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Cheap flights from Vancouver 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 to Chicago departing on 22/10. 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. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
10:01 a.m. - 10:36 p.m.MDW  Chicago Midway-YVR Vancouver Intl
14h 35m2 stops Minneapolis St Paul Salt Lake City
C$ 479Delta
Tue, 29 Sep - Tue, 27 Oct
Delta Logo
5:45 p.m. - 8:48 a.m.YVR  Vancouver Intl-MDW Chicago Midway
13h 03m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
12:27 p.m. - 10:36 p.m.MDW  Chicago Midway-YVR Vancouver Intl
12h 09m2 stops Minneapolis St Paul Salt Lake City
C$ 479Delta
Tue, 29 Sep - Tue, 27 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 8:33 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
C$ 479Delta
Wed, 30 Sep - Tue, 27 Oct
Delta Logo
5:45 p.m. - 8:48 a.m.YVR  Vancouver Intl-MDW Chicago Midway
13h 03m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
12:27 p.m. - 8:33 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
C$ 479Delta
Wed, 30 Sep - Tue, 27 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 8:33 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
C$ 479Delta
Tue, 29 Sep - Wed, 28 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 10:59 p.m.MDW  Chicago Midway-YVR Vancouver Intl
12h 32m2 stops Minneapolis St Paul Seattle/Tacoma Intl
C$ 479Delta
Tue, 29 Sep - Wed, 28 Oct
Delta Logo
5:45 p.m. - 8:48 a.m.YVR  Vancouver Intl-MDW Chicago Midway
13h 03m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
12:27 p.m. - 10:59 p.m.MDW  Chicago Midway-YVR Vancouver Intl
12h 32m2 stops Minneapolis St Paul Seattle/Tacoma Intl
C$ 479Delta
Wed, 30 Sep - Tue, 27 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 p.m. - 8:33 p.m.MDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
C$ 479Delta
Tue, 29 Sep - Tue, 27 Oct
Delta Logo
5:45 p.m. - 8:48 a.m.YVR  Vancouver Intl-MDW Chicago Midway
13h 03m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
12:27 p.m. - 10:36 p.m.MDW  Chicago Midway-YVR Vancouver Intl
12h 09m2 stops Minneapolis St Paul Salt Lake City
C$ 479Delta
Tue, 29 Sep - Wed, 28 Oct
Delta Logo
6:00 a.m. - 6:19 p.m.YVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
1:19 p.m. - 9:10 p.m.MDW  Chicago Midway-YVR Vancouver Intl
9h 51m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
C$ 481Delta
Tue, 15 Sep - Tue, 22 Sep

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Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver to Chicago Midway Airport flight tickets
Delta
29 Sep
YVR6:00 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:19 p.m.Chicago Midway
27 Oct
MDW12:27 p.m.Chicago Midway
10h 06m
1 stop
YVR8:33 p.m.Vancouver Intl
C$ 479
Delta
15 Sep
YVR6:00 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:19 p.m.Chicago Midway
22 Sep
MDW2:00 p.m.Chicago Midway
8h 26m
1 stop
YVR8:26 p.m.Vancouver Intl
C$ 481
Delta
2 Oct
YVR6:00 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:19 p.m.Chicago Midway
28 Oct
MDW9:29 a.m.Chicago Midway
13h 44m
2 stops
YVR9:13 p.m.Vancouver Intl
C$ 498

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets
WestJet
30 Sep
YVR6:05 a.m.Vancouver Intl
10h 19m
1 stop
MDW6:24 p.m.Chicago Midway
28 Oct
MDW12:32 p.m.Chicago Midway
10h 06m
1 stop
YVR8:38 p.m.Vancouver Intl
C$ 527
WestJet
23 Oct
YVR6:05 a.m.Vancouver Intl
8h 47m
1 stop
MDW4:52 p.m.Chicago Midway
30 Oct
MDW12:32 p.m.Chicago Midway
10h 06m
1 stop
YVR8:38 p.m.Vancouver Intl
C$ 544
WestJet
2 Sep
YVR6:05 a.m.Vancouver Intl
10h 01m
1 stop
MDW6:06 p.m.Chicago Midway
9 Sep
MDW2:05 p.m.Chicago Midway
8h 26m
1 stop
YVR8:31 p.m.Vancouver Intl
C$ 625

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 August 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 Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 29/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 27/10

10:01 a.m.-10:36 p.m.

2 stops14h 35m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 29/9

5:45 p.m.-8:48 a.m.

2 stops13h 03m

Chicago Midway

Tue 27/10

12:27 p.m.-10:36 p.m.

2 stops12h 09m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 30/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 27/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 30/9

5:45 p.m.-8:48 a.m.

2 stops13h 03m

Chicago Midway

Tue 27/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 29/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Wed 28/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 29/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Wed 28/10

12:27 p.m.-10:59 p.m.

2 stops12h 32m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 30/9

5:45 p.m.-8:48 a.m.

2 stops13h 03m

Chicago Midway

Tue 27/10

12:27 p.m.-10:59 p.m.

2 stops12h 32m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 29/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 27/10

12:27 p.m.-8:33 p.m.

1 stop10h 06m

C$ 479

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 29/9

5:45 p.m.-8:48 a.m.

2 stops13h 03m

Chicago Midway

Wed 28/10

12:27 p.m.-10:36 p.m.

2 stops12h 09m

C$ 479
Quickest round-trip

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 15/9

6:00 a.m.-6:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 22/9

1:19 p.m.-9:10 p.m.

2 stops9h 51m

C$ 481

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 47m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 8h 47m
There are no direct flights from Vancouver to Chicago Midway Airport. There are no popular flight routes from Vancouver to Chicago Midway Airport.
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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 47m, 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
Valparaiso
Portage

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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