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Flights from Chicago to Windsor
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Flights from Chicago to Windsor Starting at NZD 282

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • MDW17:35
        19h 18m
        1 stop
        YQG13:53
        Tue, Mar 11|Chicago - Windsor|Porter Airlines
        NZD 282NZD 554
        49% OFF
        49% OFF
        NZD 554NZD 282

        Choose Porter Airlines flights from Chicago to Windsor. The one-way connecting flight with Porter Airlines departs from Midway International Airport on Tue, Mar 11, arriving at Windsor Airport. One-way Prices start from NZD 282 including taxes and charges.

      • ORD21:12
        15h 41m
        1 stop
        YQG13:53
        Tue, Mar 11|Chicago - Windsor|United Airlines
        NZD 312NZD 554
        44% OFF
        44% OFF
        NZD 554NZD 312

        Choose United Airlines flights from Chicago to Windsor. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Tue, Mar 11, arriving at Windsor Airport. One-way Prices start from NZD 312 including taxes and charges.

      • MDW12:55
        23h 23m
        1 stop
        YQG13:18
        Sat, Mar 1|Chicago - Windsor|Porter Airlines
        NZD 318NZD 554
        42% OFF
        42% OFF
        NZD 554NZD 318

        Choose Porter Airlines flights from Chicago to Windsor. The one-way connecting flight with Porter Airlines departs from Midway International Airport on Sat, Mar 1, arriving at Windsor Airport. One-way Prices start from NZD 318 including taxes and charges.

      • ORD21:12
        15h 6m
        1 stop
        YQG13:18
        Sat, Mar 1|Chicago - Windsor|United Airlines
        NZD 354
        NZD 354

        Choose United Airlines flights from Chicago to Windsor. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Sat, Mar 1, arriving at Windsor Airport. One-way Prices start from NZD 354 including taxes and charges.

      • MDW17:35
        17h 38m
        1 stop
        YQG12:13
        Fri, Mar 21|Chicago - Windsor|Porter Airlines
        NZD 357
        NZD 357

        Choose Porter Airlines flights from Chicago to Windsor. The one-way connecting flight with Porter Airlines departs from Midway International Airport on Fri, Mar 21, arriving at Windsor Airport. One-way Prices start from NZD 357 including taxes and charges.

      • MDW13:05
        22h 8m
        1 stop
        YQG12:13
        Fri, Feb 28|Chicago - Windsor|Porter Airlines
        NZD 368
        NZD 368

        Choose Porter Airlines flights from Chicago to Windsor. The one-way connecting flight with Porter Airlines departs from Midway International Airport on Fri, Feb 28, arriving at Windsor Airport. One-way Prices start from NZD 368 including taxes and charges.

      • MDW11:15
        25h 38m
        1 stop
        YQG13:53
        Tue, Mar 4|Chicago - Windsor|Porter Airlines
        NZD 373
        NZD 373

        Choose Porter Airlines flights from Chicago to Windsor. The one-way connecting flight with Porter Airlines departs from Midway International Airport on Tue, Mar 4, arriving at Windsor Airport. One-way Prices start from NZD 373 including taxes and charges.

      • MDW11:15
        25h 38m
        1 stop
        YQG13:53
        Wed, Mar 5|Chicago - Windsor|Porter Airlines
        NZD 377
        NZD 377

        Choose Porter Airlines flights from Chicago to Windsor. The one-way connecting flight with Porter Airlines departs from Midway International Airport on Wed, Mar 5, arriving at Windsor Airport. One-way Prices start from NZD 377 including taxes and charges.

      • MDW12:55
        23h 23m
        1 stop
        YQG13:18
        Sat, Apr 5|Chicago - Windsor|Porter Airlines
        NZD 400
        NZD 400

        Choose Porter Airlines flights from Chicago to Windsor. The one-way connecting flight with Porter Airlines departs from Midway International Airport on Sat, Apr 5, arriving at Windsor Airport. One-way Prices start from NZD 400 including taxes and charges.

