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CA $96 Cheap Flights from Orlando (ORL) to Chicago (CHI)

View CA $96 flight on Wed, Feb 17, 2027

Popular airlines from Orlando Executive Airport (ORL) to Chicago

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  • Cheap Flights from Orlando to Chicago (ORL-CHI)

    Prices were available within the past 7 days and start at CA $96 for one-way flights and CA $171 for roundtrip, for the period specified. Prices and availability are subject to change.

    All deals

    One way

    Roundtrip

    Select Frontier Airlines flight, departing Sat, Jan 23 from Orlando to Chicago, returning Sun, Jan 31, priced at CA $171 Found 4 days ago

    Sat, Jan 23 - Sun, Jan 31 · MCO · MDW · Roundtrip

    Select Frontier Airlines flight, departing Sat, Jan 30 from Orlando to Chicago, returning Tue, Feb 2, priced at CA $192 Found 1 day ago

    Sat, Jan 30 - Tue, Feb 2 · MCO · ORD · Roundtrip

    Select Frontier Airlines flight, departing Sat, Jan 23 from Orlando to Chicago, returning Sun, Jan 31, priced at CA $194 Found 4 days ago

    Sat, Jan 23 - Sun, Jan 31 · MCO · ORD · Roundtrip

    Select Frontier Airlines flight, departing Sat, Jan 23 from Orlando to Chicago, returning Sun, Jan 31, priced at CA $210 Found 4 days ago

    Sat, Jan 23 - Sun, Jan 31 · MCO · MDW · Roundtrip

    Select Frontier Airlines flight, departing Sat, Jan 30 from Orlando to Chicago, returning Mon, Feb 1, priced at CA $214 Found 1 day ago

    Sat, Jan 30 - Mon, Feb 1 · MCO · ORD · Roundtrip

    Select Frontier Airlines flight, departing Wed, Dec 9 from Orlando to Chicago, returning Tue, Dec 15, priced at CA $220 Found 2 days ago

    Wed, Dec 9 - Tue, Dec 15 · MCO · ORD · Roundtrip

    Select American Airlines flight, departing Sat, Jan 30 from Orlando to Chicago, returning Tue, Feb 2, priced at CA $524 Found 1 day ago

    Sat, Jan 30 - Tue, Feb 2 · MCO · ORD · Roundtrip

    Select Delta flight, departing Tue, Feb 23 from Orlando to Chicago, returning Tue, Mar 9, priced at CA $529 Found 2 days ago

    Tue, Feb 23 - Tue, Mar 9 · MCO · MDW · Roundtrip

    Select JetBlue Airways flight, departing Thu, Dec 3 from Orlando to Chicago, returning Tue, Dec 22, priced at CA $556 Found 13 hours ago

    Thu, Dec 3 - Tue, Dec 22 · MCO · ORD · Roundtrip

    Select Southwest Airlines flight, departing Thu, Nov 26 from Orlando to Chicago, returning Mon, Nov 30, priced at CA $573 Found 2 days ago

    Thu, Nov 26 - Mon, Nov 30 · MCO · MDW · Roundtrip

    Find the cheapest month to fly from Orlando (ORL) to Chicago (CHI)

    January is typically the cheapest month to fly

    From CA $174 - CA $408 per traveller.

    View flights in January

    Insights are based on prices from searches for economy trips of 10 days or less on our sites in the last 12 months. Insights are informative only and current prices may differ.

    Book with confidence

    Orlando to Chicago Flights

    The easy way to book your flights from Orlando to Chicago

    With Expedia, it’s simple to find and book flights to Chicago from Orlando whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 6 airlines that cover this route. There are nonstop flights to CHI-All Airports, too.

    Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Orlando to Chicago today, tomorrow, or this week.

    Save dollars with cheap flights from Orlando Executive, ORL to CHI-All Airports, CHI

    Sort your search results by price to find great deals on your flight from Orlando to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Orlando currently is just CA $171 rising to CA $573.

    Here are more money-saving tips:

    • Fly in January when flight prices are normally at their lowest
    • Book about a month to 6 weeks before you travel for the best prices to Chicago
    • Avoid peak season and weekends when flights can cost more
    • Early morning and late-night flights are sometimes cheaper, so try varying your travel times
    • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!

    Reasons to choose Expedia for your flight to Chicago from Orlando

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    Travel information

    Origin airportOrlando Executive Airport
    Destination airportChicago, IL
    Distance1,620 km away
    Roundtrip priceCA $171

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