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Find Chicago to Brandon flights starting at CAD 631.

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

  • One way
  • Round-trip

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 Chicago to Brandon?

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 Chicago to Brandon

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

Frontier Airlines
From CAD 444
United Airlines
From CAD 536
Jetblue Airways
From CAD 555
WestJet
From CAD 579

Find more flights and airlines

Alternative Routes for Chicago to Brandon Flights

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

  • Cheapest
    Frontier Airlines
    MDW
    16:27
    44h 28m
    2 transfer
    YBR
    12:55
    Midway International Airport - Brandon Airport
    Mon, Jan 27Frontier Airlines
    CAD 444
  • United Airlines
    ORD
    20:29
    40h 26m
    2 transfer
    YBR
    12:55
    O'Hare International Airport - Brandon Airport
    Mon, Jan 27United Airlines
    CAD 536
  • United Airlines
    ORD
    20:29
    40h 26m
    2 transfer
    YBR
    12:55
    O'Hare International Airport - Brandon Airport
    Mon, Jan 27United Airlines
    CAD 536
    Find More Flights

FAQ

  • When are flight tickets from Chicago (CHI) to Brandon (YBR) the cheapest?

    Airlines adjust prices for flights from Chicago to Brandon 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 Chicago (CHI) to Brandon (YBR) cost?

    According to Trip.com's data, the lowest price is around CAD 748.
  • What is the transportation method from the main airport to downtown in Brandon?

    • The distance from Brandon Airport to downtown is about 6km, by taxi about 20 minutes.
  • How many airports in Brandon (YBR)?

    There are 1 airport(s) in Brandon (YBR): Brandon Airport.

How to find a cheap flight from Chicago to Brandon

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 Brandon. 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 Chicago to Brandon Flights

Cheapest direct flight priceCAD 630
Off-season travel monthOctober
Peak season for travelDecember
Flight distance1,302.98km
Popular airlineWestJet