AED 883 Cheap flights from Vancouver to Chicago Midway

Compare Vancouver to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Vancouver to Chicago Midway

Looking for a cheap last-minute deal or the best round-trip flight from Vancouver to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.

Chicago.AED 883 per passenger.Departing Thu, Feb 19, returning Sun, Feb 22.Round-trip flight with WestJet and Frontier Airlines.Outbound indirect flight with WestJet, departing from Vancouver International on Thu, Feb 19, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Sun, Feb 22, arriving in Vancouver International.Price includes taxes and charges.From AED 883, select.

Chicago.AED 986 per passenger.Departing Sat, Jan 31, returning Fri, Feb 6.Round-trip flight with WestJet and Frontier Airlines.Outbound indirect flight with WestJet, departing from Vancouver International on Sat, Jan 31, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Fri, Feb 6, arriving in Vancouver International.Price includes taxes and charges.From AED 986, select.

Chicago.AED 1,006 per passenger.Departing Wed, Jan 21, returning Wed, Jan 28.Round-trip flight with WestJet and Frontier Airlines.Outbound indirect flight with WestJet, departing from Vancouver International on Wed, Jan 21, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Wed, Jan 28, arriving in Vancouver International.Price includes taxes and charges.From AED 1,006, select.

Chicago.AED 1,086 per passenger.Departing Thu, Mar 5, returning Mon, Mar 9.Round-trip flight with Porter Airlines and Frontier Airlines.Outbound indirect flight with Porter Airlines, departing from Vancouver International on Thu, Mar 5, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Mon, Mar 9, arriving in Vancouver International.Price includes taxes and charges.From AED 1,086, select.

Chicago.AED 1,426 per passenger.Departing Thu, Feb 12, returning Tue, Mar 3.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Vancouver International on Thu, Feb 12, arriving in Chicago Midway.Inbound indirect flight with WestJet, departing from Chicago Midway on Tue, Mar 3, arriving in Vancouver International.Price includes taxes and charges.From AED 1,426, select.

Chicago.AED 1,495 per passenger.Departing Fri, Apr 10, returning Mon, Apr 13.Round-trip flight with WestJet and Frontier Airlines.Outbound indirect flight with WestJet, departing from Vancouver International on Fri, Apr 10, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago Midway on Mon, Apr 13, arriving in Vancouver International.Price includes taxes and charges.From AED 1,495, select.

Chicago.AED 1,608 per passenger.Departing Sat, Oct 10, returning Wed, Oct 14.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Vancouver International on Sat, Oct 10, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Wed, Oct 14, arriving in Vancouver International.Price includes taxes and charges.From AED 1,608, select.

Chicago.AED 1,807 per passenger.Departing Wed, Apr 29, returning Mon, May 4.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Vancouver International on Wed, Apr 29, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Mon, May 4, arriving in Vancouver International.Price includes taxes and charges.From AED 1,807, select.

Find the cheapest month to fly from Vancouver to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Vancouver to Chicago Midway flights are currently cheapest in February.

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Vancouver to Chicago Midway: Alternative routes

Compare routes from Vancouver to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Vancouver to Chicago: Flight information

The things to know before you go.

Cheapest flight found	AED 883
Cheapest month to fly	February

Finding cheap flights from Vancouver to Chicago Midway: Frequently asked questions

How much are round-trip flights from Vancouver to Chicago Midway?

The best price we found for a round-trip flight from Vancouver to Chicago Midway is AED 883. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Vancouver to Chicago Midway?

Currently, there are no airlines that fly direct from Vancouver to Chicago Midway. But we found flights with one stop from AED 883.

How many flights are there a week from Vancouver to Chicago Midway?

There are no flights flying from Vancouver to Chicago Midway, as of December 2025.

When is the cheapest time to fly from Vancouver to Chicago Midway?

The cheapest month to fly from Vancouver to Chicago Midway is usually February.

Which upcoming date is cheapest to fly from Vancouver to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Vancouver to Chicago Midway Airport on Thursday, February 19, 2026.

Can I get a direct flight from Vancouver to Chicago Midway Airport?

No airlines currently offer direct flights between Vancouver and Chicago Midway Airport. Most routes have one or more stops.

How can I find the best flight deal to Chicago Midway?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly with from Vancouver to Chicago Midway?

The cheapest airline that flies to Chicago Midway is WestJet.

