Cheap flights from Chicago (CHI) to Winnipeg (YWG)
The best prices from Chicago to Winnipeg are usually found in May or October, booked 59 days in advance, depart on a Friday or Saturday and return on a Thursday
How to find the cheapest flight from Chicago (CHI) to Winnipeg (YWG)
All the information you need to plan the best CHI to YWG flight in 2023: compare Chicago to Winnipeg flight prices with the expected peak season, weather and rainfall in Winnipeg.
CHI - YWG Price | $577 - $897 |
|---|---|
YWG Temperature | 3.2 - 68 °F |
YWG Rainfall | 0.8 - 3.1 inches |
| Popular in | March | High demand for flights, 24% potential price rise |
|---|---|---|
| Cheapest in | May | Best time to find cheap flights, 16% potential price drop |
| Round-trip from | $577 | From Chicago (CHI) to Winnipeg |
| One-way from | $226 | One-way flight from Chicago (CHI) to Winnipeg |
What is the cheapest day to fly round-trip from Chicago to Winnipeg?
Tuesday flights are generally found to be more expensive for flights from Chicago to Winnipeg. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Winnipeg.
How far in advance should I book a flight from Chicago to Winnipeg?
To save up to 59% on this flight, we recommend booking at least 60 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Winnipeg from $849 1-2 weeks out and tickets from $1,094 for flights departing within the next 72 hours.
What is the cheapest month to fly from Chicago to Winnipeg?
May can be a great time to fly to Winnipeg from Chicago with a flight ticket averaging about $686. Cheapflights users have found deals in the month of May for as cheap as $433. The most expensive prices can be found in the month of March.
When is the cheapest time to fly from Chicago to Winnipeg (CHI - YWG)?
One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 34% on airfare.
Cheap flights from Chicago to Winnipeg in February, March 2023
The best prices found for CHI to YWG flights for February, March
Chicago O'Hare Intl
Winnipeg
1 stop
18h 44mWinnipeg
Chicago O'Hare Intl
1 stop
11h 43mMultiple Airlines
Chicago O'Hare Intl
Winnipeg
2 stops
25h 15mWinnipeg
Chicago O'Hare Intl
2 stops
21h 42mMultiple Airlines
Chicago O'Hare Intl
Winnipeg
2 stops
22h 03mWinnipeg
Chicago O'Hare Intl
2 stops
26h 09mMultiple Airlines
Chicago to Winnipeg 2023 flight deals
Cheap flights to Winnipeg from Chicago found for this year
Chicago O'Hare Intl
Winnipeg
1 stop
18h 44mWinnipeg
Chicago O'Hare Intl
1 stop
11h 43mMultiple Airlines
Chicago O'Hare Intl
Winnipeg
2 stops
25h 15mWinnipeg
Chicago O'Hare Intl
2 stops
21h 42mMultiple Airlines
Chicago O'Hare Intl
Winnipeg
2 stops
22h 03mWinnipeg
Chicago O'Hare Intl
2 stops
26h 09mMultiple Airlines
Cheap Air Canada flights from Chicago to Winnipeg
Chicago O'Hare Intl
Winnipeg
1 stop
8h 37mWinnipeg
Chicago O'Hare Intl
1 stop
7h 01mAir Canada
Chicago O'Hare Intl
Winnipeg
1 stop
8h 37mWinnipeg
Chicago O'Hare Intl
1 stop
7h 09mAir Canada
Chicago O'Hare Intl
Winnipeg
1 stop
8h 37mWinnipeg
Chicago O'Hare Intl
1 stop
7h 09mAir Canada
Cheap Delta flights from Chicago to Winnipeg
Chicago Midway
Winnipeg
1 stop
5h 44mWinnipeg
Chicago Midway
1 stop
4h 51mDelta
Chicago O'Hare Intl
Winnipeg
1 stop
6h 25mWinnipeg
Chicago O'Hare Intl
1 stop
5h 16mDelta
Chicago Midway
Winnipeg
1 stop
5h 55mWinnipeg
Chicago Midway
2 stops
10h 49mDelta
Last minute flights from Chicago to Winnipeg
Late deals on return flights to Winnipeg from Chicago, departing today and this week
Chicago O'Hare Intl
Winnipeg
3 stops
33h 02mWinnipeg
Chicago O'Hare Intl
1 stop
10h 02mMultiple Airlines
Chicago O'Hare Intl
Winnipeg
1 stop
10h 14mWinnipeg
Chicago O'Hare Intl
1 stop
6h 05mMultiple Airlines
Chicago O'Hare Intl
Winnipeg
2 stops
12h 13mWinnipeg
Chicago O'Hare Intl
2 stops
24h 08mUnited Airlines
One-way flights to Winnipeg from Chicago
The cheapest one-way flights from Chicago to Winnipeg
Chicago O'Hare Intl
Winnipeg
1 stop
6h 27mDelta
Chicago Midway
Winnipeg
1 stop
5h 57mDelta
Chicago O'Hare Intl
Winnipeg
1 stop
13h 53mAir Canada
Reviews of Airlines Servicing Winnipeg
Food
Entertainment
Overall
Boarding
Crew
Comfort
Reviews
Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.
Food
Entertainment
Overall
Boarding
Crew
Comfort
Reviews
Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.
Food
Entertainment
Overall
Boarding
Crew
Comfort
Reviews
Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.
Food
Entertainment
Overall
Boarding
Crew
Comfort
Reviews
Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.
Food
Entertainment
Overall
Boarding
Crew
Comfort
Reviews
Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.
Food
Entertainment
Overall
Boarding
Crew
Comfort
Reviews
Could be better, onboard snacks aren’t enough. A bit of a sandwich or thereabout would suffice.
Related info for your journey
Useful info, stats and facts about Chicago to Winnipeg flights.
What airport do you fly into for flights to Winnipeg from Chicago?
Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 0 inbound flights from Chicago per day from 4 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.
Which airlines flying from Chicago to Winnipeg have flexible cancellations due to COVID-19?
Air Canada, Delta, and United Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.
Can I find flights from Chicago to Winnipeg for under $400 on Cheapflights?
Yes, there are multiple flights from Chicago to Winnipeg for under $400. The cheapest flight booked recently is on Multiple Airlines for just $342, but on average you can expect to pay $417.
Are there last-minute flights available from Chicago to Winnipeg for under $500?
There are currently 8+ open flights from Chicago to Winnipeg within the next 7 days for less than $500.
What are the cheapest airlines flying from Chicago to Winnipeg round-trip?
Flying on Air Canada is currently your cheapest option to Winnipeg, with prices starting at $404. Another option worth looking into is United Airlines, starting at $479 round trip. These flights start at 41% lower than the current average price 3 months from now.
What are the cheapest airlines to fly from Chicago to Winnipeg one-way?
One-way options have recently been found by users for as low as $192 on Delta. Other airlines that offer cheap prices include Air Canada from $226 and United Airlines from $314 one-way.
What are the most popular airlines that fly from Chicago to Winnipeg?
Before booking your flight from Chicago to Winnipeg check out the most popular airlines for this route: Air Canada, Delta or United Airlines.
What are the cheapest flights from Chicago to Winnipeg?
The cheapest flight price from Chicago to Winnipeg is $183. On average you can expect to pay $911. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $342.