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Cheap flights from Vancouver to Chicago from C$ 268

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 2/5. 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
1 adult, Economy, 0 bags

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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.
Multiple Airlines Logo
10:55 p.m. - 6:37 p.m.
YVR
-
MDW
17h 42m
1 stop
Multiple Airlines Logo
12:27 p.m. - 1:40 p.m.
MDW
-
YVR
27h 13m
2 stops
C$ 490Multiple Airlines
Fri, 1 May - Tue, 5 May
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$ 585Delta
Thu, 16 Apr - Wed, 22 Apr
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
Multiple Airlines Logo
10:55 p.m. - 10:14 p.m.
YVR
-
MDW
21h 19m
1 stop
Multiple Airlines Logo
10:25 a.m. - 10:05 p.m.
MDW
-
YVR
13h 40m
1 stop
C$ 609Multiple Airlines
Fri, 1 May - Tue, 5 May
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
6:15 a.m. - 5:58 p.m.
YVR
-
MDW
9h 43m
2 stops
Delta Logo
2:12 p.m. - 10:31 p.m.
MDW
-
YVR
10h 19m
2 stops
C$ 631Delta
Fri, 17 Apr - Sun, 19 Apr
Multiple Airlines Logo
6:40 p.m. - 11:09 a.m.
YVR
-
MDW
14h 29m
2 stops
Multiple Airlines Logo
10:25 a.m. - 8:50 p.m.
MDW
-
YVR
12h 25m
1 stop
C$ 637Multiple Airlines
Tue, 19 May - Tue, 26 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 flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets
Delta
16 Apr
YVR7:23 a.m.Vancouver Intl
8h 35m
2 stops
MDW5:58 p.m.Chicago Midway
22 Apr
MDW1:24 p.m.Chicago Midway
11h 37m
2 stops
YVR11:01 p.m.Vancouver Intl
C$ 585
Delta
1 May
YVR7:30 p.m.Vancouver Intl
15h 13m
2 stops
MDW12:43 p.m.Chicago Midway
5 May
MDW10:41 a.m.Chicago Midway
13h 50m
2 stops
YVR10:31 p.m.Vancouver Intl
C$ 604
Delta
19 May
YVR7:41 p.m.Vancouver Intl
11h 01m
2 stops
MDW8:42 a.m.Chicago Midway
30 May
MDW1:59 p.m.Chicago Midway
8h 40m
1 stop
YVR8:39 p.m.Vancouver Intl
C$ 616

Porter Airlines flights from Vancouver to Chicago Midway Airport

Our best Porter Airlines deals on Vancouver 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
3 Apr
YVR10:05 p.m.Vancouver Intl
12h 05m
1 stop
MDW12:10 p.m.Chicago Midway
5 Apr
MDW4:05 p.m.Chicago Midway
21h 11m
2 stops
YVR11:16 a.m.Vancouver Intl
C$ 910

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 21 March 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

Fri 1/5

10:55 p.m.-6:37 p.m.

1 stop17h 42m

Chicago Midway

Tue 5/5

12:27 p.m.-1:40 p.m.

2 stops27h 13m

C$ 490

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$ 585

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 1/5

10:55 p.m.-10:14 p.m.

1 stop21h 19m

Chicago Midway

Tue 5/5

10:25 a.m.-10:05 p.m.

1 stop13h 40m

C$ 609

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 17/4

6:15 a.m.-5:58 p.m.

2 stops9h 43m

Chicago Midway

Sun 19/4

2:12 p.m.-10:31 p.m.

2 stops10h 19m

C$ 631

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Tue 19/5

6:40 p.m.-11:09 a.m.

2 stops14h 29m

Chicago Midway

Tue 26/5

10:25 a.m.-8:50 p.m.

1 stop12h 25m

C$ 637

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

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 40m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 8h 40m
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

  • 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 40m, 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
Munster
Hammond

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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