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CA $97 Cheap Flights from Orlando (MCO) to Chicago (CHI)

View CA $97 flight on Tue, Feb 9, 2027

Popular airlines from Orlando International Airport (MCO) to Chicago

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

    Prices were available within the past 7 days and start at CA $97 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 5 days ago

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

    Select Frontier Airlines flight, departing Wed, Jan 20 from Orlando to Chicago, returning Sat, Jan 23, priced at CA $193 Found 23 hours ago

    Wed, Jan 20 - Sat, Jan 23 · MCO · ORD · Roundtrip

    Select Frontier Airlines flight, departing Sat, Jan 23 from Orlando to Chicago, returning Sun, Jan 31, priced at CA $194 Found 5 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 5 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 23 hours ago

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

    Select Frontier Airlines flight, departing Sat, Jan 30 from Orlando to Chicago, returning Mon, Feb 1, priced at CA $228 Found 3 days ago

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

    Select Delta flight, departing Tue, Feb 23 from Orlando to Chicago, returning Tue, Mar 9, priced at CA $529 Found 3 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 1 day ago

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

    Select Southwest Airlines flight, departing Sat, Dec 5 from Orlando to Chicago, returning Sun, Dec 6, priced at CA $594 Found 19 hours ago

    Sat, Dec 5 - Sun, Dec 6 · MCO · MDW · Roundtrip

    Select Sun Country Airlines flight, departing Thu, Dec 17 from Orlando to Chicago, returning Mon, Dec 21, priced at CA $647 Found 1 day ago

    Thu, Dec 17 - Mon, Dec 21 · MCO · ORD · Roundtrip

    Alternative airports near Chicago

    Prices were available within the past 7 days. Prices and availability are subject to change.

    Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $910

    23 min

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

    December is typically the cheapest month to fly

    From CA $173 - CA $387 per traveller.

    View flights in December

    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 Intl., MCO 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 $647.

    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

    Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

    Frequently Asked Questions

    How much is a flight from Orlando Intl. Airport to Chicago, IL (CHI-All Airports)?

    Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip flights between MCO and Chicago, IL (CHI-All Airports) start from CA $171. Book today to secure the best price for your trip. Prices and availability are subject to change. Additional terms apply.

    Do I need to pay a cancellation fee if I cancel my flight from MCO to Chicago, IL (CHI-All Airports)?

    This varies between airlines, as each has its own set of terms and conditions. Head to the Customer Service Portal, where there are simple instructions on how to cancel your flight online.

    How do I find cheap flights from MCO to Chicago, IL (CHI-All Airports) that have flexible change policies?

    Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for MCO to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.

    How far is the flight from Orlando Intl. Airport (MCO) to Chicago, IL (CHI-All Airports)?

    The flight distance between Orlando Intl. Airport (MCO) and Chicago, IL (CHI-All Airports) (CHI) is 1,650 kilometers. Listen to your favorite tunes or get stuck into a book and the journey will whiz by.

    Which airlines fly direct from Orlando Intl. Airport (MCO) to Chicago, IL (CHI-All Airports)?

    It's easy to fly directly from MCO to Chicago, IL (CHI-All Airports). Below are some of the most popular carriers that offer nonstop services on this route:

    • Southwest Airlines - (WN) with 247 monthly flights
    • United Airlines - (UA) with 173 monthly flights
    • American Airlines - (AA) with 121 monthly flights
    • Frontier Airlines - (F9) with 82 monthly flights

    Are Orlando Intl. Airport to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?

    Airline tickets from Orlando Intl. Airport to Chicago, IL (CHI-All Airports) are available up to a year before departure on Expedia. And although you may occasionally nab a fantastic last-minute deal, it's never a sure thing. Also, booking your flights ahead of time means you'll have more options — and you can avoid ending up with the dreaded middle seat! We regularly update our fares to bring you the biggest bargains, so check back often for all the latest specials.

    Travel information

    Origin airportOrlando International Airport
    Destination airportChicago Midway Airport
    Distance1,595 km away
    Airlines servingFrontier Airlines, Southwest Airlines, Delta
    Popular airlineFrontier Airlines
    Roundtrip priceCA $171
    Average flight time3 hours 36 mins

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