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Cheap flights from Vancouver Intl Airport to Chicago from C$ 221

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 Intl Airport to Chicago departing on 24/4. 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

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Find the cheapest flights from Vancouver Intl Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:30 a.m. - 10:19 p.m.
YVR
-
MDW
10h 49m
1 stop
Multiple Airlines Logo
6:15 a.m. - 5:30 p.m.
MDW
-
YVR
13h 15m
2 stops
C$ 456Multiple Airlines
Sat, 2 May - Thu, 7 May
Multiple Airlines Logo
11:00 p.m. - 8:07 p.m.
YVR
-
MDW
19h 07m
1 stop
Multiple Airlines Logo
2:56 p.m. - 11:12 a.m.
MDW
-
YVR
22h 16m
1 stop
C$ 468Multiple Airlines
Wed, 8 Apr - Sun, 12 Apr
Multiple Airlines Logo
11:00 p.m. - 8:07 p.m.
YVR
-
MDW
19h 07m
1 stop
Multiple Airlines Logo
2:56 p.m. - 11:12 a.m.
MDW
-
YVR
22h 16m
1 stop
C$ 471Multiple Airlines
Wed, 8 Apr - Sun, 12 Apr
Multiple Airlines Logo
4:50 p.m. - 10:05 a.m.
YVR
-
MDW
15h 15m
1 stop
Multiple Airlines Logo
2:20 p.m. - 10:45 a.m.
MDW
-
YVR
22h 25m
1 stop
C$ 498Multiple Airlines
Sun, 26 Apr - Wed, 29 Apr
Multiple Airlines Logo
4:50 p.m. - 10:05 a.m.
YVR
-
MDW
15h 15m
1 stop
Multiple Airlines Logo
6:00 a.m. - 7:25 p.m.
MDW
-
YVR
15h 25m
2 stops
C$ 505Multiple Airlines
Sun, 26 Apr - Wed, 29 Apr
Multiple Airlines Logo
9:10 a.m. - 10:45 p.m.
YVR
-
MDW
11h 35m
1 stop
Multiple Airlines Logo
10:36 p.m. - 4:07 p.m.
MDW
-
YVR
43h 31m
2 stops
C$ 516Multiple Airlines
Thu, 26 Mar - Mon, 30 Mar
Multiple Airlines Logo
12:50 p.m. - 10:05 a.m.
YVR
-
MDW
19h 15m
1 stop
Multiple Airlines Logo
12:45 p.m. - 9:20 p.m.
MDW
-
YVR
10h 35m
2 stops
C$ 531Multiple Airlines
Wed, 22 Apr - Sat, 25 Apr
Multiple Airlines Logo
12:55 p.m. - 10:05 a.m.
YVR
-
MDW
19h 10m
1 stop
Multiple Airlines Logo
11:00 a.m. - 8:43 p.m.
MDW
-
YVR
11h 43m
2 stops
C$ 537Multiple Airlines
Thu, 5 Mar - Thu, 12 Mar
Multiple Airlines Logo
9:10 a.m. - 10:45 p.m.
YVR
-
MDW
11h 35m
1 stop
Multiple Airlines Logo
11:00 a.m. - 10:20 a.m.
MDW
-
YVR
25h 20m
1 stop
C$ 549Multiple Airlines
Thu, 26 Mar - Mon, 30 Mar
Multiple Airlines Logo
12:10 a.m. - 3:20 p.m.
YVR
-
MDW
13h 10m
1 stop
Multiple Airlines Logo
11:00 a.m. - 10:05 p.m.
MDW
-
YVR
13h 05m
1 stop
C$ 561Multiple Airlines
Thu, 9 Apr - Thu, 23 Apr

Delta flights from Vancouver Intl Airport to Chicago Midway Airport

Our best Delta deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
Delta
5 Mar
YVR6:20 a.m.Vancouver Intl
9h 17m
2 stops
MDW5:37 p.m.Chicago Midway
10 Mar
MDW1:10 p.m.Chicago Midway
12h 49m
2 stops
YVR11:59 p.m.Vancouver Intl
C$ 613
Delta
22 Apr
YVR7:30 p.m.Vancouver Intl
11h 17m
2 stops
MDW8:47 a.m.Chicago Midway
25 Apr
MDW9:27 a.m.Chicago Midway
13h 43m
2 stops
YVR9:10 p.m.Vancouver Intl
C$ 628
Delta
2 Mar
YVR7:37 p.m.Vancouver Intl
11h 17m
2 stops
MDW8:54 a.m.Chicago Midway
4 Mar
MDW1:29 p.m.Chicago Midway
12h 30m
2 stops
YVR11:59 p.m.Vancouver Intl
C$ 638

