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

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

What cabin classes can I book on flights from Chicago Midway Airport to Winnipeg?

Only Economy Class is available on flights from Chicago Midway Airport to Winnipeg.

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

Connecting flights from Chicago Midway Airport to Winnipeg most commonly pass through: • Atlanta Hartsfield-Jackson (ATL) - 50% of one-stop connections • Minneapolis St Paul (MSP) - 50% of one-stop connections Together, these airports account for 100% of one-stop bookings on this route.

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

On the Chicago Midway Airport to Winnipeg route, being flexible with your departure day can save you up to 25%. Saturday is the cheapest day at $465 round-trip on average, while Thursday is the most expensive at $618: a $153 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

How long is a flight from Chicago Midway Airport to Winnipeg?

There are currently no nonstop flights available from Chicago Midway Airport to Winnipeg. Flights with 1 layover take between 5h 25m and 11h 44m in total, depending on the connection.

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

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 Chicago Midway Airport to Winnipeg 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 $366 to $1,991. That means the highest observed fare was about 5x higher than the lowest one.

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

One-way fares from Chicago Midway Airport to Winnipeg are currently higher than usual. Average one-way flight prices are about $206, which is 83% above the typical average for this route.

How much time can I save by choosing a different layover airport from Chicago Midway Airport to Winnipeg?

Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 5h 25m, compared with 11h 44m via Atlanta Hartsfield-Jackson (ATL).

What car rental options are available at Winnipeg Airport (YWG)?

Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates starting from around $18 for economy cars. Top options include: • Thrifty • Dollar • Hertz • Alamo • Fox

$145 CHEAP FLIGHTS from Chicago Midway to Winnipeg (MDW - YWG)

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Cheapest round-trip

$345

Typical prices: $465-$581

Multiple Airlines

Tue 10/9Fri 10/12

MDW - YWG • 1 stop

Cheapest one-way

$145

Typical prices: $112-$112

Porter Airlines

Thu 10/18

MDW - YWG • 2 stops

Top layover airports

Atlanta Hartsfield-Jackson (ATL)

Cheapest • Avg $247 (round-trip)

Minneapolis St Paul (MSP)

Shortest trip • 5h 25m (one-way)

Insights

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Flight Deals

Cheap Flights from Midway to Winnipeg (MDW-YWG)

