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Flights from Windsor to Chicago
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Flights from Windsor to Chicago Starting at NZD 351

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

  • One way
  • Round-trip
      • YQG13:55
        3h 45m
        1 stop
        MDW16:40
        Sun, Mar 2|Windsor - Chicago|Porter Airlines
        NZD 351NZD 503
        30% OFF
        30% OFF
        NZD 503NZD 351

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Sun, Mar 2, arriving at Midway International Airport. One-way Prices start from NZD 351 including taxes and charges.

      • YQG13:55
        3h 45m
        1 stop
        MDW16:40
        Sun, Mar 9|Windsor - Chicago|Porter Airlines
        NZD 363NZD 503
        28% OFF
        28% OFF
        NZD 503NZD 363

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Sun, Mar 9, arriving at Midway International Airport. One-way Prices start from NZD 363 including taxes and charges.

      • YQG14:30
        22h 40m
        1 stop
        MDW12:10
        Mon, Feb 24|Windsor - Chicago|Porter Airlines
        NZD 408NZD 503
        19% OFF
        19% OFF
        NZD 503NZD 408

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Mon, Feb 24, arriving at Midway International Airport. One-way Prices start from NZD 408 including taxes and charges.

      • YQG14:30
        20h 50m
        1 stop
        MDW10:20
        Mon, Mar 3|Windsor - Chicago|Porter Airlines
        NZD 410
        NZD 410

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Mon, Mar 3, arriving at Midway International Airport. One-way Prices start from NZD 410 including taxes and charges.

      • YQG14:30
        22h 40m
        1 stop
        MDW12:10
        Wed, Feb 26|Windsor - Chicago|Air Transat
        NZD 413
        NZD 413

        Choose Air Transat flights from Windsor to Chicago. The one-way connecting flight with Air Transat departs from Windsor Airport on Wed, Feb 26, arriving at Midway International Airport. One-way Prices start from NZD 413 including taxes and charges.

      • YQG13:55
        23h 15m
        1 stop
        MDW12:10
        Sun, Feb 23|Windsor - Chicago|Porter Airlines
        NZD 415
        NZD 415

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Sun, Feb 23, arriving at Midway International Airport. One-way Prices start from NZD 415 including taxes and charges.

      • YQG14:30
        22h 40m
        1 stop
        MDW12:10
        Wed, Feb 26|Windsor - Chicago|Porter Airlines
        NZD 428
        NZD 428

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Wed, Feb 26, arriving at Midway International Airport. One-way Prices start from NZD 428 including taxes and charges.

      • YQG14:30
        22h 40m
        1 stop
        MDW12:10
        Mon, Feb 17|Windsor - Chicago|Porter Airlines
        NZD 431
        NZD 431

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Mon, Feb 17, arriving at Midway International Airport. One-way Prices start from NZD 431 including taxes and charges.

      • YQG14:30
        20h 50m
        1 stop
        MDW10:20
        Tue, Mar 25|Windsor - Chicago|Porter Airlines
        NZD 436
        NZD 436

        Choose Porter Airlines flights from Windsor to Chicago. The one-way connecting flight with Porter Airlines departs from Windsor Airport on Tue, Mar 25, arriving at Midway International Airport. One-way Prices start from NZD 436 including taxes and charges.

      • YQG10:10
        10h 27m
        1 stop
        ORD19:37
        Sun, Mar 23|Windsor - Chicago|Air Canada
        NZD 438
        NZD 438

        Choose Air Canada flights from Windsor to Chicago. The one-way connecting flight with Air Canada departs from Windsor Airport on Sun, Mar 23, arriving at O'Hare International Airport. One-way Prices start from NZD 438 including taxes and charges.

      • YQG01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Sun, Feb 23|Windsor - Chicago|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.

Windsor to Chicago flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. TS7182

    Air Transat

    08:45

    YQG

    1.0h

    09:44

    YTZ

    SMTWTFS
    Search

  2. AA3524

    American Airlines

    06:30

    YYZ

    1.9h

    07:25

    ORD

    SMTWTFS

  3. AC8356

    Air Canada

    10:15

    YQG

    1.0h

    11:17

    YYZ

    SMTW-F-
    Search

  4. AC414

    Air Canada

    14:00

    YYZ

    1.4h

    15:21

    YUL

    SMTWTFS

  5. AC8967

    Air Canada

    18:50

    YUL

    2.6h

    20:25

    ORD

    SMTWTFS

  6. AC8356

    Air Canada

    10:15

    YQG

    1.0h

    11:17

    YYZ

    SMTW-F-
    Search

  7. AC509

    Air Canada

    18:35

    YYZ

    1.9h

    19:32

    ORD

    SMTWTFS

  8. PD2570

    Porter Airlines

    13:50

    YQG

    0.9h

    14:46

    YTZ

    SMTWTFS
    Search

  9. AA3524

    American Airlines

    06:30

    YYZ

    1.9h

    07:25

    ORD

    SMTWTFS

  10. PD2570

    Porter Airlines

    13:50

    YQG

    0.9h

    14:46

    YTZ

    SMTWTFS
    Search

  11. PD653

    Porter Airlines

    07:00

    YYZ

    4.9h

    08:53

    LAS

    SMTWTFS

  12. F92330

    Frontier Airlines

    09:13

    LAS

    3.6h

    14:48

    MDW

    S-TWTFS

  13. PD2570

    Porter Airlines

    13:50

    YQG

    0.9h

    14:46

    YTZ

    SMTWTFS
    Search

  14. PD653

    Porter Airlines

    07:00

    YYZ

    4.9h

    08:53

    LAS

    SMTWTFS

  15. F92146

    Frontier Airlines

    23:25

    LAS

    3.8h

    05:10

    ORD

    SMTWTFS

  16. PD2570

    Porter Airlines

    13:50

    YQG

    0.9h

    14:46

    YTZ

    SMTWTFS
    Search

  17. PD655

    Porter Airlines

    20:05

    YYZ

    4.9h

    21:58

    LAS

    SMTWTFS

  18. UA2102

    United Airlines

    23:50

    LAS

    3.6h

    05:24

    ORD

    SMTWTFS

  19. PD2570

    Porter Airlines

    13:50

    YQG

    0.9h

    14:46

    YTZ

    SMTWTFS
    Search

  20. UA5728

    United Airlines

    21:00

    YYZ

    2.1h

    22:05

    ORD

    SMTWT-S

  21. PD2570

    Porter Airlines

    13:50

    YQG

    0.9h

    14:46

    YTZ

    SMTWTFS
    Search

  22. PD2393

    Porter Airlines

    15:35

    YTZ

    1.8h

    16:24

    MDW

    S--W--S

  23. AC8362

    Air Canada

    18:05

    YQG

    1.1h

    19:08

    YYZ

    SMTWTFS
    Search

  24. PD2387

    Porter Airlines

    11:10

    YTZ

    1.8h

    12:00

    MDW

    SMTWTFS
Find more flights and airlines

Find the best time to fly from Windsor to Chicago

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 Windsor (YQG) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Windsor to Chicago 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 Windsor (YQG) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 654.

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

How to find a cheap flight from Windsor to Chicago

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 Windsor to Chicago. 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 Windsor to Chicago

Cheapest nonstop flight priceNZD 350
Off-season for travelMarch
Peak season for travelNovember
Flight distance388.53 km
Popular airlineAir Transat

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