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Cheap flights from Winnipeg to Chicago from $192

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Winnipeg to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:55 pm - 11:00 amYWG  Winnipeg-MDW Chicago Midway
15h 05m1 stop Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 12:55 amMDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
$322Multiple Airlines
Fri, Oct 16 - Mon, Oct 19
Multiple Airlines Logo
6:15 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
28h 45m1 stop Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 4:25 pmMDW  Chicago Midway-YWG Winnipeg
25h 05m1 stop Toronto Island
$370Multiple Airlines
Thu, Oct 15 - Sun, Oct 18
Multiple Airlines Logo
9:05 pm - 2:35 pmYWG  Winnipeg-MDW Chicago Midway
17h 30m2 stops Calgary Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 12:55 amMDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
$373Multiple Airlines
Fri, Oct 16 - Mon, Oct 19
Multiple Airlines Logo
6:15 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
28h 45m1 stop Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 12:00 pmMDW  Chicago Midway-YWG Winnipeg
20h 40m2 stops Toronto Island Edmonton
$377Multiple Airlines
Thu, Oct 15 - Sun, Oct 18
Multiple Airlines Logo
4:55 pm - 11:00 amYWG  Winnipeg-MDW Chicago Midway
18h 05m2 stops Calgary Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 12:15 pmMDW  Chicago Midway-YWG Winnipeg
20h 55m2 stops Toronto Island Calgary
$459Multiple Airlines
Thu, Oct 15 - Sun, Oct 18
Multiple Airlines Logo
5:10 pm - 11:00 amYWG  Winnipeg-MDW Chicago Midway
17h 50m1 stop Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 4:25 pmMDW  Chicago Midway-YWG Winnipeg
25h 05m1 stop Toronto Island
$508Multiple Airlines
Sun, Sep 27 - Tue, Sep 29
Multiple Airlines Logo
10:10 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
24h 50m3 stops Calgary Thunder Bay Toronto Island
Multiple Airlines Logo
3:20 pm - 12:15 pmMDW  Chicago Midway-YWG Winnipeg
20h 55m2 stops Toronto Island Calgary
$546Multiple Airlines
Thu, Oct 15 - Sun, Oct 18
Multiple Airlines Logo
10:30 pm - 11:00 amYWG  Winnipeg-MDW Chicago Midway
36h 30m2 stops Edmonton Toronto Pearson Intl
Multiple Airlines Logo
3:20 pm - 12:55 amMDW  Chicago Midway-YWG Winnipeg
9h 35m1 stop Toronto Island
$568Multiple Airlines
Sun, Sep 27 - Tue, Sep 29
Multiple Airlines Logo
10:10 am - 11:00 amYWG  Winnipeg-MDW Chicago Midway
24h 50m3 stops Calgary Montreal Pierre Elliott Trudeau Intl Toronto Island
Multiple Airlines Logo
3:20 pm - 2:05 pmMDW  Chicago Midway-YWG Winnipeg
22h 45m3 stops Toronto Island Montreal Pierre Elliott Trudeau Intl Calgary
$590Multiple Airlines
Thu, Oct 15 - Sun, Oct 18
Multiple Airlines Logo
10:00 am - 9:37 amYWG  Winnipeg-MDW Chicago Midway
23h 37m2 stops Toronto Pearson Intl Detroit Metropolitan Wayne County
Multiple Airlines Logo
9:23 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
17h 17m1 stop Atlanta Hartsfield-Jackson
$633Multiple Airlines
Thu, Dec 17 - Thu, Dec 24

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WestJet flights from Winnipeg to Chicago Midway Airport

Our best WestJet deals on Winnipeg to Chicago Midway Airport flight tickets
WestJet
Dec 17
YWG5:24 pmWinnipeg
23h 26m
1 stop
MDW4:50 pmChicago Midway
Dec 24
MDW9:58 amChicago Midway
28h 42m
1 stop
YWG2:40 pmWinnipeg
$677
WestJet
Nov 20
YWG5:32 pmWinnipeg
23h 07m
1 stop
MDW4:39 pmChicago Midway
Nov 23
MDW5:29 pmChicago Midway
18h 31m
1 stop
YWG12:00 pmWinnipeg
$679
WestJet
Feb 25
YWG6:35 amWinnipeg
5h 16m
1 stop
MDW11:51 amChicago Midway
Feb 28
MDW10:35 amChicago Midway
29h 50m
2 stops
YWG4:25 pmWinnipeg
$686

