Cheap flights from Winnipeg to Chicago from $266

Round-trip
1 adult
Economy
From?
To?
Tue 10/26
Tue 11/2

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Winnipeg to Chicago.
View current United States travel restrictions

Flight information for Winnipeg to Chicago
(YWG to CHI)

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Chicago
Best Price Found$479The best flight deal from Winnipeg to Chicago found on momondo in the last 72 hours is $479
Fastest flight time4h 11mThe fastest flight from Winnipeg to Chicago takes 4h 11m
Direct flightsNoneThere are no direct flights from Winnipeg to Chicago. Popular non-direct routes for this connection are Winnipeg Airport - Chicago O'Hare Intl Airport and Winnipeg Airport - Chicago Midway Airport.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Winnipeg to Chicago

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

What is the cheapest month to fly from Winnipeg to Chicago?

January

The cheapest time of year to fly to Chicago from Winnipeg is January. Most expensive is August

What is the cheapest day to depart Winnipeg for Chicago?

Wednesday

The cheapest day of the week is typically Wednesday. The most expensive is typically Saturday

When is the cheapest time to fly from Winnipeg to Chicago?

in the afternoon

Winnipeg to Chicago flights are approximately 17% more expensive at noon than in the afternoon

What is the cheapest airline that flies to Chicago from Winnipeg?

United Airlines

United Airlines is the most popular carrier operating from Winnipeg to Chicago

What is the cheapest Winnipeg to Chicago flight route?

Winnipeg - Chicago O'Hare Intl

Fly from Winnipeg to Chicago O'Hare Intl for the best Winnipeg - Chicago flight prices

How far in advance should you book Winnipeg to Chicago flights?

59 days before

The cheapest time to buy a flight from Winnipeg to Chicago is approximately 59 days to departure


Easily compare round-trip flights from Winnipeg to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Winnipeg to Chicago by changing tabs
Air Canada
Nov 30
YWG5:05 amWinnipeg
10h 26m
1 stop
ORD3:31 pmChicago O'Hare Intl
Dec 2
ORD3:45 amChicago O'Hare Intl
7h 27m
1 stop
YWG11:12 amWinnipeg
Delta
Mar 1
YWG2:30 amWinnipeg
4h 29m
1 stop
ORD6:59 amChicago O'Hare Intl
Mar 3
ORD1:30 amChicago O'Hare Intl
5h 20m
1 stop
YWG6:50 amWinnipeg
United Airlines
Nov 18
YWG2:20 amWinnipeg
7h 35m
1 stop
ORD9:55 amChicago O'Hare Intl
Aug 4
ORD4:55 amChicago O'Hare Intl
7h 33m
1 stop
YWG12:28 pmWinnipeg
WestJet
Nov 18
YWG12:00 amWinnipeg
9h 38m
2 stops
ORD9:38 amChicago O'Hare Intl
Aug 4
ORD2:00 amChicago O'Hare Intl
11h 18m
2 stops
YWG1:18 pmWinnipeg
Multiple Airlines
Nov 10
YWG12:00 amWinnipeg
9h 38m
2 stops
ORD9:38 amChicago O'Hare Intl
Nov 10
ORD1:00 pmChicago O'Hare Intl
18h 05m
2 stops
YWG7:05 amWinnipeg
Air Canada
Nov 18
YWG12:45 amWinnipeg
9h 16m
2 stops
ORD10:01 amChicago O'Hare Intl
Aug 4
ORD2:25 amChicago O'Hare Intl
8h 33m
1 stop
YWG10:58 amWinnipeg

Find the cheapest one-way flights from Winnipeg to Chicago

If you're looking for one-way flights from Winnipeg to Chicago, view some of our deals below provided by Air Canada, Delta and United Airlines
Multiple Airlines
Nov 28
YWG1:35 pmWinnipeg
19h 55m
2 stops
MDW9:30 amChicago Midway
United Airlines
Nov 27
YWG2:20 amWinnipeg
7h 35m
1 stop
ORD9:55 amChicago O'Hare Intl
Delta
Nov 27
YWG12:00 amWinnipeg
11h 31m
2 stops
MDW11:31 amChicago Midway

Search last-minute flights to Chicago from Winnipeg

Find and compare flight prices for your last-minute flight from Winnipeg to Chicago
Air Canada
Oct 31
YWG1:30 amWinnipeg
6h 20m
1 stop
ORD7:50 amChicago O'Hare Intl
Nov 13
ORD3:45 amChicago O'Hare Intl
9h 25m
2 stops
YWG1:10 pmWinnipeg
United Airlines
Oct 31
YWG1:30 amWinnipeg
9h 25m
1 stop
ORD10:55 amChicago O'Hare Intl
Nov 13
ORD5:40 amChicago O'Hare Intl
7h 30m
1 stop
YWG1:10 pmWinnipeg
WestJet
Oct 31
YWG12:45 pmWinnipeg
28h 59m
2 stops
ORD5:44 pmChicago O'Hare Intl
Nov 13
ORD5:20 amChicago O'Hare Intl
14h 02m
2 stops
YWG7:22 pmWinnipeg
Multiple Airlines
Oct 26
YWG2:15 amWinnipeg
13h 05m
2 stops
ORD3:20 pmChicago O'Hare Intl
Nov 2
ORD4:51 amChicago O'Hare Intl
9h 33m
2 stops
YWG2:24 pmWinnipeg
Delta
Oct 31
YWG1:00 amWinnipeg
8h 07m
2 stops
MDW9:07 amChicago Midway
Nov 13
MDW4:27 amChicago Midway
10h 39m
2 stops
YWG3:06 pmWinnipeg
United Airlines
Oct 31
YWG1:30 amWinnipeg
9h 25m
1 stop
ORD10:55 amChicago O'Hare Intl
Nov 13
ORD5:40 amChicago O'Hare Intl
7h 30m
1 stop
YWG1:10 pmWinnipeg

Best airlines flying from Winnipeg to Chicago

Compare and see reviews for airlines that fly from Winnipeg to Chicago with momondo
AirlineRatingFree CancellationPrice
United Airlines
PriceFrom $383
Free Cancellation
Rating
6.9
7.3

Boarding

6.7

Comfort

7.5

Crew

6.7

Entertainment

6.2

Food

Reviews

Had to change planes.

1 / 10

  • Are airlines flying from Winnipeg to Chicago offering flexible cancellation due to COVID-19?

    Some of our partner airlines flying from Winnipeg to Chicago are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are United Airlines, Delta, and Air Canada. You can search for the full list of airlines like United Airlines that are offering this flexibility.

  • How far is Winnipeg to Chicago by plane?

    There are 716.4 mi between Winnipeg and Chicago. By plane, this route typically takes 4h 23m.


Can I fly to Chicago from Winnipeg right now?

Information is based on travel restrictions from Winnipeg to Chicago

Most visitors from Winnipeg need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Winnipeg must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Winnipeg are not required to quarantine after entering Chicago.

Can I fly back to Winnipeg from Chicago?

Returning to Winnipeg from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Winnipeg.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Winnipeg.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Similar Winnipeg to Chicago flights

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