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Cheap flights from Vancouver to Chicago from C$ 286

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 1/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Vancouver to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:15 a.m. - 6:31 p.m.
YVR
-
MDW
10h 16m
2 stops
Delta Logo
1:49 p.m. - 8:31 p.m.
MDW
-
YVR
8h 42m
1 stop
C$ 550Delta
Wed, 17 Jun - Wed, 24 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$ 555Delta
Mon, 22 Jun - Sun, 5 Jul
Delta Logo
6:00 a.m. - 5:56 p.m.
YVR
-
MDW
9h 56m
1 stop
Delta Logo
1:49 p.m. - 8:31 p.m.
MDW
-
YVR
8h 42m
1 stop
C$ 567Delta
Wed, 3 Jun - Tue, 9 Jun
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$ 597Delta
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$ 631Delta
Sat, 10 Oct - Tue, 13 Oct
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$ 633Delta
Sat, 10 Oct - Tue, 13 Oct
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, 9 Jun - Thu, 11 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$ 637Delta
Mon, 22 Jun - Sun, 5 Jul
Delta Logo
6:15 a.m. - 6:31 p.m.
YVR
-
MDW
10h 16m
2 stops
Delta Logo
1:26 p.m. - 8:31 p.m.
MDW
-
YVR
9h 05m
2 stops
C$ 641Delta
Wed, 17 Jun - Wed, 24 Jun
Multiple Airlines Logo
6:40 p.m. - 11:12 a.m.
YVR
-
MDW
14h 32m
2 stops
Multiple Airlines Logo
10:15 a.m. - 12:44 a.m.
MDW
-
YVR
16h 29m
1 stop
C$ 642Multiple Airlines
Mon, 8 Jun - Tue, 16 Jun

Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets
Delta
17 Jun
YVR6:15 a.m.Vancouver Intl
10h 16m
2 stops
MDW6:31 p.m.Chicago Midway
24 Jun
MDW1:49 p.m.Chicago Midway
8h 42m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 550
Delta
22 Jun
YVR6:00 a.m.Vancouver Intl
10h 18m
1 stop
MDW6:18 p.m.Chicago Midway
5 Jul
MDW1:49 p.m.Chicago Midway
8h 42m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 555
Delta
3 Jun
YVR6:00 a.m.Vancouver Intl
9h 56m
1 stop
MDW5:56 p.m.Chicago Midway
9 Jun
MDW1:49 p.m.Chicago Midway
8h 42m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 567

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets
WestJet
13 May
YVR10:55 p.m.Vancouver Intl
9h 05m
1 stop
MDW10:00 a.m.Chicago Midway
17 May
MDW9:23 a.m.Chicago Midway
11h 47m
2 stops
YVR7:10 p.m.Vancouver Intl
C$ 1,090
WestJet
15 May
YVR5:00 a.m.Vancouver Intl
11h 33m
2 stops
MDW6:33 p.m.Chicago Midway
25 May
MDW1:22 p.m.Chicago Midway
12h 53m
2 stops
YVR12:15 a.m.Vancouver Intl
C$ 1,094
WestJet
17 May
YVR6:45 a.m.Vancouver Intl
9h 48m
2 stops
MDW6:33 p.m.Chicago Midway
20 May
MDW9:22 a.m.Chicago Midway
13h 53m
2 stops
YVR9:15 p.m.Vancouver Intl
C$ 1,098

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 5 May 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

Wed 17/6

6:15 a.m.-6:31 p.m.

2 stops10h 16m

Chicago Midway

Wed 24/6

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

1 stop8h 42m

C$ 550

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 22/6

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

1 stop10h 18m

Chicago Midway

Sun 5/7

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

1 stop8h 42m

C$ 555

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 3/6

6:00 a.m.-5:56 p.m.

1 stop9h 56m

Chicago Midway

Tue 9/6

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

1 stop8h 42m

C$ 567
Quickest round-trip

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

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

1 stop8h 35m

Chicago Midway

Tue 13/10

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

1 stop10h 02m

C$ 597

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 10/10

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

1 stop8h 35m

Chicago Midway

Tue 13/10

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

1 stop10h 02m

C$ 631

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.-8:32 p.m.

1 stop10h 02m

C$ 633

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 9/6

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

1 stop10h 18m

Chicago Midway

Thu 11/6

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

1 stop8h 42m

C$ 634

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 22/6

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

1 stop10h 18m

Chicago Midway

Sun 5/7

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

1 stop8h 42m

C$ 637

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 17/6

6:15 a.m.-6:31 p.m.

2 stops10h 16m

Chicago Midway

Wed 24/6

1:26 p.m.-8:31 p.m.

2 stops9h 05m

C$ 641

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Mon 8/6

6:40 p.m.-11:12 a.m.

2 stops14h 32m

Chicago Midway

Tue 16/6

10:15 a.m.-12:44 a.m.

1 stop16h 29m

C$ 642

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

9h 16m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 9h 16m
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 9h 16m, 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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