Porter Airlines flights from Winnipeg to Chicago Midway Airport

Our best Porter Airlines deals on Winnipeg to Chicago Midway Airport flight tickets
Porter Airlines
Oct 14
YWG11:15 amWinnipeg
23h 45m
2 stops
MDW11:00 amChicago Midway
Oct 18
MDW3:20 pmChicago Midway
26h 38m
2 stops
YWG5:58 pmWinnipeg
$712
Porter Airlines
Oct 13
YWG11:40 amWinnipeg
23h 20m
2 stops
MDW11:00 amChicago Midway
Oct 18
MDW3:20 pmChicago Midway
26h 38m
2 stops
YWG5:58 pmWinnipeg
$725

momondo Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Chicago Midway Airport that are best for you.

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Cheapest round-trip
Quickest round-trip

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 10/16

7:55 pm-11:00 am

1 stop15h 05m

Chicago Midway

Mon 10/19

3:20 pm-12:55 am

1 stop9h 35m

$322

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 10/15

6:15 am-11:00 am

1 stop28h 45m

Chicago Midway

Sun 10/18

3:20 pm-4:25 pm

1 stop25h 05m

$370

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 10/16

9:05 pm-2:35 pm

2 stops17h 30m

Chicago Midway

Mon 10/19

3:20 pm-12:55 am

1 stop9h 35m

$373

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 10/15

6:15 am-11:00 am

1 stop28h 45m

Chicago Midway

Sun 10/18

3:20 pm-12:00 pm

2 stops20h 40m

$377

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 10/15

4:55 pm-11:00 am

2 stops18h 05m

Chicago Midway

Sun 10/18

3:20 pm-12:15 pm

2 stops20h 55m

$459

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sun 9/27

5:10 pm-11:00 am

1 stop17h 50m

Chicago Midway

Tue 9/29

3:20 pm-4:25 pm

1 stop25h 05m

$508

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 10/15

10:10 am-11:00 am

3 stops24h 50m

Chicago Midway

Sun 10/18

3:20 pm-12:15 pm

2 stops20h 55m

$546

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Sun 9/27

10:30 pm-11:00 am

2 stops36h 30m

Chicago Midway

Tue 9/29

3:20 pm-12:55 am

1 stop9h 35m

$568

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 10/15

10:10 am-11:00 am

3 stops24h 50m

Chicago Midway

Sun 10/18

3:20 pm-2:05 pm

3 stops22h 45m

$590

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 12/17

10:00 am-9:37 am

2 stops23h 37m

Chicago Midway

Thu 12/24

9:23 pm-2:40 pm

1 stop17h 17m

$633

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Winnipeg to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Winnipeg to Chicago Midway Airport flights?

You could potentially save up to 2% on your flight if you consider stops on a Winnipeg to Chicago Midway Airport flight.

When to book flights from Winnipeg to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Winnipeg to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Winnipeg to Chicago Midway Airport (YWG to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago Midway Airport

Best Price Found

$192

Fastest flight time

5h 18m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Winnipeg in the past 72 hours is $192. The best round-trip flight deal from Winnipeg to Chicago Midway Airport found on momondo in the last 72 hours is $322.
The fastest flight from Winnipeg to Chicago Midway Airport takes 5h 18m
There are no direct flights from Winnipeg to Chicago Midway Airport. There are no popular flight routes from Winnipeg to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Winnipeg to Chicago Midway Airport

  • How far is Winnipeg to Chicago Midway by plane?

    The distance between Winnipeg and Chicago Midway is about 717.8 mi. A reasonable flight in good conditions will take 5h 18m.

  • When did momondo last update prices for flights from Winnipeg Airport to Chicago Midway Airport?

    Prices for flights from Winnipeg Airport to Chicago Midway Airport are updated daily.

  • How old do you have to be to fly from Winnipeg Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Chicago?

Finding the right flight to Chicago from Winnipeg is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Winnipeg to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Winnipeg with this policy.

How can momondo help me find flights from Winnipeg to Chicago?

momondo helps you find the best flight between Winnipeg and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Winnipeg to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Winnipeg to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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