      • ORD18:39
        16h 34m
        1 stop
        YQG12:13
        Fri, Feb 28|Chicago - Windsor|United Airlines
        NZD 408
        NZD 408

        Choose United Airlines flights from Chicago to Windsor. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Feb 28, arriving at Windsor Airport. One-way Prices start from NZD 408 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        YQG02:00 pm
        Tue, Mar 4|Chicago - Windsor|Porter Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Chicago to Windsor flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. AC8958

    Air Canada

    07:20

    ORD

    2.2h

    10:32

    YUL

    SMTWTFS
    Search

  2. AC411

    Air Canada

    12:10

    YUL

    1.4h

    13:36

    YYZ

    SMTWTFS

  3. AC8359

    Air Canada

    16:20

    YYZ

    1.1h

    17:28

    YQG

    SM-WTFS

  4. AC506

    Air Canada

    14:00

    ORD

    1.7h

    16:42

    YYZ

    SMTWTFS
    Search

  5. AC8361

    Air Canada

    20:45

    YYZ

    1.1h

    21:54

    YQG

    ------S

  6. PD2394

    Porter Airlines

    17:20

    MDW

    1.7h

    20:02

    YTZ

    S-T-T-S
    Search

  7. PD2577

    Porter Airlines

    12:15

    YTZ

    1.1h

    13:18

    YQG

    SMTWTFS

  8. UA265

    United Airlines

    17:55

    ORD

    1.8h

    20:44

    YYZ

    SMTWTFS
    Search

  9. TS7183

    Air Transat

    20:55

    YTZ

    1.1h

    21:58

    YQG

    SMTWTFS

  10. UA265

    United Airlines

    17:55

    ORD

    1.8h

    20:44

    YYZ

    SMTWTFS
    Search

  11. PD2577

    Porter Airlines

    12:15

    YTZ

    1.1h

    13:18

    YQG

    SMTWTFS

  12. DL1390

    Delta Air Lines

    19:10

    ORD

    2.3h

    22:29

    LGA

    SMTWTFS
    Search

  13. PD2118

    Porter Airlines

    06:50

    EWR

    1.7h

    08:30

    YTZ

    SMTWTFS

  14. PD2577

    Porter Airlines

    12:15

    YTZ

    1.1h

    13:18

    YQG

    SMTWTFS

  15. AC510

    Air Canada

    20:25

    ORD

    1.7h

    23:07

    YYZ

    SMTWTFS
    Search

  16. AC8353

    Air Canada

    08:20

    YYZ

    1.2h

    09:31

    YQG

    SMTWT-S

  17. B6612

    Jetblue Airways

    20:29

    ORD

    2.5h

    23:58

    BOS

    SMTWTFS
    Search

  18. PD2938

    Porter Airlines

    07:05

    BOS

    2.0h

    09:04

    YTZ

    SMTWTFS

  19. PD2577

    Porter Airlines

    12:15

    YTZ

    1.1h

    13:18

    YQG

    SMTWTFS

  20. UA4631

    United Airlines

    21:12

    ORD

    1.8h

    23:59

    YYZ

    SMTWT-S
    Search

  21. PD2577

    Porter Airlines

    12:15

    YTZ

    1.1h

    13:18

    YQG

    SMTWTFS

  22. UA3495

    United Airlines

    21:12

    ORD

    1.8h

    23:59

    YYZ

    -----F-
    Search

  23. PD2577

    Porter Airlines

    12:15

    YTZ

    1.1h

    13:18

    YQG

    SMTWTFS
Find more flights and airlines

Find the best time to fly from Chicago to Windsor

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

FAQ

  • When are flight tickets from Chicago (CHI) to Windsor (YQG) the cheapest?

    Airlines adjust prices for flights from Chicago to Windsor based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Windsor (YQG) cost?

    According to Trip.com's data, the lowest price is around NZD 683.

How to find a cheap flight from Chicago to Windsor

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Windsor. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Windsor

Cheapest nonstop flight priceNZD 282
Off-season for travelMarch
Peak season for travelNovember
Flight distance388.53 km
Popular airlinePorter Airlines

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