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Cheap flights from Vancouver 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 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
12:55 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
6:00 a.m. - 10:40 p.m.
MDW
-
YVR
18h 40m
2 stops
C$ 571Multiple Airlines
Thu, 12 Mar - Tue, 17 Mar
Multiple Airlines Logo
12:55 p.m. - 10:05 a.m.
YVR
-
MDW
19h 10m
1 stop
Multiple Airlines Logo
11:00 a.m. - 12:38 a.m.
MDW
-
YVR
15h 38m
1 stop
C$ 584Multiple Airlines
Thu, 5 Mar - Thu, 12 Mar
Multiple Airlines Logo
12:05 p.m. - 10:41 p.m.
YVR
-
MDW
8h 36m
1 stop
Multiple Airlines Logo
9:51 p.m. - 11:25 p.m.
MDW
-
YVR
27h 34m
2 stops
C$ 586Multiple Airlines
Sat, 7 Mar - Mon, 9 Mar
Multiple Airlines Logo
12:05 p.m. - 10:41 p.m.
YVR
-
MDW
8h 36m
1 stop
Multiple Airlines Logo
9:51 p.m. - 4:07 p.m.
MDW
-
YVR
20h 16m
2 stops
C$ 590Multiple Airlines
Sat, 7 Mar - Mon, 9 Mar

Delta flights from Vancouver to Chicago Midway Airport

Our best Delta deals on Vancouver 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
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
Delta
2 Mar
YVR7:37 p.m.Vancouver Intl
11h 17m
2 stops
MDW8:54 a.m.Chicago Midway
4 Mar
MDW9:34 a.m.Chicago Midway
16h 25m
2 stops
YVR11:59 p.m.Vancouver Intl
C$ 639

WestJet flights from Vancouver to Chicago Midway Airport

Our best WestJet deals on Vancouver to Chicago Midway Airport flight tickets
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$ 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
28 May
YVR5:30 p.m.Vancouver Intl
13h 13m
2 stops
MDW8:43 a.m.Chicago Midway
2 Jun
MDW9:22 a.m.Chicago Midway
11h 08m
2 stops
YVR6:30 p.m.Vancouver Intl
C$ 777

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 4 February 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

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

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 12/3

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

1 stop11h 35m

Chicago Midway

Tue 17/3

6:00 a.m.-10:40 p.m.

2 stops18h 40m

C$ 571

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.-12:38 a.m.

1 stop15h 38m

C$ 584

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 7/3

12:05 p.m.-10:41 p.m.

1 stop8h 36m

Chicago Midway

Mon 9/3

9:51 p.m.-11:25 p.m.

2 stops27h 34m

C$ 586

VancouverChicago

YVR - MDW

YVRMDW

Vancouver Intl

Sat 7/3

12:05 p.m.-10:41 p.m.

1 stop8h 36m

Chicago Midway

Mon 9/3

9:51 p.m.-4:07 p.m.

2 stops20h 16m

C$ 590

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 29m

Direct flights

None
The fastest flight from Vancouver to Chicago Midway Airport takes 8h 29m
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 2846.7 km apart from one another. Flights usually cover this in 8h 29m, 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.

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

    Confirm your travel details to search for the latest offers for flights from Vancouver to Chicago Midway Airport. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

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

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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?

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.

An easier way to manage your Chicago Midway Airport trip

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