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Flights from Midland to Chicago
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Find Midland to Chicago flights starting at CAD 228.

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

  • One way
  • Round-trip
      • MAF06:00
        7h 14m
        1 stop
        ORD13:14
        Mon, Dec 16|Midland - Chicago|American Airlines
        CAD 228CAD 367
        38% OFF
        38% OFF
        CAD 367CAD 228

        Choose American Airlines flights from Midland to Chicago. The one-way connecting flight with American Airlines departs from Midland International Airport on Mon, Dec 16, arriving at O'Hare International Airport. One-way Prices start from CAD 228 including taxes and charges.

      • MAF06:00
        5h 4m
        1 stop
        ORD11:04
        Sat, Dec 14|Midland - Chicago|American Airlines
        CAD 245CAD 367
        33% OFF
        33% OFF
        CAD 367CAD 245

        Choose American Airlines flights from Midland to Chicago. The one-way connecting flight with American Airlines departs from Midland International Airport on Sat, Dec 14, arriving at O'Hare International Airport. One-way Prices start from CAD 245 including taxes and charges.

      • MAF19:15
        4h 44m
        1 stop
        ORD23:59
        Fri, Dec 13|Midland - Chicago|United Airlines
        CAD 247CAD 367
        33% OFF
        33% OFF
        CAD 367CAD 247

        Choose United Airlines flights from Midland to Chicago. The one-way connecting flight with United Airlines departs from Midland International Airport on Fri, Dec 13, arriving at O'Hare International Airport. One-way Prices start from CAD 247 including taxes and charges.

      • MAF19:15
        4h 44m
        1 stop
        ORD23:59
        Sun, Dec 15|Midland - Chicago|United Airlines
        CAD 247
        CAD 247

        Choose United Airlines flights from Midland to Chicago. The one-way connecting flight with United Airlines departs from Midland International Airport on Sun, Dec 15, arriving at O'Hare International Airport. One-way Prices start from CAD 247 including taxes and charges.

      • MAF07:00
        7h 47m
        1 stop
        ORD14:47
        Sat, Dec 14|Midland - Chicago|United Airlines
        CAD 247
        CAD 247

        Choose United Airlines flights from Midland to Chicago. The one-way connecting flight with United Airlines departs from Midland International Airport on Sat, Dec 14, arriving at O'Hare International Airport. One-way Prices start from CAD 247 including taxes and charges.

      • MAF07:45
        16h 28m
        1 stop
        MDW00:13
        Mon, Dec 16|Midland - Chicago|United Airlines
        CAD 264
        CAD 264

        Choose United Airlines flights from Midland to Chicago. The one-way connecting flight with United Airlines departs from Midland International Airport on Mon, Dec 16, arriving at Midway International Airport. One-way Prices start from CAD 264 including taxes and charges.

      • MAF07:43
        23h 45m
        1 stop
        ORD07:28
        Sun, Dec 15|Midland - Chicago|American Airlines
        CAD 300
        CAD 300

        Choose American Airlines flights from Midland to Chicago. The one-way connecting flight with American Airlines departs from Midland International Airport on Sun, Dec 15, arriving at O'Hare International Airport. One-way Prices start from CAD 300 including taxes and charges.

      • MAF07:45
        8h 5m
        1 stop
        MDW15:50
        Tue, Nov 19|Midland - Chicago|United Airlines
        CAD 302
        CAD 302

        Choose United Airlines flights from Midland to Chicago. The one-way connecting flight with United Airlines departs from Midland International Airport on Tue, Nov 19, arriving at Midway International Airport. One-way Prices start from CAD 302 including taxes and charges.

      • MAF07:00
        7h 40m
        1 stop
        ORD14:40
        Sun, Dec 22|Midland - Chicago|United Airlines
        CAD 311
        CAD 311

        Choose United Airlines flights from Midland to Chicago. The one-way connecting flight with United Airlines departs from Midland International Airport on Sun, Dec 22, arriving at O'Hare International Airport. One-way Prices start from CAD 311 including taxes and charges.

      • MAF13:50
        6h 52m
        1 stop
        MDW20:42
        Mon, Dec 2|Midland - Chicago|United Airlines
        CAD 311
        CAD 311

        Choose United Airlines flights from Midland to Chicago. The one-way connecting flight with United Airlines departs from Midland International Airport on Mon, Dec 2, arriving at Midway International Airport. One-way Prices start from CAD 311 including taxes and charges.

      • MAF13:00
        3h 5m
        Nonstop
        CHI14:00
        Mon, Nov 25|Midland - Chicago|American Airlines
        Find More Flights
        Find More Flights

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

When is the cheapest time to fly from Midland 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.

Find Cheapest Airlines Flying from Midland to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines
From CAD 228
United Airlines
From CAD 247
Delta Air Lines
From CAD 953

Find more flights and airlines

Alternative Routes for Midland to Chicago Flights

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Midland to Chicago.

  • Cheapest
    American Airlines
    MAF
    06:00
    7h 14m
    1 transfer
    ORD
    13:14
    Midland International Airport - O'Hare International Airport
    Mon, Dec 16American Airlines
    CAD 228
  • United Airlines
    MAF
    07:45
    16h 28m
    1 transfer
    MDW
    00:13
    Midland International Airport - Midway International Airport
    Mon, Dec 16United Airlines
    CAD 264
  • United Airlines
    MAF
    07:45
    16h 28m
    1 transfer
    MDW
    00:13
    Midland International Airport - Midway International Airport
    Mon, Dec 16United Airlines
    CAD 264
    Find More Flights

FAQ

  • When are flight tickets from Midland (MAF) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Midland to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from Midland (MAF) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around CAD 634.

  • How long is the flight from Midland (MAF) to Chicago (CHI)?

    It takes about 4 hours 5 minutes to fly from Midland (MAF) to Chicago (CHI).

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

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

  • What are the most popular airlines that fly from Midland (MAF) to Chicago (CHI)?

    Airlines with flights from Midland (MAF) to Chicago (CHI): Southwest Airlines.

  • What's the most popular airline for direct flights from Midland (MAF) to Chicago (CHI)?

    Southwest Airlines operates 1 direct flights from Midland (MAF) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from Midland 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 Midland 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 for Midland to Chicago Flights

Cheapest direct flight priceCAD 227
Off-season travel monthNovember
Peak season for travelAugust
Flight distance1,698.08km
Average flight time4 hours 5 minutes
Popular airlineAmerican Airlines

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