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Cheap flights from Vancouver Intl Airport to Chicago from C$ 203

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 4/2. 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
11:00 p.m. - 10:19 p.m.
YVR
-
MDW
21h 19m1 stop
Multiple Airlines Logo
5:01 p.m. - 11:12 a.m.
MDW
-
YVR
20h 11m1 stop
C$ 385Multiple Airlines
Sun, 18 Jan - Sun, 25 Jan
Multiple Airlines Logo
10:05 p.m. - 2:26 p.m.
YVR
-
MDW
14h 21m2 stops
Multiple Airlines Logo
11:05 a.m. - 10:20 a.m.
MDW
-
YVR
25h 15m1 stop
C$ 402Multiple Airlines
Wed, 18 Feb - Tue, 24 Feb
Multiple Airlines Logo
11:00 p.m. - 11:27 a.m.
YVR
-
MDW
10h 27m1 stop
Multiple Airlines Logo
11:05 a.m. - 10:20 a.m.
MDW
-
YVR
25h 15m1 stop
C$ 414Multiple Airlines
Wed, 18 Feb - Tue, 24 Feb
Multiple Airlines Logo
7:45 p.m. - 11:45 a.m.
YVR
-
MDW
14h 00m2 stops
Multiple Airlines Logo
5:01 p.m. - 11:12 a.m.
MDW
-
YVR
20h 11m1 stop
C$ 415Multiple Airlines
Thu, 22 Jan - Sun, 25 Jan
Delta Logo
7:37 p.m. - 8:52 a.m.
YVR
-
MDW
11h 15m2 stops
Delta Logo
1:49 p.m. - 11:59 p.m.
MDW
-
YVR
12h 10m2 stops
C$ 432Delta
Fri, 23 Jan - Wed, 28 Jan
Delta Logo
3:30 p.m. - 8:52 a.m.
YVR
-
MDW
15h 22m2 stops
Delta Logo
9:33 a.m. - 10:47 a.m.
MDW
-
YVR
27h 14m2 stops
C$ 433Delta
Thu, 29 Jan - Sun, 1 Feb
Multiple Airlines Logo
12:20 p.m. - 10:10 a.m.
YVR
-
MDW
19h 50m2 stops
Multiple Airlines Logo
5:01 p.m. - 11:12 a.m.
MDW
-
YVR
20h 11m1 stop
C$ 436Multiple Airlines
Sun, 18 Jan - Sun, 25 Jan
Multiple Airlines Logo
11:00 p.m. - 11:45 a.m.
YVR
-
MDW
10h 45m1 stop
Multiple Airlines Logo
5:01 p.m. - 2:45 p.m.
MDW
-
YVR
23h 44m2 stops
C$ 439Multiple Airlines
Wed, 21 Jan - Mon, 26 Jan
Multiple Airlines Logo
12:20 p.m. - 10:10 a.m.
YVR
-
MDW
19h 50m2 stops
Multiple Airlines Logo
7:30 a.m. - 11:59 p.m.
MDW
-
YVR
18h 29m1 stop
C$ 451Multiple Airlines
Sun, 1 Feb - Fri, 6 Feb
Multiple Airlines Logo
9:10 a.m. - 11:41 p.m.
YVR
-
MDW
12h 31m1 stop
Multiple Airlines Logo
3:26 p.m. - 10:38 p.m.
MDW
-
YVR
33h 12m2 stops
C$ 464Multiple Airlines
Thu, 12 Feb - Sun, 15 Feb

