, 21 Oct
Delta Logo
6:00 a.m. - 6:18 p.m.
YVR
-
MDW
10h 18m
1 stop
Delta Logo
5:47 p.m. - 2:53 p.m.
MDW
-
YVR
23h 06m
2 stops
C$ 633Delta
Sun, 7 Jun - Sat, 27 Jun
Delta Logo
6:00 a.m. - 6:18 p.m.
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:49 p.m. - 8:31 p.m.
MDW
-
YVR
8h 42m
1 stop
C$ 634Delta
Tue, 23 Jun - Mon, 29 Jun
Delta Logo
6:00 a.m. - 6:18 p.m.
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:49 p.m. - 8:31 p.m.
MDW
-
YVR
8h 42m
1 stop
C$ 636Delta
Sun, 7 Jun - Wed, 1 Jul
Multiple Airlines Logo
10:55 p.m. - 11:07 a.m.
YVR
-
MDW
10h 12m
1 stop
Multiple Airlines Logo
12:11 p.m. - 12:15 a.m.
MDW
-
YVR
14h 04m
2 stops
C$ 644Multiple Airlines
Thu, 13 Aug - Mon, 17 Aug
Delta Logo
6:15 a.m. - 6:25 p.m.
YVR
-
MDW
10h 10m
2 stops
Delta Logo
1:49 p.m. - 10:28 p.m.
MDW
-
YVR
10h 39m
2 stops
C$ 652Delta
Thu, 9 Jul - Mon, 13 Jul

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
7 Jun
YVR6:00 a.m.Vancouver Intl
10h 18m
1 stop
MDW6:18 p.m.Chicago Midway
29 Jun
MDW1:49 p.m.Chicago Midway
8h 42m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 599
Delta
7 Jun
YVR6:00 a.m.Vancouver Intl
10h 18m
1 stop
MDW6:18 p.m.Chicago Midway
1 Jul
MDW6:58 p.m.Chicago Midway
20h 32m
2 stops
YVR1:30 p.m.Vancouver Intl
C$ 600
Delta
23 Jun
YVR6:00 a.m.Vancouver Intl
10h 18m
1 stop
MDW6:18 p.m.Chicago Midway
29 Jun
MDW1:26 p.m.Chicago Midway
9h 05m
2 stops
YVR8:31 p.m.Vancouver Intl
C$ 615

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
25 May
YVR6:05 a.m.Vancouver Intl
9h 56m
1 stop
MDW6:01 p.m.Chicago Midway
26 May
MDW2:04 p.m.Chicago Midway
8h 40m
1 stop
YVR8:44 p.m.Vancouver Intl
C$ 998
WestJet
20 May
YVR6:45 a.m.Vancouver Intl
9h 48m
2 stops
MDW6:33 p.m.Chicago Midway
24 May
MDW1:22 p.m.Chicago Midway
23h 33m
1 stop
YVR10:55 a.m.Vancouver Intl
C$ 1,149
WestJet
21 May
YVR6:00 a.m.Vancouver Intl
10h 33m
2 stops
MDW6:33 p.m.Chicago Midway
26 May
MDW9:23 a.m.Chicago Midway
13h 16m
1 stop
YVR8:39 p.m.Vancouver Intl
C$ 1,151

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 12 May 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
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 7/6

6:00 a.m.-6:18 p.m.

1 stop10h 18m

Chicago Midway

Mon 29/6

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 599

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 7/6

6:00 a.m.-6:18 p.m.

1 stop10h 18m

Chicago Midway

Wed 1/7

6:58 p.m.-1:30 p.m.

2 stops20h 32m

C$ 600

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 23/6

6:00 a.m.-6:18 p.m.

1 stop10h 18m

Chicago Midway

Mon 29/6

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 615

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 6/6

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

2 stops10h 33m

Chicago Midway

Sat 13/6

1:49 p.m.-10:35 p.m.

2 stops10h 46m

C$ 618

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 19/10

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

2 stops13h 34m

Chicago Midway

Wed 21/10

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

1 stop10h 02m

C$ 630

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 7/6

6:00 a.m.-6:18 p.m.

1 stop10h 18m

Chicago Midway

Sat 27/6

5:47 p.m.-2:53 p.m.

2 stops23h 06m

C$ 633

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 23/6

6:00 a.m.-6:18 p.m.

1 stop10h 18m

Chicago Midway

Mon 29/6

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 634

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 7/6

6:00 a.m.-6:18 p.m.

1 stop10h 18m

Chicago Midway

Wed 1/7

1:49 p.m.-8:31 p.m.

1 stop8h 42m

C$ 636

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 13/8

10:55 p.m.-11:07 a.m.

1 stop10h 12m

Chicago Midway

Mon 17/8

12:11 p.m.-12:15 a.m.

2 stops14h 04m

C$ 644

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 9/7

6:15 a.m.-6:25 p.m.

2 stops10h 10m

Chicago Midway

Mon 13/7

1:49 p.m.-10:28 p.m.

2 stops10h 39m

C$ 652

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 05m

Direct flights

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

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 9h 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?

    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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