$190 Find Cheap Flights from Winnipeg to Illinois - Compare and Save

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Price, demand and travel trends for Winnipeg to Illinois flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Winnipeg to Illinois recently?

The cheapest fare from Winnipeg to Illinois in the last week was $376 round-trip, to Chicago O'Hare Intl (ORD).

How do fares into airports in Illinois compare?

According to KAYAK data from the last 12 months, the cheapest airports to fly into Illinois from Winnipeg are:

• Chicago O'Hare Intl (ORD) (avg. price $629)
• Moline Quad-City (MLI) (avg. price $779)
• Chicago Midway (MDW) (avg. price $802)

What's the cheapest month to fly from Winnipeg to Illinois?

May is typically the cheapest month to fly from Winnipeg to Illinois, with round-trip fares averaging $517. October and August are usually the most expensive, averaging $730 and $692, respectively.

How do fares from Winnipeg to Illinois vary by day of the week?

On average, Tuesday is the cheapest day to fly from Winnipeg to Illinois and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 57% more expensive to fly on a Sunday compared to Tuesday.

What's the best time of day to fly from Winnipeg to Illinois?

It's cheapest to fly to Illinois at night with average prices of $432. The afternoon is the most expensive time to fly, with average prices of $733.

What's the best time to book a flight from Winnipeg to Illinois?

Book your flights 23 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 78% compared to booking at the last minute (within 2 weeks of departure).

Key details for Winnipeg to Illinois flights

Low season

February

Cheapest flight

$190
Beat the crowds with an average 60% drop in travelers.
The most popular month to fly with an average 56% increase in travelers.
One-way flight from Winnipeg to Chicago O'Hare Intl Airport

Your Winnipeg to Illinois flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Winnipeg to Illinois?

    Yes. Fares from Winnipeg to Illinois are low right now. As a rule of thumb, a round-trip under $477 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Winnipeg to Illinois?

    Over the past 12 months, round-trip fares from Winnipeg to Illinois have typically cost between $477 and $761.

  • What are the main airports serving Illinois?

    There are 17 airports in Illinois. 80% of KAYAK users choose Chicago O'Hare Intl (ORD) as their arrival airport, while 16% choose Moline Quad-City (MLI).

  • Which airlines fly nonstop from Winnipeg to Illinois?

    Based on the flight schedule for the next 3 months, just one airline regularly flies nonstop from Winnipeg to Illinois: United Airlines.

  • Which destinations in Illinois can I fly nonstop from Winnipeg?

    Based on the flight schedule for the next 3 months, you can fly nonstop from Winnipeg to just one destination in Illinois: Chicago.

  • Is it cheaper to fly with a layover from Winnipeg to Illinois?

    Yes, nonstop flights from Winnipeg to Illinois average $698 over the past 12 months, but flights with a layover can cost less. The most affordable connecting airports are:

    • Calgary (YYC) (avg. price $310)
    • Atlanta Hartsfield-Jackson (ATL) (avg. price $481)
    • Toronto Pearson Intl (YYZ) (avg. price $523)

  • How long is a flight from Winnipeg to Illinois?

    Nonstop flights from Winnipeg to Illinois take 2h 44m on average. All flights fly into Chicago O'Hare Intl (ORD).

  • Which cabin classes are available from Winnipeg to Illinois?

    On flights from Winnipeg to Illinois you can book Economy Class, Business Class or First Class.

  • What are some popular landmarks around Illinois?

    Illinois is home to many popular sights. KAYAK travelers' favorites include:

    • Magnificent Mile
    • Grant Park
    • Soldier Field
    • River North

  • What are the earliest and latest flights from Winnipeg to Illinois?

    The earliest nonstop flight from Winnipeg to Illinois departs at 8:00 am and the latest leaves at 3:15 pm. Nonstop flights take about 2h 44m.

Your guide to booking Winnipeg to Illinois flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 23 weeks before your trip. KAYAK data shows fares in this window are around 78% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • Flexible with your dates? Fly in May to save some money. It's typically the cheapest month on this route, while flights in October will cost you the most.
  • Fly out on a Tuesday to get the cheapest fares. Avoid Sunday flights, which are about 57% more expensive.
  • If you're watching your budget, fly into Chicago O'Hare Intl (ORD) which has the lowest average airfare in the region. Just remember to budget for any onward travel by bus, car or domestic flight.
  • Start your trip in Chicago, the most popular destination in Illinois. From there, it's easy to continue on to other popular spots such as Rosemont, Schaumburg and Champaign.
  • Whether you're trying to save time or money, Chicago O'Hare Intl (ORD) is usually your best option from Winnipeg.

Reviews of the top airlines flying from Winnipeg to Illinois

 
Need help choosing which airline to fly with from Winnipeg to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
United AirlinesOverall score based on 10486 reviews
6.7Food
7.1Entertainment
7.3Comfort
8.1Crew
7.7Boarding
Airline reviews

Went from a plane with free internet to a plane with paid internet. The entertainment screens didn’t work. Crammed in the back and the crew hit my knee with the cart really hard - it hurt. No apologies. I’m still limping today.

4.0 OkayNeil, Nov 2026
Read more United Airlines reviews

Went from a plane with free internet to a plane with paid internet. The entertainment screens didn’t work. Crammed in the back and the crew hit my knee with the cart really hard - it hurt. No apologies. I’m still limping today.

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Reliable, nice crew, I fly often on that flight and I like it all.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

So far so good but food and entertainment are not available for this flight

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Terrible 12 hours delay Terrible We lost our suitcases No medication with us nothing

I like the fact air Canada is on time The food you guys serve is not good

Upgraded to sit at the exit door so good leg room.

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

The plane for my second flight was reassigned. We had to wait for them to get a different plane out of the hangar and call in a crew

Send me 20 dollars and i will do the survey. You survey people think we do things in life to do surveys.

More options for your flight from Winnipeg to Illinois

Complete your trip to Illinois with a hotel stay or car rental