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

Round-trip

One-way

Last minute

Recent round-trip flight deals from Midway to Winnipeg

Fri, Oct 9 - Mon, Oct 12

3:20 pm - 9:45 amMDW Chicago Midway-YWG Winnipeg

18h 25m1 stop Toronto Island

7:45 am - 11:00 amYWG Winnipeg-MDW Chicago Midway

27h 15m1 stop Toronto Pearson Intl

$345Multiple Airlines

Thu, Oct 1 - Sat, Oct 3

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

4:25 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

18h 35m1 stop Toronto Pearson Intl

$366Multiple Airlines

Fri, Oct 9 - Mon, Oct 12

3:20 pm - 9:45 amMDW Chicago Midway-YWG Winnipeg

18h 25m1 stop Toronto Island

9:05 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

17h 30m2 stops Calgary Toronto Pearson Intl

$375Multiple Airlines

Wed, Sep 30 - Fri, Oct 2

11:45 am - 8:40 amMDW Chicago Midway-YWG Winnipeg

20h 55m1 stop Toronto Island

5:10 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

17h 50m1 stop Toronto Pearson Intl

$389Multiple Airlines

Tue, Sep 29 - Sat, Oct 3

11:45 am - 12:55 amMDW Chicago Midway-YWG Winnipeg

13h 10m1 stop Toronto Island

4:25 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

18h 35m1 stop Toronto Pearson Intl

$425Multiple Airlines

Thu, Oct 1 - Fri, Oct 2

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

7:55 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

15h 05m1 stop Toronto Pearson Intl

$437Multiple Airlines

Tue, Sep 29 - Fri, Oct 2

3:20 pm - 12:55 amMDW Chicago Midway-YWG Winnipeg

9h 35m1 stop Toronto Island

5:10 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

21h 25m1 stop Toronto Pearson Intl

$448Multiple Airlines

Thu, Oct 1 - Sat, Oct 3

3:20 pm - 8:40 amMDW Chicago Midway-YWG Winnipeg

17h 20m1 stop Toronto Island

9:05 pm - 2:35 pmYWG Winnipeg-MDW Chicago Midway

17h 30m2 stops Calgary Toronto Pearson Intl

$453Multiple Airlines

Fri, Oct 9 - Mon, Oct 12

3:20 pm - 2:05 pmMDW Chicago Midway-YWG Winnipeg

22h 45m2 stops Toronto Island Calgary

9:05 pm - 11:00 amYWG Winnipeg-MDW Chicago Midway

13h 55m2 stops Calgary Toronto Pearson Intl

$458Multiple Airlines

Tue, Sep 29 - Sat, Oct 3

3:20 pm - 12:15 pmMDW Chicago Midway-YWG Winnipeg

20h 55m2 stops Toronto Island Calgary

6:15 am - 2:35 pmYWG Winnipeg-MDW Chicago Midway

8h 20m1 stop Toronto Pearson Intl

$471Multiple Airlines

Booking Insights

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

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

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

Atlanta Hartsfield-Jackson (ATL) and Minneapolis St Paul (MSP) are the most popular layovers for the Chicago Midway Airport to Winnipeg route. 50% of KAYAK users who booked 1-stop round-trips over the past 3 months connected via ATL or MSP.

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

Flights via Atlanta Hartsfield-Jackson (ATL) offer the most affordable fares, with an average round-trip price of $247. Based on KAYAK data over the past 3 months.

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

Minneapolis St Paul (MSP) had the shortest average connection time for Chicago Midway Airport to Winnipeg layovers at 224 minutes over the past 3 months.

Find deals

Cheapest flight	$145

Flight from Chicago Midway Airport to Winnipeg

When to book flights from Midway to Winnipeg

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

Estimated round-trip price

KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

Which airports can I use when flying from Chicago Midway Airport to Winnipeg?
Flights from Chicago Midway Airport to Winnipeg usually depart from Chicago Midway (MDW) and arrive at Winnipeg (YWG).
What cabin classes can I book on flights from Chicago Midway Airport to Winnipeg?
Only Economy Class is available on flights from Chicago Midway Airport to Winnipeg.
Which airports do connecting flights from Chicago Midway Airport to Winnipeg pass through?
Connecting flights from Chicago Midway Airport to Winnipeg most commonly pass through:

• Atlanta Hartsfield-Jackson (ATL) - 50% of one-stop connections
• Minneapolis St Paul (MSP) - 50% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.
Can I save money by using flexible dates for flights from Chicago Midway Airport to Winnipeg?
On the Chicago Midway Airport to Winnipeg route, being flexible with your departure day can save you up to 25%. Saturday is the cheapest day at $465 round-trip on average, while Thursday is the most expensive at $618: a $153 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.
How long is a flight from Chicago Midway Airport to Winnipeg?
There are currently no nonstop flights available from Chicago Midway Airport to Winnipeg. Flights with 1 layover take between 5h 25m and 11h 44m in total, depending on the connection.
Do I need a passport to fly from Chicago Midway Airport to Winnipeg?
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 Chicago Midway Airport to Winnipeg 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 $366 to $1,991. That means the highest observed fare was about 5x higher than the lowest one.
How are flight prices from Chicago Midway Airport to Winnipeg looking right now?
One-way fares from Chicago Midway Airport to Winnipeg are currently higher than usual. Average one-way flight prices are about $206, which is 83% above the typical average for this route.
How much time can I save by choosing a different layover airport from Chicago Midway Airport to Winnipeg?
Flying via Minneapolis St Paul (MSP) gives the shortest average 1-stop total travel time at 5h 25m, compared with 11h 44m via Atlanta Hartsfield-Jackson (ATL).
What car rental options are available at Winnipeg Airport (YWG)?
Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates starting from around $18 for economy cars. Top options include:
• Thrifty
• Dollar
• Hertz
• Alamo
• Fox

If your dates can be flexible, aim for a Saturday departure instead of Thursday. On this route, Saturday flights average $465 - about $153 less than Thursday (25% savings) based on the last 12 months.
If you're arriving late at night and need somewhere to stay, check out these hotels close to Winnipeg Airport.
- Victoria Inn Hotel & Convention Centre
- Lakeview Signature, Trademark Collection by Wyndham
- Days Inn and Suites Winnipeg Airport, Manitoba

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$145 Find Cheap Flights from Chicago Midway Airport to Winnipeg - Compare and Save

Everything you should know

Cheap Flights from Midway to Winnipeg (MDW-YWG)

Recent round-trip flight deals from Midway to Winnipeg

Recent one-way flight deals from Midway to Winnipeg

Recent last minute flight deals from Midway to Winnipeg

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

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

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

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

Key details for Chicago Midway Airport to Winnipeg flights

Cheapest flight

When to book flights from Midway to Winnipeg

Your Chicago Midway Airport to Winnipeg flight questions, answered

Your guide to booking Chicago Midway Airport to Winnipeg flights

More options for your flight from Midway to Winnipeg

Complete your trip to Winnipeg with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights to Winnipeg

Find direct flights to and from Midway and Winnipeg

Flights from domestic origins to Winnipeg

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