Cheap flights from Winnipeg to Chicago

Round-trip
Economy
Winnipeg (YWG)
Chicago (CHI)
Depart
Return
Any month
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The best prices from Winnipeg to Chicago are usually found in January or April, booked 60 days in advance, depart on a Tuesday or Wednesday and return on a Monday

How to find the cheapest flight from
Winnipeg (YWG) to Chicago (CHI)

All the information you need to plan the best YWG to CHI flight in 2022: compare Winnipeg to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
YWG - CHI
Price
C$ 362 - C$ 599
CHI
Temperature
-5 - 23 °C
CHI
Precipitation
43 - 125 mm

Popular in

August

High demand for flights, 28% potential price rise

Cheapest in

January

Best time to find cheap flights, 17% potential price drop

Round-trip from

C$ 454

From Winnipeg to Chicago (CHI)

One-way from

C$ 317

One-way flight from Winnipeg to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
When is the cheapest time to fly from Winnipeg to Chicago (YWG - CHI)?

One of the essential ways to save on airfare from Winnipeg to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 22% on airfare.

What is the cheapest day to fly round-trip from Winnipeg to Chicago?

Monday is generally a great day to depart. Flying on this day could help you save up to 14%.

How far in advance should I book a flight from Winnipeg to Chicago?

Find a great deal and save up to 98% by booking at least 60 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Winnipeg to Chicago within the next two weeks, with the cheapest ticket starting at C$ 734.

Cheap flights from Winnipeg to Chicago in January, February 2022

The best prices found for YWG to CHI flights for January, February
5 Feb - 7 Apr
C$ 522pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
17 Feb - 22 Feb
C$ 535pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YWG
Winnipeg
17 Feb - 22 Feb
C$ 540pp
YWG
Winnipeg
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
   
2 STOPS
YWG
Winnipeg

Winnipeg to Chicago 2022 flight deals

Cheap flights to Chicago from Winnipeg found for this year
3 Mar - 7 Mar
C$ 457pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg
3 Mar - 7 Mar
C$ 457pp
YWG
Winnipeg
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YWG
Winnipeg
3 Mar - 7 Mar
C$ 483pp
YWG
Winnipeg
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
YWG
Winnipeg

Last minute flights from Winnipeg to Chicago

Late deals on round-trip flights to Chicago from Winnipeg, departing today and this week
21 Jan - 24 Jan
C$ 970pp
YWG
Winnipeg
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YWG
Winnipeg
21 Jan - 24 Jan
C$ 994pp
YWG
Winnipeg
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
YWG
Winnipeg
21 Jan - 23 Jan
C$ 997pp
YWG
Winnipeg
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
YWG
Winnipeg

One-way flights to Chicago from Winnipeg

The cheapest one-way flights from Winnipeg to Chicago
3:20 a.m. - 9:40 a.m.
Air Canada
1 stop
6h 20m
YWG - ORD
Air Canada
C$ 317
mytrip.com
2:45 a.m. - 12:52 p.m.
Delta
2 stops
10h 07m
YWG - ORD
Delta
C$ 506
Delta
10:25 a.m. - 9:35 a.m.
Multiple Airlines
3 stops
23h 10m
YWG - MDW
Multiple Airlines
C$ 642
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Winnipeg</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Winnipeg to Chicago

What airport do you fly from for flights from Winnipeg to Chicago?

If you book a flight to Chicago from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 0 flights from Winnipeg to Chicago per day from 4 different airlines.

Which airlines flying from Winnipeg to Chicago have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like United Airlines, Delta, and Air Canada flying from Winnipeg to Chicago have implemented new flexible cancellation policies.

Can I find flights from Winnipeg to Chicago for under C$ 500 on Cheapflights?

Yes, there are multiple flights from Winnipeg to Chicago for under C$ 500. The cheapest flight booked recently is on Delta for just C$ 457, but on average you can expect to pay C$ 585.

Are there last-minute flights available from Winnipeg to Chicago for under C$ 1,000?

There are currently 5+ open flights from Winnipeg to Chicago within the next 7 days for less than C$ 1,000.

What are the cheapest airlines flying from Winnipeg to Chicago round-trip?

Delta, at C$ 457, was found to be the cheapest airline from Winnipeg to Chicago.Alternate airlines to your destination round-trip include Air Canada and United Airlines. Delta is priced at 16% lower than the current average price of a flight leaving 3 months from now.

What are the most popular airlines that fly from Winnipeg to Chicago?

Air Canada, Delta and United Airlines are the most popular airlines when flying from Winnipeg to Chicago.

What are the cheapest flights from Winnipeg to Chicago?

Looking at all options, your cheapest flight can be booked for C$ 451. While the most popular route (Winnipeg - Chicago O'Hare Intl) can be booked for C$ 457 on average our data indicates C$ 458 when flying from Winnipeg to Chicago.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Winnipeg?

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 24 hours before departing to Chicago.

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

Do I need a test to 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) test taken 72 hours before departing to Winnipeg.

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

Hide COVID Travel Restrictions for Chicago, IL

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Winnipeg to Chicago.
Today's exchange rate
C$ 1 = $0.80
Average temperature for January in Chicago
1.0 °C
Avg rainfall for January in Chicago
17.0 mm

Airports servicing Winnipeg

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 4 airlines flying from Winnipeg to Chicago

The chart below displays the airlines Cheapflights users travelling from Winnipeg to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
WestJet
C$ 232 C$ 417 No cancel fee 60%
Search WestJet flights
Delta
C$ 337 C$ 508 No cancel fee N/A
Search Delta flights
Air Canada
C$ 426 C$ 524 No cancel fee 67%
Search Air Canada flights
United Airlines
C$ 460 C$ 630 No cancel fee 69%
Search United Airlines flights
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