Flights from Orlando to Chicago Starting at NZD 44

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

  • Round-trip
  • One way

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

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  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
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 logo Frontier Airlines Spirit Airlines logo Spirit Airlines

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 490.

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

    It takes around 4 hours 8 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 Intl. 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)?

    Airlines with flights from Orlando (ORL) to Chicago (CHI): Copa Airlines, Southwest Airlines, Iberia, American Airlines, United Airlines, Qatar Airways, Alaska Airlines and Frontier Airlines.

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 one-way flight price NZD 44
Cheapest round-trip ticket price NZD 65
Off-season for travel March
Peak season for travel December
Flight distance 1,588.53 km
Average flight time 4 hours 8 minutes
Popular airline United Airlines

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