Traveling from Vancouver to Chicago Midway International Airport (MDW): What you need to know

You can choose from a range of airports when organizing your flight from Vancouver to Chicago Midway International Airport (MDW). Explore your options for jetting out of Vancouver International Airport (YVR), Vancouver Harbour Sea Plane Base Airport (CXH) and Abbotsford Airport (YXX).
The timezone in Chicago is UTC-5, which is two hours ahead of Vancouver. Chicago Midway International Airport is located in Chicago.
To ensure you get on your flight from Vancouver to MDW, leave enough time for things like check-in and baggage drop. Arriving two hours before international departures and an hour before domestic flights is the general rule.
Longer lines at security and check-in are more likely if you're heading away during high season, so give yourself some extra breathing space. The recommendation for peak times? Arrive up to four hours ahead for international flights and two hours for domestic departures.

Airports in Vancouver

Vancouver International Airport (YVR)

The journey from central Vancouver to YVR takes around 35 minutes by public transport. If you ride-share, drive or get a cab, you'll cover the 14 kilometers in 25 minutes or so, depending on traffic conditions.
Planning to catch an early flight from Vancouver to Chicago Midway International Airport? Avoid the hassle of rushing to the terminal (and get some extra shut-eye) by picking one of these hotels near Vancouver International Airport:
Of all flights leaving Vancouver International Airport, 71.77% arrive as scheduled at their destination.

Vancouver Harbour Sea Plane Base Airport (CXH)

You can get to CXH from the center of Vancouver in about 5 minutes by car (depending on traffic conditions). The ride on public transport will take roughly 15 minutes to travel the 2 kilometers or so.
Want to treat yourself to an extra night away before boarding your Vancouver to MDW flight? Check in to a hotel near Vancouver Harbour Sea Plane Base Airport before your adventure officially begins. These stays have your key waiting:

Abbotsford Airport (YXX)

YXX is around 64 kilometers from central Vancouver. Driving from the city center to the airport takes about 1 hour. If you're considering public transport, expect a journey of around 1 hour 30 minutes.
Make catching an early Vancouver to Chicago Midway International Airport flight the easiest part of your journey. Stay at one of these accommodation options close to Abbotsford Airport and get to your boarding gate with plenty of time to spare:
Flights departing from YXX arrive at their destination within the expected time frame 67.97% of the time.

About Chicago Midway International Airport (MDW)

If you have a late flight from Vancouver to Chicago Midway International Airport, nothing beats the convenience of staying close to the terminal. Grab your bags from the carousel and then be showered and sleeping not long after at one of these hotels near MDW:
Go where the road takes you with a Chicago Midway International Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and chase adventure across Chicago and beyond.
Booking your ride around four weeks in advance of your Vancouver to Chicago Midway International Airport flight can help you secure the lowest rate.
MDW is located at 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

Chicago Midway International Airport is about 14 kilometers from central Chicago. The time it takes to get to the center in a car rental or cab depends on the time of day. Do a little research before your trip.
Traveling by public transport takes about 45 minutes.

How to find the cheapest flights from Vancouver to Chicago Midway International Airport (MDW)

The cheapest price we've found for a one-way ticket from Vancouver to Chicago Midway International Airport is AED 420. For a return flight on this route, the best price is AED 883. Depending on how early you book and the availability, these fares can change.
To find cheap flights from Vancouver to MDW, book early. Airlines generally offer lower fares when flights first go on sale.
If you're flexible with your trip dates, use the 'Whole month' tool. It'll show you the lowest price across every month when searching for your Vancouver to Chicago Midway International Airport ticket.
Snapping up a cheap flight ticket from Vancouver to MDW is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll notify you when the price has dropped.
Filters make it easier to scoop up a deal on your flight from Vancouver to Chicago Midway International Airport. Pick the departure times, carriers and stops that match your plans. Then sort the results by 'Cheapest' to find the most affordable option fast.

The best time to fly from Vancouver to Chicago Midway International Airport (MDW)

July is the busiest month for flights from Vancouver to Chicago Midway International Airport (MDW). Plan your visit to Chicago in May if you'd rather avoid peak season.
Book a Vancouver to MDW flight ticket departing in July if you're eager to explore the city during its warmest month. Expect temperatures in Chicago to range from 15ºC (59ºF) to 29ºC (84ºF).
Look for cheap tickets from Vancouver to Chicago Midway International Airport in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

When it comes to looking for somewhere to lay your head, you'll find the best places to stay in Chicago right here. Browse these hotels once you've booked your flight from Vancouver to Chicago Midway International Airport:
Your Chicago visit wouldn't be complete without a bit of sightseeing. Top attractions you can't miss include Millennium Park, Lollapalooza and Art Institute of Chicago.

Explore more of the United States

Chicago has loads to offer, but there are so many other corners of the United States you'll want to see. About 257 kilometers south-east of Chicago, a visit to Indianapolis will fill your itinerary to the brim. Start with attractions like 9-11 Memorial, Lucas Oil Stadium and Eiteljorg Museum.
If there's time to check out another side of the United States, head for Milwaukee, roughly 137 kilometers north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are among its highlights.