YWG - MDW

$222 Find Cheap Flights from Winnipeg to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$439
Typical prices: $434-$853
Multiple Airlines
Thu 2/1Sun 2/4
YWG - MDW • 1 stop
Cheapest one-way
$222
Typical prices: $198-$647
Multiple Airlines
Tue 12/11
YWG - MDW • 2 stops
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Flight Deals

Cheap Flights from Winnipeg to Midway (YWG-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Midway

Mon, Feb 1 - Thu, Feb 4
Multiple Airlines Logo
7:00 am - 11:46 pmYWG  Winnipeg-MDW Chicago Midway
17h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:18 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
24h 22m1 stop Atlanta Hartsfield-Jackson
$439Multiple Airlines
Fri, Jan 22 - Tue, Jan 26
Multiple Airlines Logo
7:00 am - 11:46 pmYWG  Winnipeg-MDW Chicago Midway
17h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:18 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
24h 22m1 stop Atlanta Hartsfield-Jackson
$443Multiple Airlines
Wed, Feb 3 - Sun, Feb 7
Multiple Airlines Logo
7:00 am - 11:46 pmYWG  Winnipeg-MDW Chicago Midway
17h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:18 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
24h 22m1 stop Atlanta Hartsfield-Jackson
$444Multiple Airlines
Fri, Jan 22 - Mon, Jan 25
Multiple Airlines Logo
7:00 am - 11:46 pmYWG  Winnipeg-MDW Chicago Midway
17h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
1:18 pm - 5:25 pmMDW  Chicago Midway-YWG Winnipeg
27h 07m2 stops Atlanta Hartsfield-Jackson Calgary
$494Multiple Airlines
Mon, Feb 1 - Thu, Feb 4
Multiple Airlines Logo
7:00 am - 11:46 pmYWG  Winnipeg-MDW Chicago Midway
17h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:47 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
16h 53m2 stops Orlando Atlanta Hartsfield-Jackson
$495Multiple Airlines
Thu, Dec 3 - Thu, Dec 10
Multiple Airlines Logo
9:35 pm - 4:07 pmYWG  Winnipeg-MDW Chicago Midway
19h 32m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 pm - 5:25 pmMDW  Chicago Midway-YWG Winnipeg
23h 23m2 stops Atlanta Hartsfield-Jackson Calgary
$497Multiple Airlines
Wed, Feb 3 - Sun, Feb 7
Multiple Airlines Logo
7:00 am - 11:46 pmYWG  Winnipeg-MDW Chicago Midway
17h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:47 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
16h 53m2 stops Orlando Atlanta Hartsfield-Jackson
$500Multiple Airlines
Fri, Jan 22 - Tue, Jan 26
Multiple Airlines Logo
7:00 am - 7:42 pmYWG  Winnipeg-MDW Chicago Midway
13h 42m2 stops Atlanta Hartsfield-Jackson Orlando
Multiple Airlines Logo
1:18 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
24h 22m1 stop Atlanta Hartsfield-Jackson
$501Multiple Airlines
Mon, Nov 16 - Mon, Nov 23
Multiple Airlines Logo
9:35 pm - 11:47 pmYWG  Winnipeg-MDW Chicago Midway
27h 12m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:42 pm - 5:30 pmMDW  Chicago Midway-YWG Winnipeg
19h 48m1 stop Orlando
$564Multiple Airlines
Fri, Jan 22 - Mon, Jan 25
Multiple Airlines Logo
7:00 am - 11:46 pmYWG  Winnipeg-MDW Chicago Midway
17h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:47 pm - 5:30 pmMDW  Chicago Midway-YWG Winnipeg
19h 43m1 stop Orlando
$631Multiple Airlines
Booking Insights

Price, demand and travel trends for Winnipeg to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What is the cheapest layover airport when flying from Winnipeg to Chicago Midway Airport?

Flights via Minneapolis St Paul (MSP) offer the most affordable fares, with an average round-trip price of $697. Based on KAYAK data over the past 3 months.

When flying from Winnipeg to Chicago Midway Airport which airport offers the shortest layover?

Minneapolis St Paul (MSP) had the shortest average connection time for Winnipeg to Chicago Midway Airport layovers at 3h 45m over the past 3 months.

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Key details for Winnipeg to Chicago Midway Airport flights

Cheapest flight

$222
One-way flight from Winnipeg to Chicago Midway Airport

When to book flights from Winnipeg to Midway

Are your dates flexible? Find out the best times to travel from Winnipeg to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Winnipeg to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Do I need a passport to fly from Winnipeg to Chicago Midway Airport?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Winnipeg to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $439 to $1,669. That means the highest observed fare was about 4x higher than the lowest one.

  • How are flight prices from Winnipeg to Chicago Midway Airport looking right now?

    One-way fares from Winnipeg to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $278, which is 36% below the typical average for this route.

  • Which airports can I use when flying from Winnipeg to Chicago Midway Airport?

    Flights from Winnipeg to Chicago Midway Airport usually depart from Winnipeg (YWG) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Winnipeg to Chicago Midway Airport pass through?

    Most connecting flights from Winnipeg to Chicago Midway Airport pass through Minneapolis St Paul (MSP), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Winnipeg to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 62% on flights from Winnipeg to Chicago Midway Airport. Friday is the cheapest departure day at $327 round-trip on average, while Wednesday is the most expensive at $853, a difference of $526.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking Winnipeg to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.

More options for your flight from Winnipeg to Midway

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