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Cheap flights from Vancouver to Chicago from C$ 311

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 to Chicago departing on 30/8. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Vancouver to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:00 a.m. - 6:11 p.m.
YVR
-
MDW
10h 11m
1 stop
Delta Logo
1:47 p.m. - 11:08 p.m.
MDW
-
YVR
11h 21m
2 stops
C$ 570Delta
Thu, 24 Sep - Wed, 30 Sep
Delta Logo
6:00 a.m. - 6:11 p.m.
YVR
-
MDW
10h 11m
1 stop
Delta Logo
1:47 p.m. - 8:26 p.m.
MDW
-
YVR
8h 39m
1 stop
C$ 572Delta
Thu, 24 Sep - Wed, 30 Sep
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$ 575WestJet
Fri, 11 Sep - Mon, 14 Sep
Delta Logo
5:15 p.m. - 8:49 a.m.
YVR
-
MDW
13h 34m
2 stops
Delta Logo
12:30 p.m. - 7:10 p.m.
MDW
-
YVR
8h 40m
2 stops
C$ 607Delta
Sat, 10 Oct - Tue, 13 Oct
Delta Logo
5:30 p.m. - 12:34 p.m.
YVR
-
MDW
17h 04m
2 stops
Delta Logo
1:47 p.m. - 12:15 a.m.
MDW
-
YVR
12h 28m
2 stops
C$ 630Delta
Sat, 19 Sep - Wed, 30 Sep
Delta Logo
10:55 p.m. - 9:52 a.m.
YVR
-
MDW
8h 57m
1 stop
Delta Logo
12:30 p.m. - 7:10 p.m.
MDW
-
YVR
8h 40m
2 stops
C$ 648Delta
Sat, 10 Oct - Tue, 13 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$ 650Delta
Sat, 10 Oct - Sun, 18 Oct
Delta Logo
6:00 a.m. - 6:11 p.m.
YVR
-
MDW
10h 11m
1 stop
Delta Logo
1:47 p.m. - 8:26 p.m.
MDW
-
YVR
8h 39m
1 stop
C$ 657Delta
Thu, 24 Sep - Wed, 30 Sep
Delta Logo
6:00 a.m. - 6:18 p.m.
YVR
-
MDW
10h 18m
1 stop
Delta Logo
1:49 p.m. - 8:29 p.m.
MDW
-
YVR
8h 40m
1 stop
C$ 678Delta
Mon, 13 Jul - Mon, 20 Jul
WestJet Logo
6:05 a.m. - 6:06 p.m.
YVR
-
MDW
10h 01m
1 stop
WestJet Logo
1:56 p.m. - 8:37 p.m.
MDW
-
YVR
8h 41m
1 stop
C$ 686WestJet
Fri, 7 Aug - Sat, 15 Aug

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WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver 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$ 574
WestJet
7 Aug
YVR6:05 a.m.Vancouver Intl
10h 01m
1 stop
MDW6:06 p.m.Chicago Midway
15 Aug
MDW1:56 p.m.Chicago Midway
8h 41m
1 stop
YVR8:37 p.m.Vancouver Intl
C$ 686
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$ 696

Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets
Delta
24 Sep
YVR6:00 a.m.Vancouver Intl
10h 11m
1 stop
MDW6:11 p.m.Chicago Midway
30 Sep
MDW1:47 p.m.Chicago Midway
11h 21m
2 stops
YVR11:08 p.m.Vancouver Intl
C$ 570
Delta
24 Sep
YVR6:00 a.m.Vancouver Intl
10h 11m
1 stop
MDW6:11 p.m.Chicago Midway
30 Sep
MDW1:47 p.m.Chicago Midway
8h 39m
1 stop
YVR8:26 p.m.Vancouver Intl
C$ 572
Delta
10 Oct
YVR5:15 p.m.Vancouver Intl
13h 34m
2 stops
MDW8:49 a.m.Chicago Midway
13 Oct
MDW12:30 p.m.Chicago Midway
8h 40m
2 stops
YVR7:10 p.m.Vancouver Intl
C$ 607

momondo Fare Finder

 
Customize your flight search to find flights from Vancouver 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 20 June 2026.
Use the filters below to find and compare flights from Vancouver 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 24/9

6:00 a.m.-6:11 p.m.

1 stop10h 11m

Chicago Midway

Wed 30/9

1:47 p.m.-11:08 p.m.

2 stops11h 21m

C$ 570

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/9

6:00 a.m.-6:11 p.m.

1 stop10h 11m

Chicago Midway

Wed 30/9

1:47 p.m.-8:26 p.m.

1 stop8h 39m

C$ 572

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$ 574

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

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

2 stops13h 34m

Chicago Midway

Tue 13/10

12:30 p.m.-7:10 p.m.

2 stops8h 40m

C$ 607

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 19/9

5:30 p.m.-12:34 p.m.

2 stops17h 04m

Chicago Midway

Wed 30/9

1:47 p.m.-12:15 a.m.

2 stops12h 28m

C$ 630
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

10:55 p.m.-9:52 a.m.

1 stop8h 57m

Chicago Midway

Tue 13/10

12:30 p.m.-7:10 p.m.

2 stops8h 40m

C$ 648

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

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$ 650

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 24/9

6:00 a.m.-6:11 p.m.

1 stop10h 11m

Chicago Midway

Wed 30/9

1:47 p.m.-8:26 p.m.

1 stop8h 39m

C$ 657

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 13/7

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

1 stop10h 18m

Chicago Midway

Mon 20/7

1:49 p.m.-8:29 p.m.

1 stop8h 40m

C$ 678

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 7/8

6:05 a.m.-6:06 p.m.

1 stop10h 01m

Chicago Midway

Sat 15/8

1:56 p.m.-8:37 p.m.

1 stop8h 41m

C$ 686

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 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 to Chicago Midway?

Delta is the most popular carrier operating from Vancouver to Chicago Midway

Cheap Vancouver to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Vancouver to Chicago Midway Airport

Fastest flight time

8h 57m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 8h 57m
There are no direct flights from Vancouver to Chicago Midway Airport. There are no popular flight routes from Vancouver to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Vancouver to Chicago Midway Airport

  • How far is Vancouver to Chicago Midway by plane?

    Vancouver and Chicago Midway are 2846.6 km apart from one another. Flights usually cover this in 8h 57m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Vancouver to Chicago Midway Airport?

    Prices for flights from Vancouver to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Vancouver to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Vancouver to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Vancouver to Chicago. momondo saves you time and could save you money on your trip.

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?

momondo provides multiple filters to help you find the best flight to Chicago from Vancouver. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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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