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Find Midland to Chicago flights starting at CAD 126.

Book one-way or return flights from Midland to Chicago from as little as CAD 126. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip

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

Searching for the best last minute flight from Midland to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Midland to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

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

View airlines operating flights 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 126
United Airlines
From CAD 158
Delta Air Lines
From CAD 279
ANA airlines

Find more flights and airlines

Alternative Routes for Midland to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Midland to Chicago.

  • Cheapest
    American Airlines
    MAF
    16:30
    4h 42m
    1 transfer
    ORD
    21:12
    Midland International Airport - O'Hare International Airport
    Mon, Jul 1American Airlines
    CAD 126
  • United Airlines
    MAF
    13:50
    7h 28m
    1 transfer
    MDW
    21:18
    Midland International Airport - Midway International Airport
    Sat, May 18United Airlines
    CAD 158
  • United Airlines
    MAF
    13:50
    7h 28m
    1 transfer
    MDW
    21:18
    Midland International Airport - Midway International Airport
    Sat, May 18United Airlines
    CAD 158
    Find More Flights

How do I find the cheapest flights?

  • 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 640.
  • 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'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 price

CAD 125

Cheapest month

April

Peak season for travel

October

Flight distance

1,698.08km

Popular airline

American Airlines