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Cheap flights from Vancouver to Chicago from $200

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 9/4. 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 am - 4:47 pmYVR  Vancouver Intl-MDW Chicago Midway
8h 47m1 stop Minneapolis St Paul
Delta Logo
12:27 pm - 8:33 pmMDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
$347Delta
Tue, Oct 6 - Sat, Oct 10
Delta Logo
6:00 am - 6:19 pmYVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 pm - 8:33 pmMDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
$359Delta
Sun, Oct 4 - Sat, Oct 10
Delta Logo
6:00 am - 6:19 pmYVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
12:27 pm - 8:33 pmMDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
$369Delta
Thu, Oct 1 - Thu, Oct 8
Delta Logo
7:30 pm - 8:48 amYVR  Vancouver Intl-MDW Chicago Midway
11h 18m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
2:00 pm - 8:26 pmMDW  Chicago Midway-YVR Vancouver Intl
8h 26m1 stop Minneapolis St Paul
$374Delta
Wed, Sep 30 - Sat, Oct 3
Delta Logo
6:00 am - 6:19 pmYVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
2:00 pm - 8:26 pmMDW  Chicago Midway-YVR Vancouver Intl
8h 26m1 stop Minneapolis St Paul
$374Delta
Wed, Sep 30 - Sat, Oct 3
Delta Logo
6:00 am - 4:47 pmYVR  Vancouver Intl-MDW Chicago Midway
8h 47m1 stop Minneapolis St Paul
Delta Logo
1:27 pm - 9:13 pmMDW  Chicago Midway-YVR Vancouver Intl
9h 46m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$378Delta
Tue, Oct 6 - Wed, Oct 14
Delta Logo
7:00 am - 3:47 pmYVR  Vancouver Intl-MDW Chicago Midway
7h 47m1 stop Minneapolis St Paul
Delta Logo
12:30 pm - 12:59 amMDW  Chicago Midway-YVR Vancouver Intl
13h 29m2 stops Minneapolis St Paul Seattle/Tacoma Intl
$383Delta
Wed, Nov 4 - Wed, Nov 11
Delta Logo
6:00 am - 6:19 pmYVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
Delta Logo
1:27 pm - 9:13 pmMDW  Chicago Midway-YVR Vancouver Intl
9h 46m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$384Delta
Wed, Sep 30 - Wed, Oct 7
WestJet Logo
6:05 am - 6:24 pmYVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
WestJet Logo
2:05 pm - 8:31 pmMDW  Chicago Midway-YVR Vancouver Intl
8h 26m1 stop Minneapolis St Paul
$463WestJet
Wed, Sep 9 - Wed, Sep 16
WestJet Logo
6:05 am - 6:24 pmYVR  Vancouver Intl-MDW Chicago Midway
10h 19m1 stop Minneapolis St Paul
WestJet Logo
12:32 pm - 8:38 pmMDW  Chicago Midway-YVR Vancouver Intl
10h 06m1 stop Minneapolis St Paul
$547WestJet
Wed, Sep 30 - Wed, Oct 7

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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
Oct 6
YVR6:00 amVancouver Intl
8h 47m
1 stop
MDW4:47 pmChicago Midway
Oct 10
MDW12:27 pmChicago Midway
10h 06m
1 stop
YVR8:33 pmVancouver Intl
$347
Delta
Oct 4
YVR6:00 amVancouver Intl
10h 19m
1 stop
MDW6:19 pmChicago Midway
Oct 10
MDW12:27 pmChicago Midway
10h 06m
1 stop
YVR8:33 pmVancouver Intl
$359
Delta
Oct 1
YVR6:00 amVancouver Intl
10h 19m
1 stop
MDW6:19 pmChicago Midway
Oct 8
MDW12:27 pmChicago Midway
10h 06m
1 stop
YVR8:33 pmVancouver Intl
$369

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets
WestJet
Aug 21
YVR6:00 amVancouver Intl
10h 01m
2 stops
MDW6:01 pmChicago Midway
Sep 9
MDW9:59 amChicago Midway
36h 51m
2 stops
YVR8:50 pmVancouver Intl
$829
WestJet
Aug 21
YVR8:30 amVancouver Intl
26h 40m
2 stops
MDW1:10 pmChicago Midway
Sep 9
MDW7:13 pmChicago Midway
41h 17m
2 stops
YVR10:30 amVancouver Intl
$833
WestJet
Aug 25
YVR6:00 amVancouver Intl
10h 01m
1 stop
MDW6:01 pmChicago Midway
Sep 4
MDW12:46 pmChicago Midway
23h 59m
1 stop
YVR10:45 amVancouver Intl
$924

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 832,500 searches. Data last updated August 18, 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 10/6

6:00 am-4:47 pm

1 stop8h 47m

Chicago Midway

Sat 10/10

12:27 pm-8:33 pm

1 stop10h 06m

$347

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Sun 10/4

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Sat 10/10

12:27 pm-8:33 pm

1 stop10h 06m

$359

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Thu 10/1

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Thu 10/8

12:27 pm-8:33 pm

1 stop10h 06m

$369

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 9/30

7:30 pm-8:48 am

2 stops11h 18m

Chicago Midway

Sat 10/3

2:00 pm-8:26 pm

1 stop8h 26m

$374

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 9/30

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Sat 10/3

2:00 pm-8:26 pm

1 stop8h 26m

$374
Quickest round-trip

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Tue 10/6

6:00 am-4:47 pm

1 stop8h 47m

Chicago Midway

Wed 10/14

1:27 pm-9:13 pm

2 stops9h 46m

$378

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 11/4

7:00 am-3:47 pm

1 stop7h 47m

Chicago Midway

Wed 11/11

12:30 pm-12:59 am

2 stops13h 29m

$383

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 9/30

6:00 am-6:19 pm

1 stop10h 19m

Chicago Midway

Wed 10/7

1:27 pm-9:13 pm

2 stops9h 46m

$384

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 9/9

6:05 am-6:24 pm

1 stop10h 19m

Chicago Midway

Wed 9/16

2:05 pm-8:31 pm

1 stop8h 26m

$463

VancouverChicago

YVR Vancouver Intl - MDW Chicago Midway

YVRMDW

Vancouver Intl

Wed 9/30

6:05 am-6:24 pm

1 stop10h 19m

Chicago Midway

Wed 10/7

12:32 pm-8:38 pm

1 stop10h 06m

$547

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

Best Price Found

$200

Fastest flight time

9h 00m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Vancouver in the past 72 hours is $200. The best round-trip flight deal from Vancouver to Chicago Midway Airport found on momondo in the last 72 hours is $347.
The fastest flight from Vancouver to Chicago Midway Airport takes 9h 00m
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?

    The straight-line distance from Vancouver to Chicago Midway is 1768.8 mi. 9h 00m is a normal flight duration for this route.

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

    Prices for flights from Vancouver to Chicago Midway Airport are updated daily.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

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. momondo enables you to select and highlight flights to Chicago from Vancouver with this policy.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Vancouver and alert you when they change.

An easier way to manage your Chicago Midway Airport trip

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