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Cheap flights from Winnipeg to Chicago from $207

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
9:35 pm - 11:33 amYWG  Winnipeg-MDW Chicago Midway
14h 58m2 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
$443Multiple Airlines
Fri, Dec 4 - Mon, Dec 7
Multiple Airlines Logo
4:45 pm - 4:07 pmYWG  Winnipeg-MDW Chicago Midway
24h 22m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
5:02 pm - 8:45 pmMDW  Chicago Midway-YWG Winnipeg
26h 43m2 stops Atlanta Hartsfield-Jackson Calgary
$450Multiple Airlines
Thu, Dec 3 - Sun, Dec 6
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
$465Multiple Airlines
Fri, Jan 22 - Tue, Jan 26
Multiple Airlines Logo
9:35 pm - 11:33 amYWG  Winnipeg-MDW Chicago Midway
14h 58m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:52 am - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
30h 48m1 stop Atlanta Hartsfield-Jackson
$475Multiple Airlines
Fri, Dec 11 - Thu, Dec 17
Multiple Airlines Logo
7:00 am - 9:02 pmYWG  Winnipeg-MDW Chicago Midway
15h 02m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:35 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
41h 05m2 stops Orlando Atlanta Hartsfield-Jackson
$510Multiple Airlines
Wed, Dec 16 - Wed, Dec 23
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
$524Multiple Airlines
Fri, Jan 22 - Tue, Jan 26
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 - 8:45 pmMDW  Chicago Midway-YWG Winnipeg
26h 43m2 stops Atlanta Hartsfield-Jackson Calgary
$527Multiple Airlines
Thu, Dec 3 - Sun, Dec 6
Multiple Airlines Logo
9:35 pm - 11:33 amYWG  Winnipeg-MDW Chicago Midway
14h 58m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:11 pm - 1:10 amMDW  Chicago Midway-YWG Winnipeg
29h 59m3 stops Orlando Atlanta Hartsfield-Jackson Calgary
$531Multiple Airlines
Fri, Dec 4 - Mon, Dec 7
Multiple Airlines Logo
9:35 pm - 11:33 amYWG  Winnipeg-MDW Chicago Midway
14h 58m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:43 am - 10:15 amMDW  Chicago Midway-YWG Winnipeg
26h 32m3 stops Atlanta Hartsfield-Jackson Fort Lauderdale Toronto Pearson Intl
$550Multiple Airlines
Fri, Dec 11 - Thu, Dec 17
Multiple Airlines Logo
4:45 pm - 11:33 amYWG  Winnipeg-MDW Chicago Midway
19h 48m2 stops Calgary Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:35 pm - 2:40 pmMDW  Chicago Midway-YWG Winnipeg
17h 05m2 stops Orlando Atlanta Hartsfield-Jackson
$552Multiple Airlines
Fri, Dec 11 - Thu, Dec 17

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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
Nov 29
YWG9:35 pmWinnipeg
19h 43m
2 stops
MDW4:18 pmChicago Midway
Dec 3
MDW12:39 pmChicago Midway
21h 52m
1 stop
YWG11:31 amWinnipeg
$583
WestJet
Nov 29
YWG9:35 pmWinnipeg
19h 43m
2 stops
MDW4:18 pmChicago Midway
Dec 3
MDW12:39 pmChicago Midway
31h 11m
2 stops
YWG8:50 pmWinnipeg
$588
WestJet
Nov 26
YWG9:35 pmWinnipeg
13h 49m
2 stops
MDW10:24 amChicago Midway
Nov 30
MDW10:34 amChicago Midway
12h 59m
1 stop
YWG12:33 amWinnipeg
$596

Delta flights from Winnipeg to Chicago Midway Airport

Our best Delta deals on Winnipeg to Chicago Midway Airport flight tickets
Delta
Dec 6
YWG5:45 pmWinnipeg
20h 16m
2 stops
MDW1:01 pmChicago Midway
Jan 4
MDW1:59 pmChicago Midway
20h 35m
2 stops
YWG11:34 amWinnipeg
$565
Delta
Jan 26
YWG7:15 amWinnipeg
11h 45m
2 stops
MDW6:00 pmChicago Midway
Jan 27
MDW6:40 pmChicago Midway
15h 54m
2 stops
YWG11:34 amWinnipeg
$613
Delta
Jan 26
YWG7:15 amWinnipeg
11h 45m
2 stops
MDW6:00 pmChicago Midway
Jan 27
MDW6:40 pmChicago Midway
15h 54m
2 stops
YWG11:34 amWinnipeg
$614

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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Price

Cheapest round-trip

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 12/4

9:35 pm-11:33 am

2 stops14h 58m

Chicago Midway

Mon 12/7

5:02 pm-5:25 pm

2 stops23h 23m

$443

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 12/3

4:45 pm-4:07 pm

2 stops24h 22m

Chicago Midway

Sun 12/6

5:02 pm-8:45 pm

2 stops26h 43m

$450

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 1/22

7:00 am-11:46 pm

1 stop17h 46m

Chicago Midway

Tue 1/26

1:18 pm-2:40 pm

1 stop24h 22m

$465

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 12/11

9:35 pm-11:33 am

2 stops14h 58m

Chicago Midway

Thu 12/17

6:52 am-2:40 pm

1 stop30h 48m

$475

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Wed 12/16

7:00 am-9:02 pm

1 stop15h 02m

Chicago Midway

Wed 12/23

8:35 pm-2:40 pm

2 stops41h 05m

$510

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 1/22

7:00 am-7:42 pm

2 stops13h 42m

Chicago Midway

Tue 1/26

1:18 pm-2:40 pm

1 stop24h 22m

$524

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Thu 12/3

9:35 pm-4:07 pm

2 stops19h 32m

Chicago Midway

Sun 12/6

5:02 pm-8:45 pm

2 stops26h 43m

$527

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 12/4

9:35 pm-11:33 am

2 stops14h 58m

Chicago Midway

Mon 12/7

6:11 pm-1:10 am

3 stops29h 59m

$531

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 12/11

9:35 pm-11:33 am

2 stops14h 58m

Chicago Midway

Thu 12/17

6:43 am-10:15 am

3 stops26h 32m

$550
Quickest round-trip

WinnipegChicago

YWG Winnipeg - MDW Chicago Midway

YWGMDW

Winnipeg

Fri 12/11

4:45 pm-11:33 am

2 stops19h 48m

Chicago Midway

Thu 12/17

8:35 pm-2:40 pm

2 stops17h 05m

$552

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 5% 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

$207

Fastest flight time

4h 09m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Winnipeg in the past 72 hours is $207. The best round-trip flight deal from Winnipeg to Chicago Midway Airport found on momondo in the last 72 hours is $443.
The fastest flight from Winnipeg to Chicago Midway Airport takes 4h 09m
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 4h 09m.

  • 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
Lansing
Saint Joseph
Benton Harbor
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
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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