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
23 Jan
YVR7:37 p.m.Vancouver Intl
11h 15m
2 stops
MDW8:52 a.m.Chicago Midway
28 Jan
MDW1:49 p.m.Chicago Midway
12h 10m
2 stops
YVR11:59 p.m.Vancouver Intl
C$ 432
Find similar
Delta
29 Jan
YVR3:30 p.m.Vancouver Intl
15h 22m
2 stops
MDW8:52 a.m.Chicago Midway
1 Feb
MDW9:33 a.m.Chicago Midway
27h 14m
2 stops
YVR10:47 a.m.Vancouver Intl
C$ 433
Find similar
Delta
4 Feb
YVR7:37 p.m.Vancouver Intl
11h 15m
2 stops
MDW8:52 a.m.Chicago Midway
11 Feb
MDW12:46 p.m.Chicago Midway
13h 13m
2 stops
YVR11:59 p.m.Vancouver Intl
C$ 487
Find similar

Porter Airlines flights from Vancouver Intl Airport to Chicago Midway Airport

Our best Porter Airlines deals on Vancouver Intl Airport to Chicago Midway Airport flight tickets
Porter Airlines
8 Jan
YVR12:20 p.m.Vancouver Intl
19h 50m
2 stops
MDW10:10 a.m.Chicago Midway
15 Jan
MDW11:05 a.m.Chicago Midway
12h 20m
2 stops
YVR9:25 p.m.Vancouver Intl
C$ 552
Find similar
Porter Airlines
16 Feb
YVR12:20 p.m.Vancouver Intl
19h 45m
2 stops
MDW10:05 a.m.Chicago Midway
20 Feb
MDW11:00 a.m.Chicago Midway
12h 25m
2 stops
YVR9:25 p.m.Vancouver Intl
C$ 593
Find similar
Porter Airlines
30 Dec
YVR8:30 a.m.Vancouver Intl
23h 35m
2 stops
MDW10:05 a.m.Chicago Midway
3 Jan
MDW11:05 a.m.Chicago Midway
15h 43m
2 stops
YVR12:48 a.m.Vancouver Intl
C$ 1,202
Find similar

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 21 December 2025.
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

Sun 18/1

11:00 p.m.-10:19 p.m.

1 stop21h 19m

Chicago Midway

Sun 25/1

5:01 p.m.-11:12 a.m.

1 stop20h 11m

C$ 385

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 18/2

10:05 p.m.-2:26 p.m.

2 stops14h 21m

Chicago Midway

Tue 24/2

11:05 a.m.-10:20 a.m.

1 stop25h 15m

C$ 402

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 18/2

11:00 p.m.-11:27 a.m.

1 stop10h 27m

Chicago Midway

Tue 24/2

11:05 a.m.-10:20 a.m.

1 stop25h 15m

C$ 414

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 22/1

7:45 p.m.-11:45 a.m.

2 stops14h 00m

Chicago Midway

Sun 25/1

5:01 p.m.-11:12 a.m.

1 stop20h 11m

C$ 415

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Fri 23/1

7:37 p.m.-8:52 a.m.

2 stops11h 15m

Chicago Midway

Wed 28/1

1:49 p.m.-11:59 p.m.

2 stops12h 10m

C$ 432

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 29/1

3:30 p.m.-8:52 a.m.

2 stops15h 22m

Chicago Midway

Sun 1/2

9:33 a.m.-10:47 a.m.

2 stops27h 14m

C$ 433

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 18/1

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

2 stops19h 50m

Chicago Midway

Sun 25/1

5:01 p.m.-11:12 a.m.

1 stop20h 11m

C$ 436

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Wed 21/1

11:00 p.m.-11:45 a.m.

1 stop10h 45m

Chicago Midway

Mon 26/1

5:01 p.m.-2:45 p.m.

2 stops23h 44m

C$ 439

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sun 1/2

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

2 stops19h 50m

Chicago Midway

Fri 6/2

7:30 a.m.-11:59 p.m.

1 stop18h 29m

C$ 451

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Thu 12/2

9:10 a.m.-11:41 p.m.

1 stop12h 31m

Chicago Midway

Sun 15/2

3:26 p.m.-10:38 p.m.

2 stops33h 12m

C$ 464

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

8h 05m

Direct flights

None
The fastest flight from Vancouver Intl Airport to Chicago Midway Airport takes 8h 05m
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 8h 05m.

  • 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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