WestJet flights from Vancouver Intl Airport to Chicago Midway Airport

Our best WestJet deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
WestJet
25 Apr
YVR6:00 a.m.Vancouver Intl
25h 56m
2 stops
MDW9:56 a.m.Chicago Midway
28 Apr
MDW9:31 a.m.Chicago Midway
17h 14m
2 stops
YVR12:45 a.m.Vancouver Intl
C$ 767
WestJet
25 Apr
YVR5:00 p.m.Vancouver Intl
13h 47m
2 stops
MDW8:47 a.m.Chicago Midway
28 Apr
MDW9:27 a.m.Chicago Midway
13h 23m
2 stops
YVR8:50 p.m.Vancouver Intl
C$ 771
WestJet
25 Apr
YVR5:00 p.m.Vancouver Intl
13h 47m
2 stops
MDW8:47 a.m.Chicago Midway
28 Apr
MDW9:27 a.m.Chicago Midway
13h 23m
2 stops
YVR8:50 p.m.Vancouver Intl
C$ 777

momondo Fare Finder

 
Customize your flight search to find flights from Vancouver Intl Airport 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 February 2026.
Use the filters below to find and compare flights from Vancouver Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 2/5

9:30 a.m.-10:19 p.m.

1 stop10h 49m

Chicago Midway

Thu 7/5

6:15 a.m.-5:30 p.m.

2 stops13h 15m

C$ 456

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 8/4

11:00 p.m.-8:07 p.m.

1 stop19h 07m

Chicago Midway

Sun 12/4

2:56 p.m.-11:12 a.m.

1 stop22h 16m

C$ 468

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 8/4

11:00 p.m.-8:07 p.m.

1 stop19h 07m

Chicago Midway

Sun 12/4

2:56 p.m.-11:12 a.m.

1 stop22h 16m

C$ 471

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 26/4

4:50 p.m.-10:05 a.m.

1 stop15h 15m

Chicago Midway

Wed 29/4

2:20 p.m.-10:45 a.m.

1 stop22h 25m

C$ 498

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 26/4

4:50 p.m.-10:05 a.m.

1 stop15h 15m

Chicago Midway

Wed 29/4

6:00 a.m.-7:25 p.m.

2 stops15h 25m

C$ 505

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 26/3

9:10 a.m.-10:45 p.m.

1 stop11h 35m

Chicago Midway

Mon 30/3

10:36 p.m.-4:07 p.m.

2 stops43h 31m

C$ 516

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 22/4

12:50 p.m.-10:05 a.m.

1 stop19h 15m

Chicago Midway

Sat 25/4

12:45 p.m.-9:20 p.m.

2 stops10h 35m

C$ 531

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 5/3

12:55 p.m.-10:05 a.m.

1 stop19h 10m

Chicago Midway

Thu 12/3

11:00 a.m.-8:43 p.m.

2 stops11h 43m

C$ 537

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 26/3

9:10 a.m.-10:45 p.m.

1 stop11h 35m

Chicago Midway

Mon 30/3

11:00 a.m.-10:20 a.m.

1 stop25h 20m

C$ 549

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 9/4

12:10 a.m.-3:20 p.m.

1 stop13h 10m

Chicago Midway

Thu 23/4

11:00 a.m.-10:05 p.m.

1 stop13h 05m

C$ 561

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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When to book flights from Vancouver Intl Airport to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Vancouver Intl Airport to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Vancouver Intl Airport to Chicago Midway Airport (YVR to MDW) flight deals and tips

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

Fastest flight time

9h 17m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 9h 17m
There are no direct flights from Vancouver Intl Airport to Chicago Midway Airport. There are no popular flight routes from Vancouver Intl Airport to Chicago Midway Airport.
Search flight deals

  • How far is Vancouver Intl to Chicago Midway by plane?

    There are 2850.9 km between Vancouver Intl and Chicago Midway. In terms of flight time, this usually takes a little over 9h 17m.

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

    Prices for flights from Vancouver Intl Airport to Chicago Midway Airport were last updated today.

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Vancouver Intl Airport to Chicago Midway Airport.

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

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • How do I get Price Alerts for flights from Vancouver Intl Airport to Chicago Midway Airport?

    Search flight deals from Vancouver Intl Airport to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from Vancouver Intl Airport to Chicago Midway Airport with momondo?

    Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

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. 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?

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?

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.

An easier way to manage your Chicago Midway Airport trip

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