YWG - MDW

$239 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
$401
Typical prices: $434-$434
Multiple Airlines
Mon 10/1Thu 10/4
YWG - MDW • 1 stop
Cheapest one-way
$239
Typical prices: $198-$647
Porter Airlines
Fri 10/5
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

Thu, Oct 1 - Sun, Oct 4
Multiple Airlines Logo
6:05 pm - 2:35 pmYWG  Winnipeg-MDW Chicago Midway
20h 30m1 stop Toronto Pearson Intl
Multiple Airlines Logo
11:45 am - 9:45 amMDW  Chicago Midway-YWG Winnipeg
22h 00m1 stop Toronto Island
$401Multiple Airlines
Sat, Sep 26 - Wed, Sep 30
Delta Logo
12:41 pm - 5:59 pmYWG  Winnipeg-MDW Chicago Midway
5h 18m1 stop Minneapolis St Paul
Delta Logo
1:19 pm - 3:08 pmMDW  Chicago Midway-YWG Winnipeg
25h 49m2 stops Detroit Metropolitan Wayne County Minneapolis St Paul
$563Delta
Thu, Oct 1 - Sun, Oct 4
Multiple Airlines Logo
8:45 pm - 11:00 amYWG  Winnipeg-MDW Chicago Midway
14h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 12:55 amMDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
$583Multiple Airlines
Sat, Sep 26 - Wed, Sep 30
Delta Logo
12:41 pm - 5:59 pmYWG  Winnipeg-MDW Chicago Midway
5h 18m1 stop Minneapolis St Paul
Delta Logo
5:11 pm - 3:08 pmMDW  Chicago Midway-YWG Winnipeg
21h 57m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul
$585Delta
Tue, Nov 24 - Wed, Dec 2
WestJet Logo
5:00 am - 6:04 pmYWG  Winnipeg-MDW Chicago Midway
13h 04m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
WestJet Logo
10:24 am - 7:50 pmMDW  Chicago Midway-YWG Winnipeg
9h 26m2 stops Minneapolis St Paul Toronto Pearson Intl
$604WestJet
Sun, Nov 22 - Wed, Dec 2
WestJet Logo
5:00 am - 6:04 pmYWG  Winnipeg-MDW Chicago Midway
13h 04m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
WestJet Logo
10:24 am - 7:50 pmMDW  Chicago Midway-YWG Winnipeg
9h 26m2 stops Minneapolis St Paul Toronto Pearson Intl
$604WestJet
Mon, Nov 23 - Wed, Dec 2
WestJet Logo
5:00 am - 4:18 pmYWG  Winnipeg-MDW Chicago Midway
11h 18m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
WestJet Logo
10:24 am - 7:50 pmMDW  Chicago Midway-YWG Winnipeg
9h 26m2 stops Minneapolis St Paul Toronto Pearson Intl
$604WestJet
Mon, Nov 23 - Wed, Dec 2
WestJet Logo
5:00 am - 4:18 pmYWG  Winnipeg-MDW Chicago Midway
11h 18m2 stops Toronto Pearson Intl Atlanta Hartsfield-Jackson
WestJet Logo
10:24 am - 7:50 pmMDW  Chicago Midway-YWG Winnipeg
9h 26m2 stops Minneapolis St Paul Toronto Pearson Intl
$611WestJet
Sat, Sep 26 - Sat, Oct 3
Porter Airlines Logo
11:15 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
3:20 pm - 5:58 pmMDW  Chicago Midway-YWG Winnipeg
26h 38m2 stops Toronto Island Ottawa
$650Porter Airlines
Sat, Sep 26 - Fri, Oct 2
Porter Airlines Logo
11:15 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
23h 45m2 stops Montreal St Hubert Toronto Island
Porter Airlines Logo
11:45 am - 5:58 pmMDW  Chicago Midway-YWG Winnipeg
30h 13m2 stops Toronto Island Ottawa
$654Porter 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 from Winnipeg to Chicago Midway Airport with more confidence.

What is the cheapest airline to fly from Winnipeg to Chicago Midway Airport?

Delta ($585) and WestJet ($604) are the cheapest airlines to fly round-trip from Winnipeg to Chicago Midway Airport according to KAYAK data over the last 5 days.

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Key details for Winnipeg to Chicago Midway Airport flights

Cheapest flight

$239
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

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

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

  • 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 River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • 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 $401 to $1,537. 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 $272, which is 44% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

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.

Everything you need to know for your flight from Winnipeg to Midway

Information on your arrival and departure airports

Winnipeg (YWG)
Midway (MDW)