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Flights from Orlando to Chicago
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Flights from Orlando to Chicago Starting at NZD 52

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

  • One way
  • Round-trip
      • Cheapest nonstop
        MCO12:38
        3h 4m
        Nonstop
        MDW14:42
        Fri, Jan 31|Orlando - Chicago|Frontier Airlines
        NZD 52NZD 528
        90% OFF
        90% OFF
        NZD 528NZD 52

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Fri, Jan 31, arriving at Midway International Airport. One-way Prices start from NZD 52 including taxes and charges.

      • MCO18:37
        3h 20m
        Nonstop
        ORD20:57
        Fri, Jan 24|Orlando - Chicago|Frontier Airlines
        NZD 63NZD 528
        88% OFF
        88% OFF
        NZD 528NZD 63

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Fri, Jan 24, arriving at O'Hare International Airport. One-way Prices start from NZD 63 including taxes and charges.

      • MCO07:05
        3h 22m
        Nonstop
        ORD09:27
        Thu, Jan 30|Orlando - Chicago|Frontier Airlines
        NZD 65NZD 528
        88% OFF
        88% OFF
        NZD 528NZD 65

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Thu, Jan 30, arriving at O'Hare International Airport. One-way Prices start from NZD 65 including taxes and charges.

      • MCO07:05
        3h 22m
        Nonstop
        ORD09:27
        Thu, Jan 23|Orlando - Chicago|Frontier Airlines
        NZD 70
        NZD 70

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Thu, Jan 23, arriving at O'Hare International Airport. One-way Prices start from NZD 70 including taxes and charges.

      • MCO07:05
        3h 22m
        Nonstop
        ORD09:27
        Wed, Mar 5|Orlando - Chicago|Frontier Airlines
        NZD 70
        NZD 70

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Wed, Mar 5, arriving at O'Hare International Airport. One-way Prices start from NZD 70 including taxes and charges.

      • MCO08:26
        3h 2m
        Nonstop
        MDW10:28
        Mon, Jan 27|Orlando - Chicago|Frontier Airlines
        NZD 71
        NZD 71

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Mon, Jan 27, arriving at Midway International Airport. One-way Prices start from NZD 71 including taxes and charges.

      • MCO16:37
        3h 17m
        Nonstop
        ORD18:54
        Tue, Mar 18|Orlando - Chicago|Frontier Airlines
        NZD 73
        NZD 73

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Tue, Mar 18, arriving at O'Hare International Airport. One-way Prices start from NZD 73 including taxes and charges.

      • MCO17:12
        3h 3m
        Nonstop
        MDW19:15
        Mon, Feb 24|Orlando - Chicago|Frontier Airlines
        NZD 77
        NZD 77

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Mon, Feb 24, arriving at Midway International Airport. One-way Prices start from NZD 77 including taxes and charges.

      • MCO21:25
        2h 59m
        Nonstop
        MDW23:24
        Tue, Apr 15|Orlando - Chicago|Frontier Airlines
        NZD 78
        NZD 78

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Tue, Apr 15, arriving at Midway International Airport. One-way Prices start from NZD 78 including taxes and charges.

      • MCO16:37
        3h 17m
        Nonstop
        ORD18:54
        Tue, Mar 11|Orlando - Chicago|Frontier Airlines
        NZD 79
        NZD 79

        Choose Frontier Airlines flights from Orlando to Chicago. The one-way direct flight with Frontier Airlines departs from Orlando International Airport on Tue, Mar 11, arriving at O'Hare International Airport. One-way Prices start from NZD 79 including taxes and charges.

      • ORL01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Wed, Jan 22|Orlando - Chicago|Frontier Airlines
        Find More Flights
        Find More Flights

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

Find the best time to fly from Orlando 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.

Airlines Flying from Orlando to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Frontier Airlines logoFrontier AirlinesAmerican Airlines logoAmerican AirlinesSpirit Airlines logoSpirit Airlines

Alternative Routes from Orlando to Chicago

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

  • Cheapest
    Frontier Airlines
    MCO
    12:38
    3h 4m
    Nonstop
    MDW
    14:42
    Orlando International Airport - Midway International Airport
    Fri, Jan 31Frontier Airlines
    NZD 52
  • Frontier Airlines
    MCO
    18:37
    3h 20m
    Nonstop
    ORD
    20:57
    Orlando International Airport - O'Hare International Airport
    Fri, Jan 24Frontier Airlines
    NZD 63
  • Allegiant Air
    SFB
    08:00
    2h 52m
    Nonstop
    RFD
    09:52
    Orlando Sanford International Airport - Chicago Rockford International Airport
    Fri, Jan 24Allegiant Air
    NZD 90
  • Allegiant Air
    SFB
    08:00
    2h 52m
    Nonstop
    RFD
    09:52
    Orlando Sanford International Airport - Chicago Rockford International Airport
    Fri, Jan 24Allegiant Air
    NZD 90
    Find More Flights

FAQ

  • When are flight tickets from Orlando (ORL) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Orlando to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Orlando (ORL) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 360.

  • How long does it take to fly from Orlando (ORL) to Chicago (CHI) and what is the distance?

    It takes around 3 hours 22 minutes to fly from Orlando (ORL) 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 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

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

How to find a cheap flight from Orlando 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 Orlando 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 from Orlando to Chicago

Cheapest nonstop flight priceNZD 52
Cheapest round-trip ticket priceNZD 89
Off-season for travelNovember
Peak season for travelApril
Flight distance1,588.53 km
Average flight time3 hours 22 minutes
Popular airlineFrontier Airlines

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